diff --git a/.nextchanges/bundles/6149.md b/.nextchanges/bundles/6149.md
new file mode 100644
index 00000000000..12bf478ca8d
--- /dev/null
+++ b/.nextchanges/bundles/6149.md
@@ -0,0 +1 @@
+* Bundle file uploads now use the multipart `POST /api/2.0/workspace/import` endpoint instead of the deprecated `POST /api/2.0/workspace-files/import-file`, raising the per-workspace upload rate limit and improving deploy throughput under concurrency. ([#6149](https://github.com/databricks/cli/pull/6149))
diff --git a/acceptance/air/run-submit-deps/output.txt b/acceptance/air/run-submit-deps/output.txt
index 3346fcd06d7..de4c49e1b7f 100644
--- a/acceptance/air/run-submit-deps/output.txt
+++ b/acceptance/air/run-submit-deps/output.txt
@@ -10,9 +10,9 @@ Stream logs after submission using:
   databricks air logs 555
 
 === only config + command are uploaded; no requirements.yaml
->>> print_requests.py //api/2.0/workspace-files/import-file --oneline --sort --unique --keep
-{"method": "POST", "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.air/cli_launch/deps-smoke/deps-smoke_[RUN_ID]/command.sh", "q": {"overwrite": "true"}, "raw_body": "python train.py"}
-{"method": "POST", "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.air/cli_launch/deps-smoke/deps-smoke_[RUN_ID]/training_config.yaml", "q": {"overwrite": "true"}, "raw_body": "experiment_name: deps-smoke\ncommand: python train.py\ncompute:\n    accelerator_type: GPU_1xH100\n    num_accelerators: 1\n    pool_id: capacity-123\nenvironment:\n    version: 5\n    dependencies:\n        - numpy\n        - torch==2.3.0\nmlflow_artifact_location: /Volumes/main/default/air-artifacts\n"}
+>>> print_requests.py //api/2.0/workspace/import --oneline --sort --unique --keep
+{"method": "POST", "path": "/api/2.0/workspace/import", "body": {"multipart_form": {"content": "experiment_name: deps-smoke\ncommand: python train.py\ncompute:\n    accelerator_type: GPU_1xH100\n    num_accelerators: 1\n    pool_id: capacity-123\nenvironment:\n    version: 5\n    dependencies:\n        - numpy\n        - torch==2.3.0\nmlflow_artifact_location: /Volumes/main/default/air-artifacts\n", "format": "AUTO", "overwrite": "true", "path": "/Workspace/Users/[USERNAME]/.air/cli_launch/deps-smoke/deps-smoke_[RUN_ID]/training_config.yaml"}}}
+{"method": "POST", "path": "/api/2.0/workspace/import", "body": {"multipart_form": {"content": "python train.py", "format": "AUTO", "overwrite": "true", "path": "/Workspace/Users/[USERNAME]/.air/cli_launch/deps-smoke/deps-smoke_[RUN_ID]/command.sh"}}}
 
 === inline deps, artifact location, and capacity id reach the submit payload
 >>> print_requests.py //api/2.2/jobs/runs/submit
diff --git a/acceptance/air/run-submit-deps/script b/acceptance/air/run-submit-deps/script
index 422980c99b3..0e8951cae0f 100644
--- a/acceptance/air/run-submit-deps/script
+++ b/acceptance/air/run-submit-deps/script
@@ -2,7 +2,10 @@ title "submit with inline dependencies"
 trace $CLI air run -f run.yaml
 
 title "only config + command are uploaded; no requirements.yaml"
-trace print_requests.py //api/2.0/workspace-files/import-file --oneline --sort --unique --keep
+# Uploads go to POST /workspace/import, which carries the target filename in the
+# multipart body rather than the URL, so each uploaded path shows up under
+# body.multipart_form.path instead of in the request path.
+trace print_requests.py //api/2.0/workspace/import --oneline --sort --unique --keep
 
 title "inline deps, artifact location, and capacity id reach the submit payload"
 trace print_requests.py //api/2.2/jobs/runs/submit
diff --git a/acceptance/air/run-submit-overrides/output.txt b/acceptance/air/run-submit-overrides/output.txt
index 0be49262d1b..19323ff9a50 100644
--- a/acceptance/air/run-submit-overrides/output.txt
+++ b/acceptance/air/run-submit-overrides/output.txt
@@ -13,7 +13,7 @@ Stream logs after submission using:
   databricks air logs 555
 
 === the uploaded config preserves source order and contains overrides
->>> print_requests.py //api/2.0/workspace-files/import-file --oneline --sort --unique
-{"method": "POST", "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.air/cli_launch/overrides-smoke/overrides-smoke_[RUN_ID]/command.sh", "q": {"overwrite": "true"}, "raw_body": "python train.py"}
-{"method": "POST", "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.air/cli_launch/overrides-smoke/overrides-smoke_[RUN_ID]/hyperparameters.yaml", "q": {"overwrite": "true"}, "raw_body": "model:\n    hidden_size: 2048\noptimizer:\n    learning_rate: 0.001\n    name: adamw\n"}
-{"method": "POST", "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.air/cli_launch/overrides-smoke/overrides-smoke_[RUN_ID]/training_config.yaml", "q": {"overwrite": "true"}, "raw_body": "experiment_name: overrides-smoke\ncommand: python train.py\ncompute:\n    accelerator_type: GPU_1xH100\n    num_accelerators: 2\nparameters:\n    model:\n        hidden_size: 2048\n    optimizer:\n        name: adamw\n        learning_rate: 0.001\nmlflow_artifact_location: /Volumes/main/default/air-artifacts\n"}
+>>> print_requests.py //api/2.0/workspace/import --oneline --sort --unique
+{"method": "POST", "path": "/api/2.0/workspace/import", "body": {"multipart_form": {"content": "experiment_name: overrides-smoke\ncommand: python train.py\ncompute:\n    accelerator_type: GPU_1xH100\n    num_accelerators: 2\nparameters:\n    model:\n        hidden_size: 2048\n    optimizer:\n        name: adamw\n        learning_rate: 0.001\nmlflow_artifact_location: /Volumes/main/default/air-artifacts\n", "format": "AUTO", "overwrite": "true", "path": "/Workspace/Users/[USERNAME]/.air/cli_launch/overrides-smoke/overrides-smoke_[RUN_ID]/training_config.yaml"}}}
+{"method": "POST", "path": "/api/2.0/workspace/import", "body": {"multipart_form": {"content": "model:\n    hidden_size: 2048\noptimizer:\n    learning_rate: 0.001\n    name: adamw\n", "format": "AUTO", "overwrite": "true", "path": "/Workspace/Users/[USERNAME]/.air/cli_launch/overrides-smoke/overrides-smoke_[RUN_ID]/hyperparameters.yaml"}}}
+{"method": "POST", "path": "/api/2.0/workspace/import", "body": {"multipart_form": {"content": "python train.py", "format": "AUTO", "overwrite": "true", "path": "/Workspace/Users/[USERNAME]/.air/cli_launch/overrides-smoke/overrides-smoke_[RUN_ID]/command.sh"}}}
diff --git a/acceptance/air/run-submit-overrides/script b/acceptance/air/run-submit-overrides/script
index 263c1920e6c..59234b5e874 100644
--- a/acceptance/air/run-submit-overrides/script
+++ b/acceptance/air/run-submit-overrides/script
@@ -5,4 +5,4 @@ trace $CLI air run -f run.yaml \
   --override parameters.optimizer.learning_rate=0.001
 
 title "the uploaded config preserves source order and contains overrides"
-trace print_requests.py //api/2.0/workspace-files/import-file --oneline --sort --unique
+trace print_requests.py //api/2.0/workspace/import --oneline --sort --unique
diff --git a/acceptance/bin/fault.py b/acceptance/bin/fault.py
index 0aed44d58d1..5b75c0a5907 100755
--- a/acceptance/bin/fault.py
+++ b/acceptance/bin/fault.py
@@ -1,9 +1,11 @@
 #!/usr/bin/env python3
 """Set up a fault rule on the testserver for the current test token.
 
-Usage: fault.py [--after-handler] PATTERN STATUS_CODE OFFSET TIMES [ERROR_CODE]
+Usage: fault.py [--after-handler] [--body-contains SUBSTR] PATTERN STATUS_CODE OFFSET TIMES [ERROR_CODE]
 
   --after-handler  run the handler first; keep its effect and replace only the response
+  --body-contains  only fire when the request body contains SUBSTR, e.g. to target one
+                   file's /workspace/import upload (all uploads share that path)
   PATTERN     HTTP method and path, supports trailing * wildcard,
               e.g. "PUT /api/2.0/permissions/pipelines/*"
   STATUS_CODE HTTP status code to return, e.g. 504
@@ -33,8 +35,17 @@
 if after_handler:
     args.remove("--after-handler")
 
+body_contains = ""
+if "--body-contains" in args:
+    i = args.index("--body-contains")
+    body_contains = args[i + 1]
+    del args[i : i + 2]
+
 if len(args) not in (4, 5):
-    print(f"usage: {sys.argv[0]} [--after-handler] PATTERN STATUS_CODE OFFSET TIMES [ERROR_CODE]", file=sys.stderr)
+    print(
+        f"usage: {sys.argv[0]} [--after-handler] [--body-contains SUBSTR] PATTERN STATUS_CODE OFFSET TIMES [ERROR_CODE]",
+        file=sys.stderr,
+    )
     sys.exit(1)
 
 pattern, status_code, offset, times = args[0], int(args[1]), int(args[2]), int(args[3])
@@ -49,6 +60,7 @@
         "offset": offset,
         "times": times,
         "after_handler": after_handler,
+        "body_contains": body_contains,
     }
 ).encode()
 
diff --git a/acceptance/bundle/apps/app_yaml/out.app.yml.txt b/acceptance/bundle/apps/app_yaml/out.app.yml.txt
index 29cb7da70fa..e79c7a4f57c 100644
--- a/acceptance/bundle/apps/app_yaml/out.app.yml.txt
+++ b/acceptance/bundle/apps/app_yaml/out.app.yml.txt
@@ -1,8 +1,12 @@
 {
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/app/app.yml",
-  "q": {
-    "overwrite": "true"
-  },
-  "raw_body": "command:\n  - python\n  - app.py\n"
+  "path": "/api/2.0/workspace/import",
+  "body": {
+    "multipart_form": {
+      "content": "command:\n  - python\n  - app.py\n",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/app/app.yml"
+    }
+  }
 }
diff --git a/acceptance/bundle/apps/app_yaml/output.txt b/acceptance/bundle/apps/app_yaml/output.txt
index 3554b68f44e..50baf9b4559 100644
--- a/acceptance/bundle/apps/app_yaml/output.txt
+++ b/acceptance/bundle/apps/app_yaml/output.txt
@@ -19,7 +19,7 @@ Created apps.myapp
 Files: 3 uploaded, 0 deleted
 Resources: 1 created, 0 changed, 0 deleted, 0 unchanged
 
->>> jq select(.path | test("app.yml")) [OUTPUT_DIR]/out.requests.txt
+>>> jq select(.body.multipart_form.path | strings | test("app.yml")) [OUTPUT_DIR]/out.requests.txt
 
 >>> [CLI] bundle destroy --auto-approve
 The following resources will be deleted:
diff --git a/acceptance/bundle/apps/app_yaml/script b/acceptance/bundle/apps/app_yaml/script
index 3db6c9e8969..3267d66c598 100644
--- a/acceptance/bundle/apps/app_yaml/script
+++ b/acceptance/bundle/apps/app_yaml/script
@@ -1,7 +1,7 @@
 trace $CLI bundle validate
 trace $CLI bundle plan
 trace $CLI bundle deploy
-trace jq 'select(.path | test("app.yml"))' "$OUT_REQUESTS" | sed 's/\\r//g'  > out.app.yml.txt
+trace jq 'select(.body.multipart_form.path | strings | test("app.yml"))' "$OUT_REQUESTS" | sed 's/\\r//g'  > out.app.yml.txt
 #trace print_requests.py //apps  # currently fails due to TF inserting description=""
 rm "$OUT_REQUESTS"
 
diff --git a/acceptance/bundle/artifacts/ai_runtime_code_source/output.txt b/acceptance/bundle/artifacts/ai_runtime_code_source/output.txt
index 70bbb6eb108..1a3ffc22b37 100644
--- a/acceptance/bundle/artifacts/ai_runtime_code_source/output.txt
+++ b/acceptance/bundle/artifacts/ai_runtime_code_source/output.txt
@@ -16,5 +16,5 @@
 }
 
 === Expecting the code_source tarball to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/code.tgz"
+>>> print_workspace_imports
+/Workspace/foo/bar/artifacts/.internal/code.tgz
diff --git a/acceptance/bundle/artifacts/ai_runtime_code_source/script b/acceptance/bundle/artifacts/ai_runtime_code_source/script
index 396f907033e..32460827ec5 100644
--- a/acceptance/bundle/artifacts/ai_runtime_code_source/script
+++ b/acceptance/bundle/artifacts/ai_runtime_code_source/script
@@ -6,6 +6,6 @@ title "Expecting code_source_path rewritten to the uploaded artifact remote path
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks[].ai_runtime_task' "$OUT_REQUESTS"
 
 title "Expecting the code_source tarball to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep code.tgz | sort
+trace print_workspace_imports | grep code.tgz | sort
 
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/artifact_upload_for_workspace/output.txt b/acceptance/bundle/artifacts/artifact_upload_for_workspace/output.txt
index 2a10679b430..9997818f806 100644
--- a/acceptance/bundle/artifacts/artifact_upload_for_workspace/output.txt
+++ b/acceptance/bundle/artifacts/artifact_upload_for_workspace/output.txt
@@ -48,9 +48,9 @@ Resources: 1 created, 0 changed, 0 deleted, 0 unchanged
 ]
 
 === Expecting wheel to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/source.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source.whl
+/Workspace/foo/bar/artifacts/.internal/source.whl
 
 === Expecting environment dependencies to be updated
 >>> jq -s .[] | select(.path=="/api/2.2/jobs/create") | .body.environments [OUTPUT_DIR]/out.requests.txt
diff --git a/acceptance/bundle/artifacts/artifact_upload_for_workspace/script b/acceptance/bundle/artifacts/artifact_upload_for_workspace/script
index 70c9dffac83..b3c226bc752 100644
--- a/acceptance/bundle/artifacts/artifact_upload_for_workspace/script
+++ b/acceptance/bundle/artifacts/artifact_upload_for_workspace/script
@@ -9,7 +9,7 @@ title "Expecting 2 wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' "$OUT_REQUESTS"
 
 title "Expecting wheel to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 title "Expecting environment dependencies to be updated"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.environments' "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/output.txt b/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/output.txt
index 2419cc5afbc..ca39c787992 100644
--- a/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/output.txt
+++ b/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/output.txt
@@ -4,9 +4,9 @@ Files: 4 uploaded, 0 deleted
 Resources: 0 created, 0 changed, 0 deleted, 0 unchanged
 
 === Expecting wheel to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/source.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source.whl
+/Workspace/foo/bar/artifacts/.internal/source.whl
 
 === Expecting delete request to artifact_path/.internal folder
 >>> jq -s .[] | select(.path=="/api/2.0/workspace/delete") | select(.body.path | test(".*/artifacts/.internal")) [OUTPUT_DIR]/out.requests.txt
diff --git a/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/script b/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/script
index 7ac87760449..0d665cfbc5f 100644
--- a/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/script
+++ b/acceptance/bundle/artifacts/artifact_upload_with_no_library_reference/script
@@ -6,7 +6,7 @@ $CLI bundle plan -o json > tmp.plan.json 2>>LOG.plan
 $CLI bundle deploy $(readplanarg tmp.plan.json)
 
 title "Expecting wheel to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 title "Expecting delete request to artifact_path/.internal folder"
 trace jq -s '.[] | select(.path=="/api/2.0/workspace/delete") | select(.body.path | test(".*/artifacts/.internal"))' "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/upload_multiple_libraries/output.txt b/acceptance/bundle/artifacts/upload_multiple_libraries/output.txt
index ee40963cbaa..e500ebd0342 100644
--- a/acceptance/bundle/artifacts/upload_multiple_libraries/output.txt
+++ b/acceptance/bundle/artifacts/upload_multiple_libraries/output.txt
@@ -38,15 +38,15 @@ Resources: 1 created, 0 changed, 0 deleted, 0 unchanged
 ]
 
 === Expecting 4 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source1.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source2.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source3.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source4.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/source1.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/source2.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/source3.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/artifacts/.internal/source4.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source1.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source2.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source3.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/whl/source4.whl
+/Workspace/foo/bar/artifacts/.internal/source1.whl
+/Workspace/foo/bar/artifacts/.internal/source2.whl
+/Workspace/foo/bar/artifacts/.internal/source3.whl
+/Workspace/foo/bar/artifacts/.internal/source4.whl
 
 === Expecting environment dependencies to be updated
 >>> jq -s .[] | select(.path=="/api/2.2/jobs/create") | .body.environments [OUTPUT_DIR]/out.requests.txt
diff --git a/acceptance/bundle/artifacts/upload_multiple_libraries/script b/acceptance/bundle/artifacts/upload_multiple_libraries/script
index f65f8154f2a..89d0ba55291 100644
--- a/acceptance/bundle/artifacts/upload_multiple_libraries/script
+++ b/acceptance/bundle/artifacts/upload_multiple_libraries/script
@@ -12,7 +12,7 @@ title "Expecting 5 wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' "$OUT_REQUESTS"
 
 title "Expecting 4 wheels to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 title "Expecting environment dependencies to be updated"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.environments' "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/whl_change_version/output.txt b/acceptance/bundle/artifacts/whl_change_version/output.txt
index 34b272c0f08..30134175168 100644
--- a/acceptance/bundle/artifacts/whl_change_version/output.txt
+++ b/acceptance/bundle/artifacts/whl_change_version/output.txt
@@ -29,19 +29,19 @@ dist/my_test_code-0.1.0-py3-none-any.whl
 ]
 
 === Expecting 1 wheel to be uploaded
->>> jq .path [OUTPUT_DIR]/out.requests.txt
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.1.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/.gitignore"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/databricks.yml"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.1.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/__init__.py"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/__main__.py"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/setup.py"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/STATE_FILENAME"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.1.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/.gitignore
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/databricks.yml
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.1.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/__init__.py
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/__main__.py
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/setup.py
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/STATE_FILENAME
 
 >>> update_file.py my_test_code/__init__.py 0.1.0 0.2.0
 
@@ -62,14 +62,14 @@ dist/my_test_code-0.2.0-py3-none-any.whl
 json[0].libraries[0].whl = "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.2.0-py3-none-any.whl";
 
 === Expecting 1 wheel to be uploaded
->>> jq .path [OUTPUT_DIR]/out.requests.txt
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.2.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.2.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/__init__.py"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/STATE_FILENAME"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.2.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.2.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/__init__.py
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/STATE_FILENAME
 
 === Restore config to target old wheel
 >>> update_file.py databricks.yml ./dist/*.whl ./dist/my*0.1.0*.whl
@@ -92,12 +92,12 @@ dist/my_test_code-0.2.0-py3-none-any.whl
 json[0].libraries[0].whl = "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.1.0-py3-none-any.whl";
 
 === Expecting 1 wheel to be uploaded
->>> jq .path [OUTPUT_DIR]/out.requests.txt
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.1.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.2.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/databricks.yml"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.2.0-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/STATE_FILENAME"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.1.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.2.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/databricks.yml
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.2.0-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/STATE_FILENAME
diff --git a/acceptance/bundle/artifacts/whl_change_version/script b/acceptance/bundle/artifacts/whl_change_version/script
index 49d50f0b0b5..4b97cb54259 100644
--- a/acceptance/bundle/artifacts/whl_change_version/script
+++ b/acceptance/bundle/artifacts/whl_change_version/script
@@ -6,7 +6,7 @@ title "Expecting 1 wheel in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' "$OUT_REQUESTS"
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path "$OUT_REQUESTS" | grep import | sort
+trace print_workspace_imports | sort
 
 rm "$OUT_REQUESTS"
 
@@ -20,7 +20,7 @@ title "Expecting 1 wheel in libraries section in /jobs/reset"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/reset") | .body.new_settings.tasks' "$OUT_REQUESTS" | gron.py | grep -w libraries
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path "$OUT_REQUESTS" | grep import | sort
+trace print_workspace_imports | sort
 
 rm "$OUT_REQUESTS"
 
@@ -34,6 +34,6 @@ title "Expecting 1 wheel in libraries section in /jobs/reset"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/reset") | .body.new_settings.tasks' "$OUT_REQUESTS" | gron.py | grep -w libraries
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path "$OUT_REQUESTS" | grep import | sort
+trace print_workspace_imports | sort
 
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/whl_dbfs/output.txt b/acceptance/bundle/artifacts/whl_dbfs/output.txt
index b4974a6f5ca..04b3a0f58fa 100644
--- a/acceptance/bundle/artifacts/whl_dbfs/output.txt
+++ b/acceptance/bundle/artifacts/whl_dbfs/output.txt
@@ -25,6 +25,6 @@ Resources: 1 created, 0 changed, 0 deleted, 0 unchanged
 ]
 
 === Expecting no wheels to be uploaded
->>> errcode sh -c jq .path < "$OUT_REQUESTS" | grep import | grep whl
+>>> print_workspace_imports
 
 Exit code: 1
diff --git a/acceptance/bundle/artifacts/whl_dbfs/script b/acceptance/bundle/artifacts/whl_dbfs/script
index 944ecf709f9..bd7b88b5806 100644
--- a/acceptance/bundle/artifacts/whl_dbfs/script
+++ b/acceptance/bundle/artifacts/whl_dbfs/script
@@ -8,6 +8,6 @@ title "Expecting 1 wheel in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' "$OUT_REQUESTS"
 
 title "Expecting no wheels to be uploaded"
-trace errcode sh -c 'jq .path < "$OUT_REQUESTS" | grep import | grep whl'
+trace print_workspace_imports | errcode grep whl
 
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/whl_dynamic/output.txt b/acceptance/bundle/artifacts/whl_dynamic/output.txt
index 51be24e7e43..3461014160d 100644
--- a/acceptance/bundle/artifacts/whl_dynamic/output.txt
+++ b/acceptance/bundle/artifacts/whl_dynamic/output.txt
@@ -48,11 +48,11 @@ json[1].libraries[0].whl = "/Workspace/Users/[USERNAME]/.bundle/test-bundle/defa
 json[1].libraries[1].whl = "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl";
 
 === Expecting 2 patched wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][1]-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/prebuilt/other_test_code-0.0.1-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][1]-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/prebuilt/other_test_code-0.0.1-py3-none-any.whl
 
 === Updating the local wheel and deploying again
 
@@ -74,7 +74,7 @@ json[1].libraries[0].whl = "/Workspace/Users/[USERNAME]/.bundle/test-bundle/defa
 json[1].libraries[1].whl = "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl";
 
 === Expecting 2 pached wheels to be uploaded (Bad: it is currently uploaded twice)
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][2]-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][2]-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_dynamic/script b/acceptance/bundle/artifacts/whl_dynamic/script
index b73202a65ec..d031d02715c 100644
--- a/acceptance/bundle/artifacts/whl_dynamic/script
+++ b/acceptance/bundle/artifacts/whl_dynamic/script
@@ -22,7 +22,7 @@ title "Expecting 2 patched wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' "$OUT_REQUESTS" | gron.py | grep -w libraries
 
 title "Expecting 2 patched wheels to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 rm "$OUT_REQUESTS"
 
@@ -40,4 +40,4 @@ title "Expecting 2 patched wheels in libraries section in /jobs/reset"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/reset") | .body.new_settings.tasks' "$OUT_REQUESTS" | gron.py | grep -w libraries
 
 title "Expecting 2 pached wheels to be uploaded (Bad: it is currently uploaded twice)"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
diff --git a/acceptance/bundle/artifacts/whl_explicit/output.txt b/acceptance/bundle/artifacts/whl_explicit/output.txt
index 55aa3ff229a..14358c0ab32 100644
--- a/acceptance/bundle/artifacts/whl_explicit/output.txt
+++ b/acceptance/bundle/artifacts/whl_explicit/output.txt
@@ -21,9 +21,9 @@ my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
 ]
 
 === Expecting 1 wheel to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
 
 === Expecting delete request to artifact_path/.internal folder
 >>> jq -s .[] | select(.path=="/api/2.0/workspace/delete") | select(.body.path | test(".*/artifacts/.internal")) [OUTPUT_DIR]/out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_explicit/script b/acceptance/bundle/artifacts/whl_explicit/script
index f55d7da467a..a1227cd125d 100644
--- a/acceptance/bundle/artifacts/whl_explicit/script
+++ b/acceptance/bundle/artifacts/whl_explicit/script
@@ -8,7 +8,7 @@ title "Expecting 1 wheel in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' "$OUT_REQUESTS"
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 title "Expecting delete request to artifact_path/.internal folder"
 trace jq -s '.[] | select(.path=="/api/2.0/workspace/delete") | select(.body.path | test(".*/artifacts/.internal"))' "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/whl_implicit/output.txt b/acceptance/bundle/artifacts/whl_implicit/output.txt
index d589ebc5d74..c610058f32f 100644
--- a/acceptance/bundle/artifacts/whl_implicit/output.txt
+++ b/acceptance/bundle/artifacts/whl_implicit/output.txt
@@ -21,6 +21,6 @@ dist/my_test_code-0.0.1-py3-none-any.whl
 ]
 
 === Expecting 1 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_implicit/script b/acceptance/bundle/artifacts/whl_implicit/script
index a42ce2844db..8124726f4ff 100644
--- a/acceptance/bundle/artifacts/whl_implicit/script
+++ b/acceptance/bundle/artifacts/whl_implicit/script
@@ -8,6 +8,6 @@ title "Expecting 1 wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' "$OUT_REQUESTS"
 
 title "Expecting 1 wheels to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/whl_implicit_custom_path/output.txt b/acceptance/bundle/artifacts/whl_implicit_custom_path/output.txt
index 04683b58ffc..1a93fb8c9bd 100644
--- a/acceptance/bundle/artifacts/whl_implicit_custom_path/output.txt
+++ b/acceptance/bundle/artifacts/whl_implicit_custom_path/output.txt
@@ -39,6 +39,6 @@ package/my_test_code-0.0.1-py3-none-any.whl
 }
 
 === Expecting 1 wheel to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/package/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/foo/bar/.internal/my_test_code-0.0.1-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/package/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/foo/bar/.internal/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_implicit_custom_path/script b/acceptance/bundle/artifacts/whl_implicit_custom_path/script
index 410957d8233..4d5fd31d6e7 100644
--- a/acceptance/bundle/artifacts/whl_implicit_custom_path/script
+++ b/acceptance/bundle/artifacts/whl_implicit_custom_path/script
@@ -7,6 +7,6 @@ title "Expecting 1 wheel in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body' "$OUT_REQUESTS" | nostamp
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/whl_implicit_notebook/output.txt b/acceptance/bundle/artifacts/whl_implicit_notebook/output.txt
index 4172ddf8f51..6a49d1e1889 100644
--- a/acceptance/bundle/artifacts/whl_implicit_notebook/output.txt
+++ b/acceptance/bundle/artifacts/whl_implicit_notebook/output.txt
@@ -11,6 +11,6 @@ dist/my_test_code-0.0.1-py3-none-any.whl
 ]
 
 === Expecting 1 wheel to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_implicit_notebook/script b/acceptance/bundle/artifacts/whl_implicit_notebook/script
index 72d0ce55360..41bae0e4237 100644
--- a/acceptance/bundle/artifacts/whl_implicit_notebook/script
+++ b/acceptance/bundle/artifacts/whl_implicit_notebook/script
@@ -8,6 +8,6 @@ title "Expecting 1 wheel in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks[0].libraries' "$OUT_REQUESTS"
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/whl_multiple/output.txt b/acceptance/bundle/artifacts/whl_multiple/output.txt
index 8bf5bef423d..96edc8e5c85 100644
--- a/acceptance/bundle/artifacts/whl_multiple/output.txt
+++ b/acceptance/bundle/artifacts/whl_multiple/output.txt
@@ -25,8 +25,8 @@ my_test_code/dist/my_test_code_2-0.0.1-py3-none-any.whl
 ]
 
 === Expecting 2 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code_2-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code_2-0.0.1-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code_2-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code_2-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_multiple/script b/acceptance/bundle/artifacts/whl_multiple/script
index df8ad98b3c4..8c06cd32454 100644
--- a/acceptance/bundle/artifacts/whl_multiple/script
+++ b/acceptance/bundle/artifacts/whl_multiple/script
@@ -8,6 +8,6 @@ title "Expecting 2 wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' "$OUT_REQUESTS"
 
 title "Expecting 2 wheels to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 rm -fr "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/whl_no_cleanup/output.txt b/acceptance/bundle/artifacts/whl_no_cleanup/output.txt
index a61388c76f9..b80a0145ad1 100644
--- a/acceptance/bundle/artifacts/whl_no_cleanup/output.txt
+++ b/acceptance/bundle/artifacts/whl_no_cleanup/output.txt
@@ -3,9 +3,9 @@
 dist/my_test_code-0.0.1-py3-none-any.whl
 
 === Expecting 1 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl
 
 === No calls to delete internal folder expected
 >>> jq -s .[] | select(.path=="/api/2.0/workspace/delete") | select(.body.path | test(".*/artifacts/.internal")) [OUTPUT_DIR]/out.requests.txt
diff --git a/acceptance/bundle/artifacts/whl_no_cleanup/script b/acceptance/bundle/artifacts/whl_no_cleanup/script
index f3ef86ecf70..6a4a10bc75e 100644
--- a/acceptance/bundle/artifacts/whl_no_cleanup/script
+++ b/acceptance/bundle/artifacts/whl_no_cleanup/script
@@ -5,7 +5,7 @@ cat LOG.deploy | contains.py "my_test_code-0.0.1-py3-none-any.whl" > /dev/null
 trace find.py --expect 1 whl
 
 title "Expecting 1 wheels to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 $CLI bundle plan -o json > tmp.plan.json 2>>LOG.plan
 $CLI bundle deploy $(readplanarg tmp.plan.json) &> LOG.redeploy
diff --git a/acceptance/bundle/artifacts/whl_prebuilt_multiple/output.txt b/acceptance/bundle/artifacts/whl_prebuilt_multiple/output.txt
index e43ce01f38c..c18e0b2d6da 100644
--- a/acceptance/bundle/artifacts/whl_prebuilt_multiple/output.txt
+++ b/acceptance/bundle/artifacts/whl_prebuilt_multiple/output.txt
@@ -36,8 +36,8 @@ dist/my_test_code-0.0.1-py3-none-any.whl
 ]
 
 === Expecting 2 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/lib/other_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/other_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/lib/other_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/dist/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_prebuilt_multiple/script b/acceptance/bundle/artifacts/whl_prebuilt_multiple/script
index 2b9240de98a..8034c3171cf 100644
--- a/acceptance/bundle/artifacts/whl_prebuilt_multiple/script
+++ b/acceptance/bundle/artifacts/whl_prebuilt_multiple/script
@@ -10,6 +10,6 @@ title "Expecting 2 wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' "$OUT_REQUESTS"
 
 title "Expecting 2 wheels to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/whl_prebuilt_outside/output.txt b/acceptance/bundle/artifacts/whl_prebuilt_outside/output.txt
index 9611c9541f2..a034c80a088 100644
--- a/acceptance/bundle/artifacts/whl_prebuilt_outside/output.txt
+++ b/acceptance/bundle/artifacts/whl_prebuilt_outside/output.txt
@@ -32,6 +32,6 @@ Resources: 1 created, 0 changed, 0 deleted, 0 unchanged
 ]
 
 === Expecting 2 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/other_test_code-0.0.1-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/other_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_prebuilt_outside/script b/acceptance/bundle/artifacts/whl_prebuilt_outside/script
index ecfd7bea799..23a2e0fc1ef 100644
--- a/acceptance/bundle/artifacts/whl_prebuilt_outside/script
+++ b/acceptance/bundle/artifacts/whl_prebuilt_outside/script
@@ -11,6 +11,6 @@ title "Expecting 2 wheels in libraries section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' "$OUT_REQUESTS"
 
 title "Expecting 2 wheels to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/output.txt b/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/output.txt
index 324b0a1b18a..b26bae880f5 100644
--- a/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/output.txt
+++ b/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/output.txt
@@ -56,6 +56,6 @@ Resources: 1 created, 0 changed, 0 deleted, 0 unchanged
 ]
 
 === Expecting 2 wheels to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][1]-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/python-wheel/default/artifacts/.internal/other_test_code-0.0.1+[UNIX_TIME_NANOS][1]-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/script b/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/script
index b53c1dc55b2..f972cf2504e 100644
--- a/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/script
+++ b/acceptance/bundle/artifacts/whl_prebuilt_outside_dynamic/script
@@ -14,6 +14,6 @@ trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.tasks' "$OUT_RE
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body.environments' "$OUT_REQUESTS"
 
 title "Expecting 2 wheels to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/whl_via_environment_key/output.txt b/acceptance/bundle/artifacts/whl_via_environment_key/output.txt
index eb0d23431f3..f6ba380bc11 100644
--- a/acceptance/bundle/artifacts/whl_via_environment_key/output.txt
+++ b/acceptance/bundle/artifacts/whl_via_environment_key/output.txt
@@ -41,6 +41,6 @@ my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
 }
 
 === Expecting 1 wheel to be uploaded
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_via_environment_key/script b/acceptance/bundle/artifacts/whl_via_environment_key/script
index d7657fa4b4f..09f9ed82c47 100644
--- a/acceptance/bundle/artifacts/whl_via_environment_key/script
+++ b/acceptance/bundle/artifacts/whl_via_environment_key/script
@@ -8,6 +8,6 @@ title "Expecting 1 wheel in environments section in /jobs/create"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body' "$OUT_REQUESTS" | nostamp
 
 title "Expecting 1 wheel to be uploaded"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/artifacts/whl_via_environment_key_extras/output.txt b/acceptance/bundle/artifacts/whl_via_environment_key_extras/output.txt
index 39e7ead5144..e99a248c94b 100644
--- a/acceptance/bundle/artifacts/whl_via_environment_key_extras/output.txt
+++ b/acceptance/bundle/artifacts/whl_via_environment_key_extras/output.txt
@@ -41,5 +41,5 @@ my_test_code/dist/my_test_code-0.0.1-py3-none-any.whl
 }
 
 === Expecting 1 wheel to be uploaded under its bare filename (no extras)
->>> jq .path
-"/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl"
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal/my_test_code-0.0.1-py3-none-any.whl
diff --git a/acceptance/bundle/artifacts/whl_via_environment_key_extras/script b/acceptance/bundle/artifacts/whl_via_environment_key_extras/script
index dadef34e181..157472b5f55 100644
--- a/acceptance/bundle/artifacts/whl_via_environment_key_extras/script
+++ b/acceptance/bundle/artifacts/whl_via_environment_key_extras/script
@@ -8,6 +8,6 @@ title "Expecting the environments dependency to keep its [train] extras suffix"
 trace jq -s '.[] | select(.path=="/api/2.2/jobs/create") | .body' "$OUT_REQUESTS" | nostamp
 
 title "Expecting 1 wheel to be uploaded under its bare filename (no extras)"
-trace jq .path < "$OUT_REQUESTS" | grep import | grep whl | sort
+trace print_workspace_imports | grep whl | sort
 
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/deploy/partial-summary-on-push-fail/output.txt b/acceptance/bundle/deploy/partial-summary-on-push-fail/output.txt
index a97e8642981..4610f302b33 100644
--- a/acceptance/bundle/deploy/partial-summary-on-push-fail/output.txt
+++ b/acceptance/bundle/deploy/partial-summary-on-push-fail/output.txt
@@ -3,7 +3,7 @@
 Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files...
 Error: access denied: /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/resources.json (403 INJECTED)
 
-Endpoint: POST [DATABRICKS_URL]/api/2.0/workspace-files/import-file/Workspace%2FUsers%2F[USERNAME]%2F.bundle%2Ftest-bundle%2Fdefault%2Fstate%2Fresources.json?overwrite=true
+Endpoint: POST [DATABRICKS_URL]/api/2.0/workspace/import
 HTTP Status: 403 Forbidden
 API error_code: INJECTED
 API message: Fault injected by test.
diff --git a/acceptance/bundle/deploy/partial-summary-on-push-fail/script b/acceptance/bundle/deploy/partial-summary-on-push-fail/script
index bc36c59cacc..d2fef85a1d7 100644
--- a/acceptance/bundle/deploy/partial-summary-on-push-fail/script
+++ b/acceptance/bundle/deploy/partial-summary-on-push-fail/script
@@ -9,7 +9,7 @@ trap cleanup EXIT
 # Inject a 403 on the resource-state upload (PushResourcesState). The files are
 # uploaded by then, so "Files:" still reports them; "Resources:" must NOT print,
 # because this fails before planning and there are no resource counts to report.
-fault.py "POST /api/2.0/workspace-files/import-file/Workspace/Users/$CURRENT_USER_NAME/.bundle/test-bundle/default/state/resources.json" 403 0 1
+fault.py --body-contains "state/resources.json" "POST /api/2.0/workspace/import" 403 0 1
 
 # -q: the state-push 403 races resource apply, so whether "Created jobs.my_job" is
 # emitted before the failure is platform-dependent. This test asserts Files is reported
diff --git a/acceptance/bundle/deploy/partial-summary-on-push-fail/test.toml b/acceptance/bundle/deploy/partial-summary-on-push-fail/test.toml
index 01dc2713a99..64cb4896dce 100644
--- a/acceptance/bundle/deploy/partial-summary-on-push-fail/test.toml
+++ b/acceptance/bundle/deploy/partial-summary-on-push-fail/test.toml
@@ -1,5 +1,5 @@
 # The resource summary must not print when pushing resource state fails, so the
-# fault is injected on the state upload (POST import-file). The path is fixed, so
+# fault is injected on the state upload (POST /workspace/import). The path is fixed, so
 # the bundle name must be stable (test-bundle, not $UNIQUE_NAME).
 #
 # The injected path is the direct-engine state file (state/resources.json), so
diff --git a/acceptance/bundle/deploy/readplan/whl-upload/output.txt b/acceptance/bundle/deploy/readplan/whl-upload/output.txt
index 48212c57e37..6b21d59c6b0 100644
--- a/acceptance/bundle/deploy/readplan/whl-upload/output.txt
+++ b/acceptance/bundle/deploy/readplan/whl-upload/output.txt
@@ -7,14 +7,8 @@ Created jobs.my_job
 Files: 2 uploaded, 0 deleted
 Resources: 1 created, 0 changed, 0 deleted, 0 unchanged
 
->>> print_requests.py //artifacts/.internal --del-field raw_body
-{
-  "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/whl-upload/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl",
-  "q": {
-    "overwrite": "true"
-  }
-}
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/whl-upload/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl
 
 >>> [CLI] bundle destroy --auto-approve
 The following resources will be deleted:
@@ -32,14 +26,8 @@ Created jobs.my_job
 Files: 4 uploaded, 0 deleted
 Resources: 1 created, 0 changed, 0 deleted, 0 unchanged
 
->>> print_requests.py //artifacts/.internal --del-field raw_body
-{
-  "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/whl-upload/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl",
-  "q": {
-    "overwrite": "true"
-  }
-}
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/whl-upload/default/artifacts/.internal/my_test_code-0.0.1+[UNIX_TIME_NANOS][0]-py3-none-any.whl
 
 >>> [CLI] bundle destroy --auto-approve
 The following resources will be deleted:
diff --git a/acceptance/bundle/deploy/readplan/whl-upload/script b/acceptance/bundle/deploy/readplan/whl-upload/script
index c06707c5dd1..15b0c9aa6c3 100644
--- a/acceptance/bundle/deploy/readplan/whl-upload/script
+++ b/acceptance/bundle/deploy/readplan/whl-upload/script
@@ -5,9 +5,8 @@
 
 title "bundle deploy uploads the wheel"
 trace $CLI bundle deploy
-# An import-file request uploaded the wheel to its .../artifacts/.internal/ workspace path.
-# raw_body is the wheel's binary payload; drop it to keep the golden readable.
-trace print_requests.py //artifacts/.internal --del-field raw_body
+# The wheel was uploaded to its .../artifacts/.internal/ workspace path.
+trace print_workspace_imports | grep artifacts/.internal
 
 trace $CLI bundle destroy --auto-approve
 # Discard destroy's requests so the saved-plan deploy below starts from a clean recording.
@@ -19,9 +18,9 @@ title "bundle deploy --plan also uploads the wheel"
 $CLI bundle plan -o json > tmp.plan.json
 $CLI bundle plan -o json | nostamp > out.plan.json
 trace $CLI bundle deploy --plan tmp.plan.json
-# The same import-file request uploads the wheel to the .../artifacts/.internal/ path the
-# job task points at, matching the plain `bundle deploy` above.
-trace print_requests.py //artifacts/.internal --del-field raw_body
+# The wheel is uploaded to the same .../artifacts/.internal/ path the job task points at,
+# matching the plain `bundle deploy` above.
+trace print_workspace_imports | grep artifacts/.internal
 
 trace $CLI bundle destroy --auto-approve
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/deployment/bind/pipelines/recreate/output.txt b/acceptance/bundle/deployment/bind/pipelines/recreate/output.txt
index d641b59fc93..f114763c887 100644
--- a/acceptance/bundle/deployment/bind/pipelines/recreate/output.txt
+++ b/acceptance/bundle/deployment/bind/pipelines/recreate/output.txt
@@ -1,5 +1,5 @@
 
->>> print_requests.py ^//import-file/ ^//workspace/
+>>> print_requests.py ^//workspace/
 
 >>> [CLI] bundle summary -o json
 
@@ -34,4 +34,4 @@ Recreated pipelines.foo
 Files: 0 uploaded, 0 deleted
 Resources: 1 created, 0 changed, 1 deleted, 0 unchanged
 
->>> print_requests.py ^//import-file/ ^//workspace/ ^//telemetry-ext
+>>> print_requests.py ^//workspace/ ^//telemetry-ext
diff --git a/acceptance/bundle/deployment/bind/pipelines/recreate/script b/acceptance/bundle/deployment/bind/pipelines/recreate/script
index 9fd964fee14..8d02246da3b 100644
--- a/acceptance/bundle/deployment/bind/pipelines/recreate/script
+++ b/acceptance/bundle/deployment/bind/pipelines/recreate/script
@@ -6,11 +6,11 @@ add_repl $NEW_PIPELINE_ID NEW_PIPELINE_ID
 
 rm -f "$OUT_REQUESTS"
 trace musterr $CLI bundle deployment bind foo $NEW_PIPELINE_ID &> out.bind-fail.txt
-print_requests.py '^//import-file/' '^//workspace/'
+print_requests.py '^//workspace/'
 
 rm -f "$OUT_REQUESTS"
 trace $CLI bundle deployment bind foo $NEW_PIPELINE_ID --auto-approve &> out.bind-success.txt
-trace print_requests.py '^//import-file/' '^//workspace/'
+trace print_requests.py '^//workspace/'
 
 trace $CLI bundle summary -o json | jq .resources > out.summary.json
 trace $CLI bundle plan
@@ -19,4 +19,4 @@ trace musterr $CLI bundle deploy
 
 rm -f "$OUT_REQUESTS"
 trace $CLI bundle deploy --auto-approve
-trace print_requests.py '^//import-file/' '^//workspace/' '^//telemetry-ext' > out.deploy.requests.json
+trace print_requests.py '^//workspace/' '^//telemetry-ext' > out.deploy.requests.json
diff --git a/acceptance/bundle/deployment/bind/pipelines/update/output.txt b/acceptance/bundle/deployment/bind/pipelines/update/output.txt
index 5e1a9257fc1..732d4b8795c 100644
--- a/acceptance/bundle/deployment/bind/pipelines/update/output.txt
+++ b/acceptance/bundle/deployment/bind/pipelines/update/output.txt
@@ -19,4 +19,4 @@ Updated pipelines.foo
 Files: 6 uploaded, 0 deleted
 Resources: 0 created, 1 changed, 0 deleted, 0 unchanged
 
->>> print_requests.py ^//import-file/ ^//workspace/delete ^//telemetry-ext
+>>> print_requests.py ^//workspace/import ^//workspace/delete ^//telemetry-ext
diff --git a/acceptance/bundle/deployment/bind/pipelines/update/script b/acceptance/bundle/deployment/bind/pipelines/update/script
index 68ed3eca1f2..36c80f00f5d 100644
--- a/acceptance/bundle/deployment/bind/pipelines/update/script
+++ b/acceptance/bundle/deployment/bind/pipelines/update/script
@@ -3,15 +3,15 @@ add_repl $NEW_PIPELINE_ID NEW_PIPELINE_ID
 
 rm -f "$OUT_REQUESTS"
 trace musterr $CLI bundle deployment bind foo $NEW_PIPELINE_ID &> out.bind-fail.txt
-print_requests.py '^//import-file/' '^//workspace/delete'
+print_requests.py '^//workspace/import' '^//workspace/delete'
 
 rm -f "$OUT_REQUESTS"
 trace $CLI bundle deployment bind foo $NEW_PIPELINE_ID --auto-approve &> out.bind-success.txt
-print_requests.py '^//import-file/' '^//workspace/delete'
+print_requests.py '^//workspace/import' '^//workspace/delete'
 
 trace $CLI bundle summary -o json > out.summary.json
 trace $CLI bundle plan
 
 rm -f "$OUT_REQUESTS"
 trace $CLI bundle deploy --auto-approve
-trace print_requests.py '^//import-file/' '^//workspace/delete' '^//telemetry-ext' > out.deploy.requests.json
+trace print_requests.py '^//workspace/import' '^//workspace/delete' '^//telemetry-ext' > out.deploy.requests.json
diff --git a/acceptance/bundle/destroy/force-lock-node-limit/script b/acceptance/bundle/destroy/force-lock-node-limit/script
index c7fffbc16a2..616b626f2ef 100644
--- a/acceptance/bundle/destroy/force-lock-node-limit/script
+++ b/acceptance/bundle/destroy/force-lock-node-limit/script
@@ -7,9 +7,9 @@ title "Deploy (creates the job and the deployment)"
 trace $CLI bundle deploy
 
 title "destroy without --force-lock (lock write hits the node limit: aborts)"
-fault.py "POST /api/2.0/workspace-files/import-file/*" 403 0 1 MAX_CHILD_NODE_SIZE_EXCEEDED
+fault.py --body-contains "state/deploy.lock" "POST /api/2.0/workspace/import" 403 0 1 MAX_CHILD_NODE_SIZE_EXCEEDED
 trace errcode $CLI bundle destroy --auto-approve
 
 title "destroy with --force-lock (tolerates the node limit: proceeds and completes)"
-fault.py "POST /api/2.0/workspace-files/import-file/*" 403 0 1 MAX_CHILD_NODE_SIZE_EXCEEDED
+fault.py --body-contains "state/deploy.lock" "POST /api/2.0/workspace/import" 403 0 1 MAX_CHILD_NODE_SIZE_EXCEEDED
 trace $CLI bundle destroy --force-lock --auto-approve
diff --git a/acceptance/bundle/libraries/outside_of_bundle_root/output.txt b/acceptance/bundle/libraries/outside_of_bundle_root/output.txt
index 43e860f5d8e..976a2f7e3e6 100644
--- a/acceptance/bundle/libraries/outside_of_bundle_root/output.txt
+++ b/acceptance/bundle/libraries/outside_of_bundle_root/output.txt
@@ -54,8 +54,12 @@ Resources: 2 created, 0 changed, 0 deleted, 0 unchanged
 >>> cat [OUTPUT_DIR]/out.requests.txt
 {
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/outside_of_bundle_root/default/artifacts/.internal/test.whl",
-  "q": {
-    "overwrite": "true"
+  "path": "/api/2.0/workspace/import",
+  "body": {
+    "multipart_form": {
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/outside_of_bundle_root/default/artifacts/.internal/test.whl"
+    }
   }
 }
diff --git a/acceptance/bundle/libraries/outside_of_bundle_root/script b/acceptance/bundle/libraries/outside_of_bundle_root/script
index df54672eee7..7c4616890cc 100644
--- a/acceptance/bundle/libraries/outside_of_bundle_root/script
+++ b/acceptance/bundle/libraries/outside_of_bundle_root/script
@@ -11,6 +11,6 @@ title "Check that the job libraries are uploaded and the path is correct in the
 trace cat "$OUT_REQUESTS" | jq 'select(.path == "/api/2.2/jobs/create")' | jq '.body.tasks[0].libraries'
 trace cat "$OUT_REQUESTS" | jq 'select(.path == "/api/2.2/jobs/create")' | jq '.body.environments[0].spec.dependencies'
 trace cat "$OUT_REQUESTS" | jq 'select(.path == "/api/2.0/pipelines" and .method == "POST")' | jq '.body.environment.dependencies'
-trace cat "$OUT_REQUESTS" | jq 'select(.path | test("/api/2.0/workspace-files/import-file/Workspace/Users/.*/.bundle/outside_of_bundle_root/default/artifacts/.internal/test.whl"))'
+trace cat "$OUT_REQUESTS" | jq 'select(.path == "/api/2.0/workspace/import" and (.body.multipart_form.path // "" | test("/Workspace/Users/.*/.bundle/outside_of_bundle_root/default/artifacts/.internal/test.whl")))' | jq 'del(.body.multipart_form.content)'
 
 rm "$OUT_REQUESTS"
diff --git a/acceptance/bundle/migrate/auto/empty-tfstate/output.txt b/acceptance/bundle/migrate/auto/empty-tfstate/output.txt
index 54447ea8ecc..2569d95ccfb 100644
--- a/acceptance/bundle/migrate/auto/empty-tfstate/output.txt
+++ b/acceptance/bundle/migrate/auto/empty-tfstate/output.txt
@@ -20,16 +20,16 @@ direct_migrated_via_config true
 
 === The remote had no terraform state, so nothing terraform-related is backed up remotely
 
->>> print_requests.py //workspace-files/import-file //workspace/delete --sort
-"POST /api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/databricks.yml"
-"POST /api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
-"POST /api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
-"POST /api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json"
-"POST /api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json"
-"POST /api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/resources.json"
-"POST /api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/resources.json"
+>>> print_requests.py //workspace/import //workspace/delete --sort
 "POST /api/2.0/workspace/delete"
 "POST /api/2.0/workspace/delete"
+"POST /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/databricks.yml"
+"POST /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
+"POST /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
+"POST /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json"
+"POST /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json"
+"POST /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/resources.json"
+"POST /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/resources.json"
 
 === debug states confirms no terraform.tfstate anywhere; only the local .backup remains
 
diff --git a/acceptance/bundle/migrate/auto/empty-tfstate/script b/acceptance/bundle/migrate/auto/empty-tfstate/script
index 225092954a3..c0df01e54ec 100644
--- a/acceptance/bundle/migrate/auto/empty-tfstate/script
+++ b/acceptance/bundle/migrate/auto/empty-tfstate/script
@@ -19,7 +19,7 @@ title "Migration is recorded in telemetry as via-config\n"
 trace print_migration_telemetry
 
 title "The remote had no terraform state, so nothing terraform-related is backed up remotely\n"
-trace print_requests.py //workspace-files/import-file //workspace/delete --sort | jq '.method + " " + .path' | contains.py '!terraform.tfstate'
+trace print_requests.py //workspace/import //workspace/delete --sort | jq '.method + " " + (.body.multipart_form.path // .path)' | contains.py '!terraform.tfstate'
 
 title "debug states confirms no terraform.tfstate anywhere; only the local .backup remains\n"
 trace $CLI bundle debug states --force-pull
diff --git a/acceptance/bundle/migrate/auto/push-failure/output.txt b/acceptance/bundle/migrate/auto/push-failure/output.txt
index 6e9a1c61b78..bd638d6e829 100644
--- a/acceptance/bundle/migrate/auto/push-failure/output.txt
+++ b/acceptance/bundle/migrate/auto/push-failure/output.txt
@@ -8,7 +8,7 @@ Notice: migrating your bundle to direct deployment engine (https://github.com/da
 Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files...
 Error: access denied: /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/resources.json (403 INJECTED)
 
-Endpoint: POST [DATABRICKS_URL]/api/2.0/workspace-files/import-file/Workspace%2FUsers%2F[USERNAME]%2F.bundle%2Ftest-bundle%2Fdefault%2Fstate%2Fresources.json?overwrite=true
+Endpoint: POST [DATABRICKS_URL]/api/2.0/workspace/import
 HTTP Status: 403 Forbidden
 API error_code: INJECTED
 API message: Fault injected by test.
diff --git a/acceptance/bundle/migrate/auto/push-failure/script b/acceptance/bundle/migrate/auto/push-failure/script
index da3ffaad3d9..4231617175e 100644
--- a/acceptance/bundle/migrate/auto/push-failure/script
+++ b/acceptance/bundle/migrate/auto/push-failure/script
@@ -10,7 +10,7 @@ title "Opt in via env var; inject 403 on the resources.json push so the deploy f
 # push fails the deploy - unlike a declined deploy, the migration is not discarded, so the
 # local direct state remains and a retry finishes the push. (A push failure is a hard error on
 # any direct deploy, not just a migrating one.)
-fault.py "POST /api/2.0/workspace-files/import-file/Workspace/Users/$CURRENT_USER_NAME/.bundle/test-bundle/default/state/resources.json" 403 0 1
+fault.py --body-contains "Users/$CURRENT_USER_NAME/.bundle/test-bundle/default/state/resources.json" "POST /api/2.0/workspace/import" 403 0 1
 trace DATABRICKS_BUNDLE_ENGINE=direct errcode $CLI bundle deploy
 trace print_migration_telemetry
 rm -f "$OUT_REQUESTS"
diff --git a/acceptance/bundle/resource_deps/remote_app_url/output.txt b/acceptance/bundle/resource_deps/remote_app_url/output.txt
index 23808c5a896..503055861e5 100644
--- a/acceptance/bundle/resource_deps/remote_app_url/output.txt
+++ b/acceptance/bundle/resource_deps/remote_app_url/output.txt
@@ -18,7 +18,7 @@ create pipelines.mypipeline
 
 Plan: 2 to add, 0 to change, 0 to delete, 0 unchanged
 
->>> print_requests.py --nostamp ^//import-file/ ^//api/2.0/bundle
+>>> print_requests.py --nostamp ^//workspace/import ^//api/2.0/bundle
 {
   "method": "POST",
   "path": "/api/2.0/workspace/mkdirs",
@@ -34,7 +34,7 @@ Created pipelines.mypipeline
 Files: 0 uploaded, 0 deleted
 Resources: 2 created, 0 changed, 0 deleted, 0 unchanged
 
->>> print_requests.py --nostamp ^//import-file/ ^//api/2.0/bundle
+>>> print_requests.py --nostamp ^//workspace/import ^//api/2.0/bundle
 {
   "method": "POST",
   "path": "/api/2.0/workspace/mkdirs",
@@ -102,7 +102,7 @@ All files and directories at the following location will be deleted: /Workspace/
 
 Destroy: 2 deleted
 
->>> print_requests.py --nostamp --sort ^//import-file/ ^//api/2.0/bundle
+>>> print_requests.py --nostamp --sort ^//workspace/import ^//api/2.0/bundle
 {
   "method": "DELETE",
   "path": "/api/2.0/apps/myapp"
diff --git a/acceptance/bundle/resource_deps/remote_app_url/script b/acceptance/bundle/resource_deps/remote_app_url/script
index 6d1e4fd5839..ccd83d2f06d 100644
--- a/acceptance/bundle/resource_deps/remote_app_url/script
+++ b/acceptance/bundle/resource_deps/remote_app_url/script
@@ -1,9 +1,9 @@
 trace $CLI bundle validate
 trace $CLI bundle plan
-trace print_requests.py --nostamp '^//import-file/' '^//api/2.0/bundle'
+trace print_requests.py --nostamp '^//workspace/import' '^//api/2.0/bundle'
 
 trace $CLI bundle deploy
-trace print_requests.py --nostamp '^//import-file/' '^//api/2.0/bundle'
+trace print_requests.py --nostamp '^//workspace/import' '^//api/2.0/bundle'
 
 trace $CLI bundle destroy --auto-approve
-trace print_requests.py --nostamp --sort '^//import-file/' '^//api/2.0/bundle'
+trace print_requests.py --nostamp --sort '^//workspace/import' '^//api/2.0/bundle'
diff --git a/acceptance/bundle/resources/quality_monitors/change_assets_dir/output.txt b/acceptance/bundle/resources/quality_monitors/change_assets_dir/output.txt
index b53609dd402..9795d322b3e 100644
--- a/acceptance/bundle/resources/quality_monitors/change_assets_dir/output.txt
+++ b/acceptance/bundle/resources/quality_monitors/change_assets_dir/output.txt
@@ -23,7 +23,7 @@ Resources: 1 created, 0 changed, 0 deleted, 0 unchanged
 >>> [CLI] bundle plan
 Plan: 0 to add, 0 to change, 0 to delete, 1 unchanged
 
->>> print_requests.py ^//api/2.0/bundle ^//import-file/ ^//workspace/ ^//telemetry-ext
+>>> print_requests.py ^//api/2.0/bundle ^//workspace/ ^//telemetry-ext
 
 >>> [CLI] bundle destroy --auto-approve
 The following resources will be deleted:
diff --git a/acceptance/bundle/resources/quality_monitors/change_assets_dir/script b/acceptance/bundle/resources/quality_monitors/change_assets_dir/script
index 5ea603ee6fe..70fe4992c16 100644
--- a/acceptance/bundle/resources/quality_monitors/change_assets_dir/script
+++ b/acceptance/bundle/resources/quality_monitors/change_assets_dir/script
@@ -31,5 +31,5 @@ nostamp < .databricks/tmp.plan.json > out.plan.json
 
 rm "$OUT_REQUESTS"
 trace errcode $CLI bundle deploy &> out.deploy.txt
-trace print_requests.py '^//api/2.0/bundle' '^//import-file/' '^//workspace/' '^//telemetry-ext' > out.deploy.requests.json
+trace print_requests.py '^//api/2.0/bundle' '^//workspace/' '^//telemetry-ext' > out.deploy.requests.json
 trace errcode $CLI bundle plan &> out.plan_after_deploy.txt
diff --git a/acceptance/bundle/resources/quality_monitors/change_output_schema_name/output.txt b/acceptance/bundle/resources/quality_monitors/change_output_schema_name/output.txt
index e82dc779ba2..a23a2445c8b 100644
--- a/acceptance/bundle/resources/quality_monitors/change_output_schema_name/output.txt
+++ b/acceptance/bundle/resources/quality_monitors/change_output_schema_name/output.txt
@@ -36,7 +36,7 @@ Updated quality_monitors.monitor1
 Files: 2 uploaded, 0 deleted
 Resources: 0 created, 1 changed, 0 deleted, 0 unchanged
 
->>> print_requests.py ^//api/2.0/bundle ^//import-file/ ^//workspace/ ^//telemetry-ext
+>>> print_requests.py ^//api/2.0/bundle ^//workspace/ ^//telemetry-ext
 
 >>> [CLI] bundle plan
 Plan: 0 to add, 0 to change, 0 to delete, 1 unchanged
diff --git a/acceptance/bundle/resources/quality_monitors/change_output_schema_name/script b/acceptance/bundle/resources/quality_monitors/change_output_schema_name/script
index fbd62ade8df..a4104e4d387 100644
--- a/acceptance/bundle/resources/quality_monitors/change_output_schema_name/script
+++ b/acceptance/bundle/resources/quality_monitors/change_output_schema_name/script
@@ -27,6 +27,6 @@ trace $CLI bundle plan -o json | nostamp > out.plan.json
 rm "$OUT_REQUESTS"
 trace $CLI bundle deploy
 # dashboard_id is output only field that terraform adds
-trace print_requests.py '^//api/2.0/bundle' '^//import-file/' '^//workspace/' '^//telemetry-ext' | grep -v '"dashboard_id":' > out.deploy.requests.json
+trace print_requests.py '^//api/2.0/bundle' '^//workspace/' '^//telemetry-ext' | grep -v '"dashboard_id":' > out.deploy.requests.json
 
 trace $CLI bundle plan | contains.py "1 unchanged"
diff --git a/acceptance/bundle/resources/quality_monitors/change_table_name/output.txt b/acceptance/bundle/resources/quality_monitors/change_table_name/output.txt
index 77656aa1913..beba3487430 100644
--- a/acceptance/bundle/resources/quality_monitors/change_table_name/output.txt
+++ b/acceptance/bundle/resources/quality_monitors/change_table_name/output.txt
@@ -23,7 +23,7 @@ Resources: 1 created, 0 changed, 0 deleted, 0 unchanged
 >>> [CLI] bundle plan
 Plan: 0 to add, 0 to change, 0 to delete, 1 unchanged
 
->>> print_requests.py ^//api/2.0/bundle ^//import-file/ ^//workspace/ ^//telemetry-ext
+>>> print_requests.py ^//api/2.0/bundle ^//workspace/ ^//telemetry-ext
 
 >>> [CLI] bundle destroy --auto-approve
 The following resources will be deleted:
diff --git a/acceptance/bundle/resources/quality_monitors/change_table_name/script b/acceptance/bundle/resources/quality_monitors/change_table_name/script
index ca49568b38a..a17d8b114d4 100644
--- a/acceptance/bundle/resources/quality_monitors/change_table_name/script
+++ b/acceptance/bundle/resources/quality_monitors/change_table_name/script
@@ -31,7 +31,7 @@ nostamp < .databricks/tmp.plan.json > out.plan.json
 
 rm "$OUT_REQUESTS"
 trace errcode $CLI bundle deploy &> out.deploy.txt
-trace print_requests.py '^//api/2.0/bundle' '^//import-file/' '^//workspace/' '^//telemetry-ext' > out.deploy.requests.json
+trace print_requests.py '^//api/2.0/bundle' '^//workspace/' '^//telemetry-ext' > out.deploy.requests.json
 trace errcode $CLI bundle plan &> out.plan_after_deploy.txt
 
 trace errcode $CLI quality-monitors get ${TABLE_NAME}_2 2> /dev/null > out.get.json
diff --git a/acceptance/bundle/resources/quality_monitors/create/output.txt b/acceptance/bundle/resources/quality_monitors/create/output.txt
index fbe444e1eb7..5d1b3497525 100644
--- a/acceptance/bundle/resources/quality_monitors/create/output.txt
+++ b/acceptance/bundle/resources/quality_monitors/create/output.txt
@@ -16,7 +16,7 @@ Table main.qm_test_[UNIQUE_NAME].test_table is now visible (catalog_name=main)
 
 >>> [CLI] bundle plan -o json
 
->>> print_requests.py ^//api/2.0/bundle ^//import-file/ ^//workspace/ ^//telemetry-ext
+>>> print_requests.py ^//api/2.0/bundle ^//workspace/ ^//telemetry-ext
 
 >>> [CLI] bundle plan -o json
 
diff --git a/acceptance/bundle/resources/quality_monitors/create/script b/acceptance/bundle/resources/quality_monitors/create/script
index b45b8226f4e..1a3a60b1381 100644
--- a/acceptance/bundle/resources/quality_monitors/create/script
+++ b/acceptance/bundle/resources/quality_monitors/create/script
@@ -21,7 +21,7 @@ trace $CLI bundle plan -o json | nostamp > out.plan_create.json
 
 rm "$OUT_REQUESTS"
 trace $CLI bundle deploy &> out.deploy.txt
-trace print_requests.py '^//api/2.0/bundle' '^//import-file/' '^//workspace/' '^//telemetry-ext' > out.deploy.requests.json
+trace print_requests.py '^//api/2.0/bundle' '^//workspace/' '^//telemetry-ext' > out.deploy.requests.json
 
 # store state to ensure we have table_name there
 print_state.py | grep name > out.state.txt
diff --git a/acceptance/bundle/resources/secret_scopes/delete_scope/out.deploy.requests.txt b/acceptance/bundle/resources/secret_scopes/delete_scope/out.deploy.requests.txt
index e21f54fcf1f..1943374afeb 100644
--- a/acceptance/bundle/resources/secret_scopes/delete_scope/out.deploy.requests.txt
+++ b/acceptance/bundle/resources/secret_scopes/delete_scope/out.deploy.requests.txt
@@ -1,5 +1,5 @@
 
->>> print_requests.py ^//api/2.0/bundle ^//import-file/ ^//workspace/ ^//telemetry-ext
+>>> print_requests.py ^//api/2.0/bundle ^//workspace/ ^//telemetry-ext
 {
   "method": "POST",
   "path": "/api/2.0/secrets/scopes/delete",
diff --git a/acceptance/bundle/resources/secret_scopes/delete_scope/script b/acceptance/bundle/resources/secret_scopes/delete_scope/script
index 6cd30fffdae..8d04d13a33f 100755
--- a/acceptance/bundle/resources/secret_scopes/delete_scope/script
+++ b/acceptance/bundle/resources/secret_scopes/delete_scope/script
@@ -15,4 +15,4 @@ trace $CLI bundle plan &> out.plan.txt
 rm "$OUT_REQUESTS"
 
 trace $CLI bundle deploy -qq
-trace print_requests.py '^//api/2.0/bundle' '^//import-file/' '^//workspace/' '^//telemetry-ext' &> out.deploy.requests.txt
+trace print_requests.py '^//api/2.0/bundle' '^//workspace/' '^//telemetry-ext' &> out.deploy.requests.txt
diff --git a/acceptance/bundle/sync-upload-edge-cases/databricks.yml b/acceptance/bundle/sync-upload-edge-cases/databricks.yml
new file mode 100644
index 00000000000..2261ff177c7
--- /dev/null
+++ b/acceptance/bundle/sync-upload-edge-cases/databricks.yml
@@ -0,0 +1,2 @@
+bundle:
+  name: upload-edge-cases
diff --git a/acceptance/bundle/sync-upload-edge-cases/out.test.toml b/acceptance/bundle/sync-upload-edge-cases/out.test.toml
new file mode 100644
index 00000000000..59b56a2037c
--- /dev/null
+++ b/acceptance/bundle/sync-upload-edge-cases/out.test.toml
@@ -0,0 +1,3 @@
+Cloud = false
+EnvMatrix.DATABRICKS_BUNDLE_ENGINE = ["direct"]
+EnvMatrix.DMS = ["", "true"]
diff --git a/acceptance/bundle/sync-upload-edge-cases/output.txt b/acceptance/bundle/sync-upload-edge-cases/output.txt
new file mode 100644
index 00000000000..8ce0c31d5dc
--- /dev/null
+++ b/acceptance/bundle/sync-upload-edge-cases/output.txt
@@ -0,0 +1,136 @@
+
+>>> [CLI] bundle sync --output text
+Action: PUT: .gitignore, dashboard.lvdash.json, databricks.yml, empty.txt, héllo.txt, large.bin, plain-script.py, pyNb.py, scalaNb.scala, sqlNb.sql, with spaces.txt
+Initial Sync Complete
+Uploaded .gitignore
+Uploaded dashboard.lvdash.json
+Uploaded databricks.yml
+Uploaded empty.txt
+Uploaded héllo.txt
+Uploaded large.bin
+Uploaded plain-script.py
+Uploaded pyNb.py
+Uploaded scalaNb.scala
+Uploaded sqlNb.sql
+Uploaded with spaces.txt
+
+=== workspace state after sync — assert object_type and language for each upload
+>>> MSYS_NO_PATHCONV=1 [CLI] workspace list -o json /Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files
+{
+  "name": ".gitignore",
+  "object_type": "FILE",
+  "language": null
+}
+{
+  "name": "dashboard.lvdash.json",
+  "object_type": "FILE",
+  "language": null
+}
+{
+  "name": "databricks.yml",
+  "object_type": "FILE",
+  "language": null
+}
+{
+  "name": "empty.txt",
+  "object_type": "FILE",
+  "language": null
+}
+{
+  "name": "héllo.txt",
+  "object_type": "FILE",
+  "language": null
+}
+{
+  "name": "large.bin",
+  "object_type": "FILE",
+  "language": null
+}
+{
+  "name": "plain-script.py",
+  "object_type": "FILE",
+  "language": null
+}
+{
+  "name": "pyNb",
+  "object_type": "NOTEBOOK",
+  "language": "PYTHON"
+}
+{
+  "name": "scalaNb",
+  "object_type": "NOTEBOOK",
+  "language": "SCALA"
+}
+{
+  "name": "sqlNb",
+  "object_type": "NOTEBOOK",
+  "language": "SQL"
+}
+{
+  "name": "with spaces.txt",
+  "object_type": "FILE",
+  "language": null
+}
+
+=== uploaded paths from each multipart POST /workspace/import (sorted)
+>>> print_workspace_imports
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/.gitignore
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/dashboard.lvdash.json
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/databricks.yml
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/empty.txt
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/héllo.txt
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/large.bin
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/plain-script.py
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/pyNb.py
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/scalaNb.scala
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/sqlNb.sql
+/Workspace/Users/[USERNAME]/.bundle/upload-edge-cases/default/files/with spaces.txt
+
+=== every upload set format=AUTO
+>>> jq -rs 
+  map(select(.path == "/api/2.0/workspace/import")) |
+  map(.body.multipart_form.format) | unique
+ [OUTPUT_DIR]/out.requests.txt
+[
+  "AUTO"
+]
+
+=== recorded content for the small text inputs
+>>> jq -rs 
+  map(select(.path == "/api/2.0/workspace/import")) |
+  map(select(.body.multipart_form.path | test("/(pyNb\\.py|sqlNb\\.sql|scalaNb\\.scala|plain-script\\.py|héllo\\.txt|with spaces\\.txt|empty\\.txt|dashboard\\.lvdash\\.json)$"))) |
+  map({path: (.body.multipart_form.path | sub(".*/"; "")), content: .body.multipart_form.content}) |
+  sort_by(.path) | .[]
+ [OUTPUT_DIR]/out.requests.txt
+{
+  "path": "dashboard.lvdash.json",
+  "content": "{\"datasets\":[],\"pages\":[]}\n"
+}
+{
+  "path": "empty.txt",
+  "content": ""
+}
+{
+  "path": "héllo.txt",
+  "content": "hello, naïve world\n"
+}
+{
+  "path": "plain-script.py",
+  "content": "print(\"plain script, no header\")\n"
+}
+{
+  "path": "pyNb.py",
+  "content": "# Databricks notebook source\nprint(\"hello\")\n"
+}
+{
+  "path": "scalaNb.scala",
+  "content": "// Databricks notebook source\nprintln(\"hello\")\n"
+}
+{
+  "path": "sqlNb.sql",
+  "content": "-- Databricks notebook source\nSELECT 1\n"
+}
+{
+  "path": "with spaces.txt",
+  "content": "hello, world\n"
+}
diff --git a/acceptance/bundle/sync-upload-edge-cases/script b/acceptance/bundle/sync-upload-edge-cases/script
new file mode 100644
index 00000000000..bfd3abcaa03
--- /dev/null
+++ b/acceptance/bundle/sync-upload-edge-cases/script
@@ -0,0 +1,92 @@
+# Confidence checks that /workspace/import is a drop-in for the legacy import-file:
+# verify the CLI's multipart upload pipeline handles the cases that differ between the
+# two endpoints — large content (>10 MB), empty content, varied extensions/object types,
+# and non-ASCII / spaced filenames in the multipart `path` field.
+
+# Exclude framework-generated and script-internal files from the sync. We only want the
+# inputs we explicitly generate below to show up in the recorded uploads.
+cat > .gitignore <<'EOF'
+script
+output.txt
+out.requests.txt
+repls.json
+test.toml
+.databricks
+EOF
+
+# 12 MiB binary file, over the 10 MB cap on the JSON-body variant's base64 `content`
+# field. The multipart variant this test exercises has no such cap. Generated
+# dynamically to keep the repo small.
+python3 -c "open('large.bin', 'wb').write(b'\\0' * (12 * 1024 * 1024))"
+
+# Empty file (multipart encodes an empty `content` part — distinct from JSON's empty string).
+touch empty.txt
+
+# Python notebook: auto-detected as NOTEBOOK by /workspace/import; testserver mirrors
+# this and stores the object at the path with .py stripped.
+cat > pyNb.py <<'EOF'
+# Databricks notebook source
+print("hello")
+EOF
+
+# SQL notebook: -- comment header, .sql extension, Language=SQL on the workspace side.
+cat > sqlNb.sql <<'EOF'
+-- Databricks notebook source
+SELECT 1
+EOF
+
+# Scala notebook: // comment header, .scala extension, Language=SCALA.
+cat > scalaNb.scala <<'EOF'
+// Databricks notebook source
+println("hello")
+EOF
+
+# Plain .py without the source header — should land as FILE, not NOTEBOOK,
+# even though the extension is .py.
+cat > plain-script.py <<'EOF'
+print("plain script, no header")
+EOF
+
+# Lakeview dashboard descriptor: the real /workspace/import assigns object_type=DASHBOARD
+# and preserves the .lvdash.json extension. The testserver doesn't emulate that and stores
+# it as a generic FILE — but the upload-side request shape (which is what this test asserts)
+# is identical.
+echo '{"datasets":[],"pages":[]}' > dashboard.lvdash.json
+
+# Non-ASCII filename. Multipart encodes filenames with RFC 5987 / quoted-string rules,
+# distinct from URL-encoding in the legacy import-file endpoint.
+echo "hello, naïve world" > "héllo.txt"
+
+# Filename with a space.
+echo "hello, world" > "with spaces.txt"
+
+trace $CLI bundle sync --output text 2>&1 | sort
+
+title "workspace state after sync — assert object_type and language for each upload"
+remote_files=$($CLI bundle summary -o json 2>/dev/null | jq -r .workspace.file_path)
+# MSYS_NO_PATHCONV stops Git Bash on Windows from rewriting the leading-slash
+# workspace path into a C:/Program Files/... filesystem path before it
+# reaches the CLI.
+trace MSYS_NO_PATHCONV=1 $CLI workspace list -o json "$remote_files" |
+  jq 'sort_by(.path) | .[] | {name: (.path | sub(".*/"; "")), object_type, language}'
+
+title "uploaded paths from each multipart POST /workspace/import (sorted)"
+trace print_workspace_imports | sort
+
+title "every upload set format=AUTO"
+trace jq -rs '
+  map(select(.path == "/api/2.0/workspace/import")) |
+  map(.body.multipart_form.format) | unique
+' "$OUT_REQUESTS"
+
+title "recorded content for the small text inputs"
+trace jq -rs '
+  map(select(.path == "/api/2.0/workspace/import")) |
+  map(select(.body.multipart_form.path | test("/(pyNb\\.py|sqlNb\\.sql|scalaNb\\.scala|plain-script\\.py|héllo\\.txt|with spaces\\.txt|empty\\.txt|dashboard\\.lvdash\\.json)$"))) |
+  map({path: (.body.multipart_form.path | sub(".*/"; "")), content: .body.multipart_form.content}) |
+  sort_by(.path) | .[]
+' "$OUT_REQUESTS"
+
+# Drop the recorded requests; their workspace-prefixed paths are noisy and the
+# assertions above already pin the relevant fields.
+rm "$OUT_REQUESTS" .gitignore
diff --git a/acceptance/bundle/sync-upload-edge-cases/test.toml b/acceptance/bundle/sync-upload-edge-cases/test.toml
new file mode 100644
index 00000000000..8bfde26201e
--- /dev/null
+++ b/acceptance/bundle/sync-upload-edge-cases/test.toml
@@ -0,0 +1,18 @@
+RecordRequests = true
+
+# All sync uploads go through the same /workspace/import multipart code path; running
+# both engine variants is unnecessary here.
+EnvMatrix.DATABRICKS_BUNDLE_ENGINE = ["direct"]
+
+Ignore = [
+  "large.bin",
+  "empty.txt",
+  "pyNb.py",
+  "sqlNb.sql",
+  "scalaNb.scala",
+  "plain-script.py",
+  "dashboard.lvdash.json",
+  "héllo.txt",
+  "with spaces.txt",
+  ".databricks",
+]
diff --git a/acceptance/bundle/telemetry/deploy-failed-engine-unknown/output.txt b/acceptance/bundle/telemetry/deploy-failed-engine-unknown/output.txt
index 17eb89280ce..df5252aa3d7 100644
--- a/acceptance/bundle/telemetry/deploy-failed-engine-unknown/output.txt
+++ b/acceptance/bundle/telemetry/deploy-failed-engine-unknown/output.txt
@@ -1,9 +1,9 @@
 
 >>> [CLI] bundle deploy
-Error: Failed to acquire deployment lock: Internal error
-Error: Internal error (500 INTERNAL_ERROR)
+Error: Failed to acquire deployment lock: failed to upload /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock: Internal error
+Error: failed to upload /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock: Internal error (500 INTERNAL_ERROR)
 
-Endpoint: POST [DATABRICKS_URL]/api/2.0/workspace-files/import-file/Workspace%2FUsers%2F[USERNAME]%2F.bundle%2Ftest-bundle%2Fdefault%2Fstate%2Fdeploy.lock?overwrite=false
+Endpoint: POST [DATABRICKS_URL]/api/2.0/workspace/import
 HTTP Status: 500 Internal Server Error
 API error_code: INTERNAL_ERROR
 API message: Internal error
diff --git a/acceptance/bundle/telemetry/deploy-failed-engine-unknown/test.toml b/acceptance/bundle/telemetry/deploy-failed-engine-unknown/test.toml
index 86d366ba8c2..1e685cca603 100644
--- a/acceptance/bundle/telemetry/deploy-failed-engine-unknown/test.toml
+++ b/acceptance/bundle/telemetry/deploy-failed-engine-unknown/test.toml
@@ -12,6 +12,6 @@
 Cloud = false
 
 [[Server]]
-Pattern = "POST /api/2.0/workspace-files/import-file/{path...}"
+Pattern = "POST /api/2.0/workspace/import"
 Response.StatusCode = 500
 Response.Body = '''{"error_code": "INTERNAL_ERROR", "message": "Internal error"}'''
diff --git a/acceptance/bundle/templates/default-python/classic/script b/acceptance/bundle/templates/default-python/classic/script
index 3029c012d05..2f91efecbe1 100644
--- a/acceptance/bundle/templates/default-python/classic/script
+++ b/acceptance/bundle/templates/default-python/classic/script
@@ -13,13 +13,13 @@ $CLI bundle plan -o json -t prod | nostamp > ../../out.plan_prod.json
 rm "$OUT_REQUESTS"
 # With --plan variant we don't build artifacts, so we can filter out relevant log lines
 $CLI bundle deploy -t dev $(readplanarg ../../out.plan_dev.json) 2>&1 | grep -vE '^Building python_artifact|^Uploading .databricks'
-print_requests.py --sort '^//import-file/' '^//telemetry-ext' > ../../out.requests.dev.txt
+print_requests.py --sort '^//workspace/import' '^//telemetry-ext' > ../../out.requests.dev.txt
 read_id.py -t dev sample_job > /dev/null
 trace $CLI bundle plan -t dev  # check if if there is drift
 trace $CLI bundle plan -t dev -o json | nostamp > ../../out.plan_after_deploy_dev.json
 
 $CLI bundle deploy -t prod $(readplanarg ../../out.plan_prod.json) 2>&1 | grep -vE '^Building python_artifact|^Uploading dist'
-print_requests.py --sort '^//import-file/' '^//telemetry-ext' > ../../out.requests.prod.txt
+print_requests.py --sort '^//workspace/import' '^//telemetry-ext' > ../../out.requests.prod.txt
 read_id.py -t prod sample_job > /dev/null
 # Extracted with python, not jq: the id exceeds 2^53 and jq 1.6 rounds it.
 root_dir_id=$(MSYS_NO_PATHCONV=1 $CLI workspace get-status "/Workspace/Users/${CURRENT_USER_NAME}/.bundle/my_default_python/prod" -o json | python3 -c 'import sys, json; print(json.load(sys.stdin)["object_id"])')
diff --git a/acceptance/bundle/templates/default-python/serverless/script b/acceptance/bundle/templates/default-python/serverless/script
index 93e5048afec..a5d2a395976 100644
--- a/acceptance/bundle/templates/default-python/serverless/script
+++ b/acceptance/bundle/templates/default-python/serverless/script
@@ -13,13 +13,13 @@ $CLI bundle plan -o json -t prod | nostamp > ../../out.plan_prod.json
 rm "$OUT_REQUESTS"
 trace $CLI bundle deploy -t dev
 replace_ids.py -t dev
-print_requests.py --sort '^//import-file/' '^//telemetry-ext' > ../../out.requests.dev.txt
+print_requests.py --sort '^//workspace/import' '^//telemetry-ext' > ../../out.requests.dev.txt
 trace $CLI bundle plan -t dev  # check if if there is drift
 trace $CLI bundle plan -t dev -o json | nostamp > ../../out.plan_after_deploy_dev.json
 
 trace $CLI bundle deploy -t prod
 replace_ids.py -t prod
-print_requests.py --sort '^//import-file/' '^//telemetry-ext' > ../../out.requests.prod.txt
+print_requests.py --sort '^//workspace/import' '^//telemetry-ext' > ../../out.requests.prod.txt
 trace $CLI bundle plan -t prod  # check if there is drift
 trace $CLI bundle plan -t prod -o json | nostamp > ../../out.plan_after_deploy_prod.json
 
diff --git a/acceptance/bundle/upload/internal_server_error/output.txt b/acceptance/bundle/upload/internal_server_error/output.txt
index 5cde6aad650..794a0ed2072 100644
--- a/acceptance/bundle/upload/internal_server_error/output.txt
+++ b/acceptance/bundle/upload/internal_server_error/output.txt
@@ -1,8 +1,8 @@
 Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files...
-Error: Internal Server Error (500)
+Error: failed to upload /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/file_to_upload.txt: Fault injected by test. (500 INJECTED)
 
-Endpoint: POST [DATABRICKS_URL]/api/2.0/workspace-files/import-file/Workspace%2FUsers%2F[USERNAME]%2F.bundle%2Ftest-bundle%2Fdefault%2Ffiles%2Ffile_to_upload.txt?overwrite=true
+Endpoint: POST [DATABRICKS_URL]/api/2.0/workspace/import
 HTTP Status: 500 Internal Server Error
-API error_code: 
-API message: Internal Server Error
+API error_code: INJECTED
+API message: Fault injected by test.
 
diff --git a/acceptance/bundle/upload/internal_server_error/script b/acceptance/bundle/upload/internal_server_error/script
index c1a222958e1..78c57ef8a94 100644
--- a/acceptance/bundle/upload/internal_server_error/script
+++ b/acceptance/bundle/upload/internal_server_error/script
@@ -1 +1,2 @@
+fault.py --body-contains "Users/$CURRENT_USER_NAME/.bundle/test-bundle/default/files/file_to_upload.txt" "POST /api/2.0/workspace/import" 500 0 1000
 musterr $CLI bundle deploy
diff --git a/acceptance/bundle/upload/internal_server_error/test.toml b/acceptance/bundle/upload/internal_server_error/test.toml
deleted file mode 100644
index 8ff8501b6de..00000000000
--- a/acceptance/bundle/upload/internal_server_error/test.toml
+++ /dev/null
@@ -1,3 +0,0 @@
-[[Server]]
-Pattern = "POST /api/2.0/workspace-files/import-file/Workspace/Users/tester@databricks.com/.bundle/test-bundle/default/files/file_to_upload.txt"
-Response.StatusCode = 500
diff --git a/acceptance/bundle/upload/timeout/output.txt b/acceptance/bundle/upload/timeout/output.txt
index c314a247707..0c779d73dc2 100644
--- a/acceptance/bundle/upload/timeout/output.txt
+++ b/acceptance/bundle/upload/timeout/output.txt
@@ -1,3 +1,3 @@
-Uploading bundle files to /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files...
-Error: Post "[DATABRICKS_URL]/api/2.0/workspace-files/import-file/Workspace%2FUsers%2F[USERNAME]%2F.bundle%2Ftest-bundle%2Fdefault%2Ffiles%2Ffile_to_upload.txt?overwrite=true": request timed out after 5s of inactivity
+Error: Failed to acquire deployment lock: failed to upload /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock: Post "[DATABRICKS_URL]/api/2.0/workspace/import": request timed out after 5s of inactivity
+Error: failed to upload /Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock: Post "[DATABRICKS_URL]/api/2.0/workspace/import": request timed out after 5s of inactivity
 
diff --git a/acceptance/bundle/upload/timeout/test.toml b/acceptance/bundle/upload/timeout/test.toml
index d6564ef9659..f0abd08ecbc 100644
--- a/acceptance/bundle/upload/timeout/test.toml
+++ b/acceptance/bundle/upload/timeout/test.toml
@@ -3,5 +3,5 @@ Env.DATABRICKS_BUNDLE_HTTP_TIMEOUT_SECONDS = "5"
 [[Server]]
 # CLI aborts after a single attempt when the HTTP timeout fires.
 Delay = "30s"
-Pattern = "POST /api/2.0/workspace-files/import-file/Workspace/Users/tester@databricks.com/.bundle/test-bundle/default/files/file_to_upload.txt"
+Pattern = "POST /api/2.0/workspace/import"
 Response.StatusCode = 200
diff --git a/acceptance/bundle/user_agent/output.txt b/acceptance/bundle/user_agent/output.txt
index 947a3167408..d4faf40804a 100644
--- a/acceptance/bundle/user_agent/output.txt
+++ b/acceptance/bundle/user_agent/output.txt
@@ -8,14 +8,14 @@ OK  	deploy	/api/2.0/workspace/get-status	engine/direct
 OK  	deploy	/api/2.0/workspace/get-status	engine/direct
 OK  	deploy	/api/2.0/workspace/get-status	engine/direct
 OK  	deploy	/api/2.0/workspace/get-status	engine/direct
-OK  	deploy	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/empty.py	engine/direct
-OK  	deploy	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock	engine/direct
-OK  	deploy	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock	engine/direct
-OK  	deploy	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json	engine/direct
-OK  	deploy	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json	engine/direct
-OK  	deploy	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/resources.json	engine/direct
 OK  	deploy	/api/2.0/workspace/delete	engine/direct
 OK  	deploy	/api/2.0/workspace/delete	engine/direct
+OK  	deploy	/api/2.0/workspace/import	engine/direct
+OK  	deploy	/api/2.0/workspace/import	engine/direct
+OK  	deploy	/api/2.0/workspace/import	engine/direct
+OK  	deploy	/api/2.0/workspace/import	engine/direct
+OK  	deploy	/api/2.0/workspace/import	engine/direct
+OK  	deploy	/api/2.0/workspace/import	engine/direct
 OK  	deploy	/api/2.0/workspace/mkdirs	engine/direct
 OK  	deploy	/api/2.0/workspace/mkdirs	engine/direct
 OK  	deploy	/api/2.1/unity-catalog/schemas	engine/direct
@@ -30,9 +30,9 @@ OK  	destroy	/api/2.0/workspace/get-status	engine/direct
 OK  	destroy	/api/2.0/workspace/get-status	engine/direct
 OK  	destroy	/api/2.0/workspace/get-status	engine/direct
 OK  	destroy	/api/2.1/unity-catalog/schemas/mycatalog.myschema	engine/direct
-OK  	destroy	/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock	engine/direct
 OK  	destroy	/api/2.0/workspace/delete	engine/direct
 OK  	destroy	/api/2.0/workspace/delete	engine/direct
+OK  	destroy	/api/2.0/workspace/import	engine/direct
 MISS	destroy	/.well-known/databricks-config	'cli/[CLI_VERSION] databricks-sdk-go/[SDK_VERSION] go/[GO_VERSION] os/[OS]'
 MISS	plan	/api/2.0/preview/scim/v2/Me	'cli/[CLI_VERSION] databricks-sdk-go/[SDK_VERSION] go/[GO_VERSION] os/[OS] cmd/bundle_plan cmd-exec-id/[UUID] interactive/none auth/pat'
 MISS	plan	/api/2.0/workspace/get-status	'cli/[CLI_VERSION] databricks-sdk-go/[SDK_VERSION] go/[GO_VERSION] os/[OS] cmd/bundle_plan cmd-exec-id/[UUID] interactive/none auth/pat'
diff --git a/acceptance/bundle/user_agent/simple/out.requests.deploy.json b/acceptance/bundle/user_agent/simple/out.requests.deploy.json
index f0c60602386..6617ac3b1ac 100644
--- a/acceptance/bundle/user_agent/simple/out.requests.deploy.json
+++ b/acceptance/bundle/user_agent/simple/out.requests.deploy.json
@@ -130,9 +130,10 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/empty.py",
-  "q": {
-    "overwrite": "true"
+  "path": "/api/2.0/workspace/delete",
+  "body": {
+    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal",
+    "recursive": true
   }
 }
 {
@@ -142,15 +143,9 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock",
-  "q": {
-    "overwrite": "false"
-  },
+  "path": "/api/2.0/workspace/delete",
   "body": {
-    "ID": "[UUID]",
-    "AcquisitionTime": "[TIMESTAMP]",
-    "IsForced": false,
-    "User": "[USERNAME]"
+    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
   }
 }
 {
@@ -160,15 +155,14 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock",
-  "q": {
-    "overwrite": "false"
-  },
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "ID": "[UUID]",
-    "AcquisitionTime": "[TIMESTAMP]",
-    "IsForced": false,
-    "User": "[USERNAME]"
+    "multipart_form": {
+      "content": "",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/empty.py"
+    }
   }
 }
 {
@@ -178,22 +172,13 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json",
-  "q": {
-    "overwrite": "true"
-  },
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "version": 1,
-    "seq": 1,
-    "cli_version": "[CLI_VERSION]",
-    "timestamp": "[TIMESTAMP]",
-    "files": [
-      {
-        "local_path": "empty.py",
-        "is_notebook": false
-      }
-    ],
-    "id": "[UUID]"
+    "multipart_form": {
+      "content": "{\"ID\":\"[UUID]\",\"AcquisitionTime\":\"[TIMESTAMP]\",\"IsForced\":false,\"User\":\"[USERNAME]\"}",
+      "format": "AUTO",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
+    }
   }
 }
 {
@@ -203,29 +188,13 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json",
-  "q": {
-    "overwrite": "true"
-  },
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "version": 1,
-    "config": {
-      "bundle": {
-        "name": "test-bundle",
-        "target": "default",
-        "git": {
-          "bundle_root_path": "."
-        }
-      },
-      "workspace": {
-        "file_path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files"
-      },
-      "resources": {},
-      "presets": {
-        "source_linked_deployment": false
-      }
-    },
-    "extra": {}
+    "multipart_form": {
+      "content": "{\"ID\":\"[UUID]\",\"AcquisitionTime\":\"[TIMESTAMP]\",\"IsForced\":false,\"User\":\"[USERNAME]\"}",
+      "format": "AUTO",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
+    }
   }
 }
 {
@@ -235,23 +204,13 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/resources.json",
-  "q": {
-    "overwrite": "true"
-  },
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "state_version": 3,
-    "cli_version": "[CLI_VERSION]",
-    "lineage": "[UUID]",
-    "serial": 1,
-    "state": {
-      "resources.schemas.foo": {
-        "__id__": "mycatalog.myschema",
-        "state": {
-          "catalog_name": "mycatalog",
-          "name": "myschema"
-        }
-      }
+    "multipart_form": {
+      "content": "{\"version\":1,\"seq\":1,\"cli_version\":\"[CLI_VERSION]\",\"timestamp\":\"[TIMESTAMP]\",\"files\":[{\"local_path\":\"empty.py\",\"is_notebook\":false}],\"id\":\"[UUID]\"}",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deployment.json"
     }
   }
 }
@@ -262,10 +221,14 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace/delete",
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/artifacts/.internal",
-    "recursive": true
+    "multipart_form": {
+      "content": "{\n  \"version\": 1,\n  \"config\": {\n    \"bundle\": {\n      \"name\": \"test-bundle\",\n      \"target\": \"default\",\n      \"git\": {\n        \"bundle_root_path\": \".\"\n      }\n    },\n    \"workspace\": {\n      \"file_path\": \"/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files\"\n    },\n    \"resources\": {},\n    \"presets\": {\n      \"source_linked_deployment\": false\n    }\n  },\n  \"extra\": {}\n}",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/metadata.json"
+    }
   }
 }
 {
@@ -275,9 +238,14 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace/delete",
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
+    "multipart_form": {
+      "content": "{\n \"state_version\": 3,\n \"cli_version\": \"[CLI_VERSION]\",\n \"lineage\": \"[UUID]\",\n \"serial\": 1,\n \"state\": {\n  \"resources.schemas.foo\": {\n   \"__id__\": \"mycatalog.myschema\",\n   \"state\": {\n    \"catalog_name\": \"mycatalog\",\n    \"name\": \"myschema\"\n   }\n  }\n }\n}",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/resources.json"
+    }
   }
 }
 {
diff --git a/acceptance/bundle/user_agent/simple/out.requests.destroy.json b/acceptance/bundle/user_agent/simple/out.requests.destroy.json
index 43de64cf21f..49ae5e2cfc9 100644
--- a/acceptance/bundle/user_agent/simple/out.requests.destroy.json
+++ b/acceptance/bundle/user_agent/simple/out.requests.destroy.json
@@ -125,15 +125,9 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock",
-  "q": {
-    "overwrite": "false"
-  },
+  "path": "/api/2.0/workspace/delete",
   "body": {
-    "ID": "[UUID]",
-    "AcquisitionTime": "[TIMESTAMP]",
-    "IsForced": false,
-    "User": "[USERNAME]"
+    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle"
   }
 }
 {
@@ -145,7 +139,8 @@
   "method": "POST",
   "path": "/api/2.0/workspace/delete",
   "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle"
+    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default",
+    "recursive": true
   }
 }
 {
@@ -155,10 +150,13 @@
     ]
   },
   "method": "POST",
-  "path": "/api/2.0/workspace/delete",
+  "path": "/api/2.0/workspace/import",
   "body": {
-    "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default",
-    "recursive": true
+    "multipart_form": {
+      "content": "{\"ID\":\"[UUID]\",\"AcquisitionTime\":\"[TIMESTAMP]\",\"IsForced\":false,\"User\":\"[USERNAME]\"}",
+      "format": "AUTO",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/state/deploy.lock"
+    }
   }
 }
 {
diff --git a/acceptance/bundle/validate/sync_patterns/out.sync.txt b/acceptance/bundle/validate/sync_patterns/out.sync.txt
index ac5aba9ab29..fd939c9721b 100644
--- a/acceptance/bundle/validate/sync_patterns/out.sync.txt
+++ b/acceptance/bundle/validate/sync_patterns/out.sync.txt
@@ -1,7 +1,12 @@
 {
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/conf/dir/test.yml",
-  "q": {
-    "overwrite": "true"
+  "path": "/api/2.0/workspace/import",
+  "body": {
+    "multipart_form": {
+      "content": "",
+      "format": "AUTO",
+      "overwrite": "true",
+      "path": "/Workspace/Users/[USERNAME]/.bundle/test-bundle/default/files/conf/dir/test.yml"
+    }
   }
 }
diff --git a/acceptance/bundle/validate/sync_patterns/script b/acceptance/bundle/validate/sync_patterns/script
index d4cf7169b1b..f44ee310433 100644
--- a/acceptance/bundle/validate/sync_patterns/script
+++ b/acceptance/bundle/validate/sync_patterns/script
@@ -1,5 +1,5 @@
 trace $CLI bundle validate
 trace $CLI bundle validate -o json | jq '.sync'
 trace $CLI bundle deploy
-jq 'select(.path | test("dir/test.yml"))' "$OUT_REQUESTS"  > out.sync.txt
+jq 'select(.body.multipart_form.path | strings | test("dir/test.yml"))' "$OUT_REQUESTS"  > out.sync.txt
 rm "$OUT_REQUESTS"
diff --git a/acceptance/cmd/sync/dryrun-missing-remote/output.txt b/acceptance/cmd/sync/dryrun-missing-remote/output.txt
index 4848aae1c2d..b7453994b58 100644
--- a/acceptance/cmd/sync/dryrun-missing-remote/output.txt
+++ b/acceptance/cmd/sync/dryrun-missing-remote/output.txt
@@ -15,11 +15,11 @@ Uploaded hello.py
 >>> print_requests.py --sort //api/
 {
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Users/[USERNAME]/missing-dir-[UNIQUE_NAME]/.gitignore"
+  "path": "/api/2.0/workspace/import"
 }
 {
   "method": "POST",
-  "path": "/api/2.0/workspace-files/import-file/Users/[USERNAME]/missing-dir-[UNIQUE_NAME]/hello.py"
+  "path": "/api/2.0/workspace/import"
 }
 {
   "method": "POST",
diff --git a/acceptance/internal/prepare_server.go b/acceptance/internal/prepare_server.go
index 239a4a904a1..468aa02dc9e 100644
--- a/acceptance/internal/prepare_server.go
+++ b/acceptance/internal/prepare_server.go
@@ -1,8 +1,12 @@
 package internal
 
 import (
+	"bytes"
 	"encoding/json"
 	"fmt"
+	"io"
+	"mime"
+	"mime/multipart"
 	"net/http"
 	"os"
 	"path/filepath"
@@ -331,6 +335,11 @@ func getLoggedRequest(req *testserver.Request, includedHeaders []string) LoggedR
 
 	if json.Valid(req.Body) {
 		result.Body = json.RawMessage(req.Body)
+	} else if normalized, ok := normalizeMultipartBody(req); ok {
+		// Multipart bodies contain a randomly generated boundary string and binary
+		// content; record a normalized form (sorted form-field names with sizes for
+		// file parts) so recorded requests stay deterministic and reviewable.
+		result.Body = normalized
 	} else {
 		result.RawBody = string(req.Body)
 	}
@@ -338,6 +347,55 @@ func getLoggedRequest(req *testserver.Request, includedHeaders []string) LoggedR
 	return result
 }
 
+// Multipart parts larger than this limit are summarized as a size placeholder
+// to keep recorded fixtures small. Reviewers care about *what* was uploaded
+// (path, format, overwrite flag), not the bytes themselves, for large blobs.
+const multipartContentLimit = 4096
+
+// normalizeMultipartBody returns a deterministic representation of a multipart
+// form body if the request's Content-Type is multipart/*. The second return
+// value is false if the body is not multipart or cannot be parsed.
+//
+// Text parts are recorded as their literal content so reviewers can read what
+// was uploaded; existing global UNIX_TIME / UUID / USERNAME replacements
+// normalize the timestamp / id / email fields embedded in deploy.lock and
+// similar payloads. Non-UTF-8 (binary) parts and parts whose serialized
+// content would bloat the recording past multipartContentLimit are
+// summarized as "[binary content N bytes]".
+func normalizeMultipartBody(req *testserver.Request) (any, bool) {
+	contentType := req.Headers.Get("Content-Type")
+	mediaType, params, err := mime.ParseMediaType(contentType)
+	if err != nil || !strings.HasPrefix(mediaType, "multipart/") {
+		return nil, false
+	}
+	boundary := params["boundary"]
+	if boundary == "" {
+		return nil, false
+	}
+	mr := multipart.NewReader(bytes.NewReader(req.Body), boundary)
+	parts := map[string]any{}
+	for {
+		part, err := mr.NextPart()
+		if err == io.EOF {
+			break
+		}
+		if err != nil {
+			return nil, false
+		}
+		data, err := io.ReadAll(part)
+		if err != nil {
+			return nil, false
+		}
+		name := part.FormName()
+		if !utf8.Valid(data) || len(data) > multipartContentLimit {
+			parts[name] = fmt.Sprintf("[binary content %d bytes]", len(data))
+			continue
+		}
+		parts[name] = string(data)
+	}
+	return map[string]any{"multipart_form": parts}, true
+}
+
 func filterHeaders(h http.Header, includedHeaders []string) http.Header {
 	headers := make(http.Header)
 	for k, v := range h {
diff --git a/acceptance/script.prepare b/acceptance/script.prepare
index a53627b231d..66080eb1fcb 100644
--- a/acceptance/script.prepare
+++ b/acceptance/script.prepare
@@ -128,6 +128,12 @@ print_telemetry_bool_values() {
     jq -r 'select(.path? == "/telemetry-ext") | (.body.protoLogs // [])[] | fromjson | ( (.entry // .) | (.databricks_cli_log.bundle_deploy_event.experimental.bool_values // []) ) | map("\(.key) \(.value)") | .[]' "$OUT_REQUESTS" | grep -Ev '^(engine_terraform_|deployment_history_enabled )' | sort
 }
 
+# Workspace paths uploaded via /workspace/import, one per line. The path is a
+# multipart form field, not part of the URL, so print_requests.py can't filter on it.
+print_workspace_imports() {
+    jq -r 'select(.path? == "/api/2.0/workspace/import") | .body.multipart_form.path | strings' "$OUT_REQUESTS"
+}
+
 sethome() {
     local home="$1"
     mkdir -p "$home"
diff --git a/cmd/air/runsubmit_test.go b/cmd/air/runsubmit_test.go
index b24740317af..5c5a2e7f23a 100644
--- a/cmd/air/runsubmit_test.go
+++ b/cmd/air/runsubmit_test.go
@@ -411,9 +411,11 @@ func TestSubmitWorkloadValidationOutcome(t *testing.T) {
 			t.Cleanup(server.Close)
 			var uploads, submissions atomic.Int32
 			server.Handle("POST", validateConfigPath, func(req testserver.Request) any { return tt.response })
-			server.Handle("POST", "/api/2.0/workspace-files/import-file/{path...}", func(req testserver.Request) any {
+			server.Handle("POST", "/api/2.0/workspace/import", func(req testserver.Request) any {
 				uploads.Add(1)
-				return req.Workspace.WorkspaceFilesImportFile(req.Vars["path"], req.Body, true)
+				form, err := testserver.ParseImportForm(req)
+				assert.NoError(t, err)
+				return req.Workspace.WorkspaceFilesImportFile(form.Path, form.Content, true)
 			})
 			server.Handle("POST", "/api/2.2/jobs/runs/submit", func(req testserver.Request) any {
 				submissions.Add(1)
@@ -730,18 +732,19 @@ func TestSubmitWorkloadPlainTarContentAddressed(t *testing.T) {
 	server.Handle("POST", "/api/2.2/jobs/runs/submit", func(req testserver.Request) any {
 		return jobs.SubmitRunResponse{RunId: 555}
 	})
-	// Count snapshot import-file calls, preserving fake-workspace persistence so the
+	// Count snapshot import calls, preserving fake-workspace persistence so the
 	// second submit's existence Stat sees the first upload. A count (not a set keyed by
 	// path) is what proves the skip: both submits resolve to the same content-addressed
 	// name, so a set could not tell a skipped second submit from one that re-uploaded to
 	// that same path.
 	snapshotUploads := 0
-	server.Handle("POST", "/api/2.0/workspace-files/import-file/{path...}", func(req testserver.Request) any {
-		p := req.Vars["path"]
-		if strings.Contains(p, "/.air/repo_snapshots/") {
+	server.Handle("POST", "/api/2.0/workspace/import", func(req testserver.Request) any {
+		form, err := testserver.ParseImportForm(req)
+		assert.NoError(t, err)
+		if strings.Contains(form.Path, "/.air/repo_snapshots/") {
 			snapshotUploads++
 		}
-		return req.Workspace.WorkspaceFilesImportFile(p, req.Body, req.URL.Query().Get("overwrite") == "true")
+		return req.Workspace.WorkspaceFilesImportFile(form.Path, form.Content, form.Overwrite)
 	})
 	stubValidateConfig(server)
 	testserver.AddDefaultHandlers(server)
@@ -778,7 +781,7 @@ code_source:
 	assert.Regexp(t, `^src_[0-9a-f]{16}\.tar\.gz$`, base)
 
 	// Same unchanged tree → identical remote path, and the second submit moved no bytes:
-	// zero new import-file calls (a real skip), not a re-upload to the same name.
+	// zero new import calls (a real skip), not a re-upload to the same name.
 	assert.Equal(t, first.CodeSourcePath, second.CodeSourcePath)
 	assert.Equal(t, afterFirst, snapshotUploads, "unchanged plain_tar should skip the second upload")
 	require.NotNil(t, first.SizeBytes)
@@ -808,12 +811,13 @@ func TestSubmitWorkloadGitArchiveCaching(t *testing.T) {
 	// Dedupe by path: the filer mkdirs-and-retries the import on a missing
 	// parent dir, so one logical upload can hit this route more than once.
 	uploaded := map[string]bool{}
-	server.Handle("POST", "/api/2.0/workspace-files/import-file/{path...}", func(req testserver.Request) any {
-		p := req.Vars["path"]
-		if strings.Contains(p, "/.air/repo_snapshots/") {
-			uploaded[p] = true
+	server.Handle("POST", "/api/2.0/workspace/import", func(req testserver.Request) any {
+		form, err := testserver.ParseImportForm(req)
+		assert.NoError(t, err)
+		if strings.Contains(form.Path, "/.air/repo_snapshots/") {
+			uploaded[form.Path] = true
 		}
-		return req.Workspace.WorkspaceFilesImportFile(p, req.Body, req.URL.Query().Get("overwrite") == "true")
+		return req.Workspace.WorkspaceFilesImportFile(form.Path, form.Content, form.Overwrite)
 	})
 	stubValidateConfig(server)
 	testserver.AddDefaultHandlers(server)
diff --git a/cmd/air/telemetry_test.go b/cmd/air/telemetry_test.go
index 35a0cad984d..49760d24ad9 100644
--- a/cmd/air/telemetry_test.go
+++ b/cmd/air/telemetry_test.go
@@ -61,10 +61,11 @@ func TestAirRunTelemetry(t *testing.T) {
 				return jobs.SubmitRunResponse{RunId: 555}
 			})
 			var uploadedSize int64
-			server.Handle("POST", "/api/2.0/workspace-files/import-file/{path...}", func(req testserver.Request) any {
-				p := req.Vars["path"]
-				if strings.HasSuffix(p, ".tar.gz") {
-					uploadedSize = int64(len(req.Body))
+			server.Handle("POST", "/api/2.0/workspace/import", func(req testserver.Request) any {
+				form, err := testserver.ParseImportForm(req)
+				assert.NoError(t, err)
+				if strings.HasSuffix(form.Path, ".tar.gz") {
+					uploadedSize = int64(len(form.Content))
 					time.Sleep(20 * time.Millisecond)
 					if tc.failUpload {
 						return testserver.Response{StatusCode: http.StatusForbidden, Body: map[string]string{
@@ -72,7 +73,7 @@ func TestAirRunTelemetry(t *testing.T) {
 						}}
 					}
 				}
-				return req.Workspace.WorkspaceFilesImportFile(p, req.Body, req.URL.Query().Get("overwrite") == "true")
+				return req.Workspace.WorkspaceFilesImportFile(form.Path, form.Content, form.Overwrite)
 			})
 			stubValidateConfig(server)
 			w, err := databricks.NewWorkspaceClient(&databricks.Config{Host: server.URL, Token: "token"})
diff --git a/libs/filer/workspace_files_client.go b/libs/filer/workspace_files_client.go
index e1b62481243..24188974ed4 100644
--- a/libs/filer/workspace_files_client.go
+++ b/libs/filer/workspace_files_client.go
@@ -9,10 +9,8 @@ import (
 	"io"
 	"io/fs"
 	"net/http"
-	"net/url"
 	"path"
 	"slices"
-	"strings"
 	"time"
 
 	"github.com/databricks/cli/libs/auth"
@@ -154,35 +152,29 @@ func (w *WorkspaceFilesClient) Write(ctx context.Context, name string, reader io
 		return err
 	}
 
-	// Remove leading "/" so we can use it in the URL.
-	overwrite := slices.Contains(mode, OverwriteIfExists)
-	urlPath := fmt.Sprintf(
-		"/api/2.0/workspace-files/import-file/%s?overwrite=%t",
-		url.PathEscape(strings.TrimLeft(absPath, "/")),
-		overwrite,
-	)
-
 	// Buffer the file contents because we may need to retry below and we cannot read twice.
 	body, err := io.ReadAll(reader)
 	if err != nil {
 		return err
 	}
 
-	err = w.apiClient.Do(ctx, http.MethodPost, urlPath, w.workspaceIDHeaders(), nil, body, nil)
+	// Upload with the SDK's multipart Workspace.Upload; format=AUTO lets the server
+	// classify each payload as file or notebook. The JSON-body workspace.Import caps
+	// content at 10 MB, the multipart form at the 500 MB workspace file limit.
+	opts := []workspace.UploadOption{workspace.UploadFormat(workspace.ImportFormatAuto)}
+	if slices.Contains(mode, OverwriteIfExists) {
+		opts = append(opts, workspace.UploadOverwrite())
+	}
+
+	err = w.workspaceClient.Workspace.Upload(ctx, absPath, bytes.NewReader(body), opts...)
 
 	// Return early on success.
 	if err == nil {
 		return nil
 	}
 
-	// Special handling of this error only if it is an API error.
-	aerr, ok := errors.AsType[*apierr.APIError](err)
-	if !ok {
-		return err
-	}
-
-	// This API returns a 404 if the parent directory does not exist.
-	if aerr.StatusCode == http.StatusNotFound {
+	// Parent directory does not exist.
+	if errors.Is(err, apierr.ErrNotFound) {
 		if !slices.Contains(mode, CreateParentDirectories) {
 			return noSuchDirectoryError{path.Dir(absPath)}
 		}
@@ -190,8 +182,8 @@ func (w *WorkspaceFilesClient) Write(ctx context.Context, name string, reader io
 		// Create parent directory.
 		err = w.workspaceClient.Workspace.MkdirsByPath(ctx, path.Dir(absPath))
 		if err != nil {
-			if mkdirErr, ok := errors.AsType[*apierr.APIError](err); ok && mkdirErr.StatusCode == http.StatusForbidden {
-				return permissionError{absPath, mkdirErr}
+			if errors.Is(err, apierr.ErrPermissionDenied) {
+				return permissionError{absPath, err}
 			}
 			return fmt.Errorf("unable to mkdir to write file %s: %w", absPath, err)
 		}
@@ -200,27 +192,32 @@ func (w *WorkspaceFilesClient) Write(ctx context.Context, name string, reader io
 		return w.Write(ctx, name, bytes.NewReader(body), sliceWithout(mode, CreateParentDirectories)...)
 	}
 
-	// This API returns 409 if the file already exists, when the object type is file
-	if aerr.StatusCode == http.StatusConflict {
+	// Path already taken. ErrResourceConflict covers every 409 (including the
+	// bare 409 with only a message); ErrResourceAlreadyExists covers the 400
+	// RESOURCE_ALREADY_EXISTS, which no status maps to a conflict.
+	if errors.Is(err, apierr.ErrResourceConflict) || errors.Is(err, apierr.ErrResourceAlreadyExists) {
 		return fileAlreadyExistsError{absPath}
 	}
-
-	// This API returns 400 if the file already exists when the object type is notebook.
-	// Both the historical "Path (<path>) already exists." format and the newer
-	// "RESOURCE_ALREADY_EXISTS: <path> already exists. ..." format end with the same
-	// "already exists." marker; the JSON error_code is empty in both. The new format
-	// might not have been rolled out to all workspaces yet, so we anchor on the shared
-	// marker and return absPath rather than parsing the message.
-	if aerr.StatusCode == http.StatusBadRequest && strings.Contains(aerr.Message, "already exists.") {
-		return fileAlreadyExistsError{absPath}
+	// Overwrite rejected because the existing object's node type differs from
+	// the upload. The collision carries an AIP-193 ErrorInfo with a stable
+	// reason, so branch on it rather than the message text.
+	if errors.Is(err, apierr.ErrInvalidParameterValue) {
+		if aerr, ok := errors.AsType[*apierr.APIError](err); ok {
+			if info := aerr.ErrorDetails().ErrorInfo; info != nil && info.Reason == "WORKSPACE_OBJECT_TYPE_MISMATCH" {
+				return fileAlreadyExistsError{absPath}
+			}
+		}
 	}
 
-	// This API returns StatusForbidden when you have read access but don't have write access to a file
-	if aerr.StatusCode == http.StatusForbidden {
-		return permissionError{absPath, aerr}
+	// Caller has read access but no write access.
+	if errors.Is(err, apierr.ErrPermissionDenied) {
+		return permissionError{absPath, err}
 	}
 
-	return err
+	// Any other failure (e.g. a server-side error with an empty message) is
+	// surfaced with the target path so the user can tell which upload failed;
+	// %w keeps the original error inspectable by callers.
+	return fmt.Errorf("failed to upload %s: %w", absPath, err)
 }
 
 func (w *WorkspaceFilesClient) Read(ctx context.Context, name string) (io.ReadCloser, error) {
diff --git a/libs/filer/workspace_files_client_test.go b/libs/filer/workspace_files_client_test.go
index 2915af60436..81832694d15 100644
--- a/libs/filer/workspace_files_client_test.go
+++ b/libs/filer/workspace_files_client_test.go
@@ -1,8 +1,11 @@
 package filer
 
 import (
+	"bytes"
 	"encoding/json"
 	"io/fs"
+	"net/http"
+	"strings"
 	"testing"
 	"time"
 
@@ -15,6 +18,8 @@ import (
 	"github.com/stretchr/testify/require"
 )
 
+// Confirms directory entries derived from workspace object infos report the
+// name, type, and size of each object type the workspace can return.
 func TestWorkspaceFilesDirEntry(t *testing.T) {
 	entries := wsfsDirEntriesFromObjectInfos([]workspace.ObjectInfo{
 		{
@@ -61,6 +66,8 @@ func TestWorkspaceFilesDirEntry(t *testing.T) {
 	assert.True(t, i2.IsDir())
 }
 
+// Confirms the workspace ID routing header is set only when the client config
+// carries a workspace ID, and that a nil workspace client yields no headers.
 func TestWorkspaceFilesClientWorkspaceIDHeaders(t *testing.T) {
 	tests := []struct {
 		name        string
@@ -97,6 +104,188 @@ func TestWorkspaceFilesClientWorkspaceIDHeaders(t *testing.T) {
 	})
 }
 
+// Confirms each error /workspace/import returns is translated to the filer's
+// own error type, and that unrecognized errors pass through unchanged. The
+// endpoint signals an occupied path with three different status/error_code
+// combinations (see the comment on Write), so all three are covered here to
+// pin the mapping the rest of the CLI relies on.
+func TestWorkspaceFilesClientWriteErrorMapping(t *testing.T) {
+	tests := []struct {
+		name            string
+		mode            []WriteMode
+		apiErr          *apierr.APIError
+		expectErrTarget any
+	}{
+		{
+			name:            "404 without create-parent maps to noSuchDirectoryError",
+			apiErr:          &apierr.APIError{StatusCode: http.StatusNotFound, Message: "not found"},
+			expectErrTarget: noSuchDirectoryError{},
+		},
+		{
+			name: "400 RESOURCE_ALREADY_EXISTS maps to fileAlreadyExistsError",
+			apiErr: &apierr.APIError{
+				StatusCode: http.StatusBadRequest,
+				ErrorCode:  "RESOURCE_ALREADY_EXISTS",
+				Message:    "/dir/file.txt already exists. Please pass overwrite=true to overwrite it.",
+			},
+			expectErrTarget: fileAlreadyExistsError{},
+		},
+		{
+			name: "409 ALREADY_EXISTS (concurrent contention) maps to fileAlreadyExistsError",
+			apiErr: &apierr.APIError{
+				StatusCode: http.StatusConflict,
+				ErrorCode:  "ALREADY_EXISTS",
+				Message:    "Node with name /dir/file.txt already exists. Please pass overwrite=true to update it.",
+			},
+			expectErrTarget: fileAlreadyExistsError{},
+		},
+		{
+			// A 409 carrying no error_code unwraps to ErrResourceConflict only,
+			// not to ErrAlreadyExists; the testserver returns exactly this shape.
+			name: "409 without error_code maps to fileAlreadyExistsError",
+			apiErr: &apierr.APIError{
+				StatusCode: http.StatusConflict,
+				Message:    "Node with name /dir/file.txt already exists.",
+			},
+			expectErrTarget: fileAlreadyExistsError{},
+		},
+		{
+			name: "400 INVALID_PARAMETER_VALUE other message passes through",
+			apiErr: &apierr.APIError{
+				StatusCode: http.StatusBadRequest,
+				ErrorCode:  "INVALID_PARAMETER_VALUE",
+				Message:    "some other validation failure",
+			},
+			expectErrTarget: nil,
+		},
+		{
+			name:            "403 maps to permissionError",
+			apiErr:          &apierr.APIError{StatusCode: http.StatusForbidden, Message: "denied"},
+			expectErrTarget: permissionError{},
+		},
+		{
+			name:            "500 passes through",
+			apiErr:          &apierr.APIError{StatusCode: http.StatusInternalServerError, Message: "boom"},
+			expectErrTarget: nil,
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			server := testserver.New(t)
+			server.Handle("POST", "/api/2.0/workspace/import", func(req testserver.Request) any {
+				return testserver.Response{
+					StatusCode: tc.apiErr.StatusCode,
+					Body: map[string]string{
+						"error_code": tc.apiErr.ErrorCode,
+						"message":    tc.apiErr.Message,
+					},
+				}
+			})
+			testserver.AddDefaultHandlers(server)
+
+			client, err := databricks.NewWorkspaceClient(&databricks.Config{
+				Host:  server.URL,
+				Token: "testtoken",
+			})
+			require.NoError(t, err)
+
+			f, err := NewWorkspaceFilesClient(client, "/dir")
+			require.NoError(t, err)
+
+			err = f.Write(t.Context(), "file.txt", bytes.NewReader([]byte("data")), tc.mode...)
+			require.Error(t, err)
+			switch target := tc.expectErrTarget.(type) {
+			case noSuchDirectoryError:
+				assert.ErrorAs(t, err, &target)
+			case fileAlreadyExistsError:
+				assert.ErrorAs(t, err, &target)
+			case permissionError:
+				assert.ErrorAs(t, err, &target)
+			case nil:
+				// passthrough — the underlying APIError stays inspectable,
+				// and the message names the file that failed to upload.
+				var aerr *apierr.APIError
+				require.ErrorAs(t, err, &aerr)
+				assert.Equal(t, tc.apiErr.StatusCode, aerr.StatusCode)
+				assert.Contains(t, err.Error(), "/dir/file.txt")
+			}
+		})
+	}
+}
+
+// writeWithImportError exercises Write through a real HTTP roundtrip so the
+// SDK parses AIP-193 error details from the response body (the errorDetails
+// field on apierr.APIError is unexported and only populated during response
+// parsing, so it cannot be set on a directly constructed APIError).
+func writeWithImportError(t *testing.T, body map[string]any) error {
+	t.Helper()
+
+	server := testserver.New(t)
+	server.Handle("POST", "/api/2.0/workspace/import", func(req testserver.Request) any {
+		return testserver.Response{
+			StatusCode: http.StatusBadRequest,
+			Body:       body,
+		}
+	})
+	testserver.AddDefaultHandlers(server)
+
+	client, err := databricks.NewWorkspaceClient(&databricks.Config{
+		Host:  server.URL,
+		Token: "testtoken",
+	})
+	require.NoError(t, err)
+
+	f, err := NewWorkspaceFilesClient(client, "/dir")
+	require.NoError(t, err)
+
+	err = f.Write(t.Context(), "file.txt", strings.NewReader("data"), OverwriteIfExists)
+	require.Error(t, err)
+	return err
+}
+
+// Confirms a type-mismatch collision is recognized from the structured
+// AIP-193 ErrorInfo reason, independent of the error message wording.
+func TestWorkspaceFilesClientWriteTypeMismatchReason(t *testing.T) {
+	// The message is deliberately unrelated to any collision wording, to prove
+	// the branch fires on the structured reason alone.
+	err := writeWithImportError(t, map[string]any{
+		"error_code": "INVALID_PARAMETER_VALUE",
+		"message":    "some future wording for the same condition",
+		"details": []map[string]any{
+			{
+				"@type":    "type.googleapis.com/google.rpc.ErrorInfo",
+				"reason":   "WORKSPACE_OBJECT_TYPE_MISMATCH",
+				"domain":   "workspace.databricks.com",
+				"metadata": map[string]string{"existing_type": "NOTEBOOK"},
+			},
+		},
+	})
+	var target fileAlreadyExistsError
+	assert.ErrorAs(t, err, &target)
+}
+
+// Confirms an ErrorInfo carrying some other reason is not mistaken for a path
+// collision, so the reason check above cannot swallow unrelated failures.
+func TestWorkspaceFilesClientWriteUnrelatedReasonPassesThrough(t *testing.T) {
+	err := writeWithImportError(t, map[string]any{
+		"error_code": "INVALID_PARAMETER_VALUE",
+		"message":    "some other validation failure",
+		"details": []map[string]any{
+			{
+				"@type":  "type.googleapis.com/google.rpc.ErrorInfo",
+				"reason": "SOME_OTHER_REASON",
+				"domain": "workspace.databricks.com",
+			},
+		},
+	})
+	var aerr *apierr.APIError
+	require.ErrorAs(t, err, &aerr)
+	assert.Equal(t, http.StatusBadRequest, aerr.StatusCode)
+}
+
+// Confirms a workspace get-status payload unmarshals into wsfsFileInfo and that
+// the fs.FileInfo methods derived from it report the expected values.
 func TestWorkspaceFilesClient_wsfsUnmarshal(t *testing.T) {
 	payload := `
 		{
@@ -163,6 +352,8 @@ func statWithError(t *testing.T, statusCode int, errorCode string) error {
 	return err
 }
 
+// Confirms a 403 from get-status surfaces as an APIError rather than being
+// remapped, so callers can distinguish it from a missing file.
 func TestWorkspaceFilesClientStatForbidden(t *testing.T) {
 	err := statWithError(t, 403, "PERMISSION_DENIED")
 	var apiErr *apierr.APIError
@@ -170,6 +361,8 @@ func TestWorkspaceFilesClientStatForbidden(t *testing.T) {
 	assert.Equal(t, 403, apiErr.StatusCode)
 }
 
+// Confirms a 500 from get-status surfaces as an APIError and is not treated as
+// a missing file.
 func TestWorkspaceFilesClientStatInternalError(t *testing.T) {
 	err := statWithError(t, 500, "INTERNAL_ERROR")
 	var apiErr *apierr.APIError
@@ -177,6 +370,8 @@ func TestWorkspaceFilesClientStatInternalError(t *testing.T) {
 	assert.Equal(t, 500, apiErr.StatusCode)
 }
 
+// Confirms RESOURCE_DOES_NOT_EXIST maps to fs.ErrNotExist so the filer plugs
+// into the io/fs error conventions callers check against.
 func TestWorkspaceFilesClientStatNotFound(t *testing.T) {
 	err := statWithError(t, 404, "RESOURCE_DOES_NOT_EXIST")
 	assert.ErrorIs(t, err, fs.ErrNotExist)
diff --git a/libs/sync/watchdog.go b/libs/sync/watchdog.go
index d3bb57662d9..fa7ff0baceb 100644
--- a/libs/sync/watchdog.go
+++ b/libs/sync/watchdog.go
@@ -10,7 +10,10 @@ import (
 	"golang.org/x/sync/errgroup"
 )
 
-// Maximum number of concurrent requests during sync.
+// Maximum number of concurrent requests during sync. Chosen against the
+// per-endpoint rate limits documented at
+// https://docs.databricks.com/aws/en/resources/limits ("API rate limits" -
+// Workspace API), which sync stays within for the endpoints it calls.
 const MaxRequestsInFlight = 20
 
 // Delete the specified path.
diff --git a/libs/testserver/fake_workspace.go b/libs/testserver/fake_workspace.go
index f478f25c3a2..9daf7dee96f 100644
--- a/libs/testserver/fake_workspace.go
+++ b/libs/testserver/fake_workspace.go
@@ -882,6 +882,35 @@ func (s *FakeWorkspace) hasChildren(dirPath string) bool {
 	return false
 }
 
+// detectNotebookLanguage mirrors the real /workspace/import format=AUTO logic:
+// a file whose extension is .py / .sql / .scala / .r and whose content starts
+// with the language-appropriate "Databricks notebook source" line-comment is
+// stored as a NOTEBOOK with the corresponding language; otherwise it's a FILE.
+//
+// The extension is lowercased because the real endpoint matches it
+// case-insensitively, and ".R" is the conventional spelling for R sources.
+func detectNotebookLanguage(extension string, body []byte) (workspace.Language, bool) {
+	switch strings.ToLower(extension) {
+	case ".py":
+		if bytes.HasPrefix(body, []byte("# Databricks notebook source")) {
+			return workspace.LanguagePython, true
+		}
+	case ".sql":
+		if bytes.HasPrefix(body, []byte("-- Databricks notebook source")) {
+			return workspace.LanguageSql, true
+		}
+	case ".scala":
+		if bytes.HasPrefix(body, []byte("// Databricks notebook source")) {
+			return workspace.LanguageScala, true
+		}
+	case ".r":
+		if bytes.HasPrefix(body, []byte("# Databricks notebook source")) {
+			return workspace.LanguageR, true
+		}
+	}
+	return "", false
+}
+
 func (s *FakeWorkspace) WorkspaceFilesImportFile(filePath string, body []byte, overwrite bool) Response {
 	if !strings.HasPrefix(filePath, "/") {
 		filePath = "/" + filePath
@@ -904,18 +933,19 @@ func (s *FakeWorkspace) WorkspaceFilesImportFile(filePath string, body []byte, o
 		}
 	}
 
-	// Note: Files with .py, .scala, .r or .sql extension can
-	// be notebooks if they contain a magical "Databricks notebook source"
-	// header comment. We omit support non-python extensions for now for simplicity.
+	// Files with .py / .sql / .scala / .r extension can be notebooks if they
+	// carry the "Databricks notebook source" header comment in the language's
+	// line-comment syntax. Mirror the real workspace's auto-detection here so
+	// acceptance tests can assert the resulting object_type via /workspace/list.
 	extension := filepath.Ext(filePath)
-	if extension == ".py" && strings.HasPrefix(string(body), "# Databricks notebook source") {
+	if lang, isNotebook := detectNotebookLanguage(extension, body); isNotebook {
 		// Notebooks are stripped of their extension by the workspace import API.
 		workspacePath = strings.TrimSuffix(filePath, extension)
 		s.files[workspacePath] = FileEntry{
 			Info: workspace.ObjectInfo{
 				ObjectType: "NOTEBOOK",
 				Path:       workspacePath,
-				Language:   "PYTHON",
+				Language:   lang,
 				ObjectId:   nextID(),
 			},
 			Data: body,
diff --git a/libs/testserver/fault.go b/libs/testserver/fault.go
index 75d3092bb70..43d46f3f28c 100644
--- a/libs/testserver/fault.go
+++ b/libs/testserver/fault.go
@@ -1,6 +1,7 @@
 package testserver
 
 import (
+	"bytes"
 	"encoding/json"
 	"strings"
 	"sync"
@@ -19,6 +20,12 @@ type FaultRule struct {
 	AfterHandler bool
 	offset       int
 	times        int
+
+	// bodyContains, if non-empty, additionally requires the request body to
+	// contain this substring for the rule to fire. /workspace/import routes
+	// every upload through the same method+path, so the only way to target a
+	// single file's upload is by matching its multipart "path" form field.
+	bodyContains string
 }
 
 // FaultRules holds the active fault injection rules for a test server.
@@ -33,16 +40,16 @@ func NewFaultRules() *FaultRules {
 }
 
 // Set registers or replaces a fault rule for the given token and pattern.
-func (fr *FaultRules) Set(token, pattern string, statusCode int, body string, offset, times int) {
-	fr.set(token, pattern, statusCode, body, offset, times, false)
+func (fr *FaultRules) Set(token, pattern string, statusCode int, body string, offset, times int, bodyContains string) {
+	fr.set(token, pattern, statusCode, body, offset, times, false, bodyContains)
 }
 
 // SetAfterHandler is like Set, but the handler runs first so its effect is kept.
-func (fr *FaultRules) SetAfterHandler(token, pattern string, statusCode int, body string, offset, times int) {
-	fr.set(token, pattern, statusCode, body, offset, times, true)
+func (fr *FaultRules) SetAfterHandler(token, pattern string, statusCode int, body string, offset, times int, bodyContains string) {
+	fr.set(token, pattern, statusCode, body, offset, times, true, bodyContains)
 }
 
-func (fr *FaultRules) set(token, pattern string, statusCode int, body string, offset, times int, afterHandler bool) {
+func (fr *FaultRules) set(token, pattern string, statusCode int, body string, offset, times int, afterHandler bool, bodyContains string) {
 	fr.mu.Lock()
 	defer fr.mu.Unlock()
 	fr.rules[faultRuleKey{token: token, pattern: pattern}] = &FaultRule{
@@ -51,12 +58,14 @@ func (fr *FaultRules) set(token, pattern string, statusCode int, body string, of
 		AfterHandler: afterHandler,
 		offset:       offset,
 		times:        times,
+		bodyContains: bodyContains,
 	}
 }
 
 // Check returns a matching fault rule and advances its counters, or nil if no rule matches.
 // Pattern supports a trailing "*" wildcard, e.g. "PUT /api/2.0/permissions/pipelines/*".
-func (fr *FaultRules) Check(method, path, token string) *FaultRule {
+// A rule with a non-empty bodyContains only matches when body contains that substring.
+func (fr *FaultRules) Check(method, path, token string, body []byte) *FaultRule {
 	requestPattern := method + " " + path
 
 	fr.mu.Lock()
@@ -76,6 +85,11 @@ func (fr *FaultRules) Check(method, path, token string) *FaultRule {
 		if !matched {
 			continue
 		}
+		// A non-matching body must not consume the rule's offset/times budget,
+		// so this check precedes the counter updates below.
+		if rule.bodyContains != "" && !bytes.Contains(body, []byte(rule.bodyContains)) {
+			continue
+		}
 		if rule.offset > 0 {
 			rule.offset--
 			return nil
@@ -105,14 +119,15 @@ func faultEndpointHandler(fr *FaultRules) HandlerFunc {
 			Offset       int    `json:"offset"`
 			Times        int    `json:"times"`
 			AfterHandler bool   `json:"after_handler"`
+			BodyContains string `json:"body_contains"`
 		}
 		if err := json.Unmarshal(req.Body, &body); err != nil {
 			return Response{StatusCode: 400, Body: map[string]string{"error": err.Error()}}
 		}
 		if body.AfterHandler {
-			fr.SetAfterHandler(req.Token, body.Pattern, body.StatusCode, body.Body, body.Offset, body.Times)
+			fr.SetAfterHandler(req.Token, body.Pattern, body.StatusCode, body.Body, body.Offset, body.Times, body.BodyContains)
 		} else {
-			fr.Set(req.Token, body.Pattern, body.StatusCode, body.Body, body.Offset, body.Times)
+			fr.Set(req.Token, body.Pattern, body.StatusCode, body.Body, body.Offset, body.Times, body.BodyContains)
 		}
 		return Response{StatusCode: 200}
 	}
diff --git a/libs/testserver/fault_test.go b/libs/testserver/fault_test.go
index db41b74d3ba..ae27b954f93 100644
--- a/libs/testserver/fault_test.go
+++ b/libs/testserver/fault_test.go
@@ -14,18 +14,18 @@ import (
 
 func TestFaultRulesNoMatch(t *testing.T) {
 	fr := testserver.NewFaultRules()
-	fr.Set("tok", "GET /foo", 504, "body", 0, 1)
+	fr.Set("tok", "GET /foo", 504, "body", 0, 1, "")
 
-	assert.Nil(t, fr.Check("POST", "/foo", "tok"))
-	assert.Nil(t, fr.Check("GET", "/bar", "tok"))
-	assert.Nil(t, fr.Check("GET", "/foo", "other"))
+	assert.Nil(t, fr.Check("POST", "/foo", "tok", nil))
+	assert.Nil(t, fr.Check("GET", "/bar", "tok", nil))
+	assert.Nil(t, fr.Check("GET", "/foo", "other", nil))
 }
 
 func TestFaultRulesExactMatch(t *testing.T) {
 	fr := testserver.NewFaultRules()
-	fr.Set("tok", "PUT /api/2.0/jobs/123", 504, "body", 0, 1)
+	fr.Set("tok", "PUT /api/2.0/jobs/123", 504, "body", 0, 1, "")
 
-	rule := fr.Check("PUT", "/api/2.0/jobs/123", "tok")
+	rule := fr.Check("PUT", "/api/2.0/jobs/123", "tok", nil)
 	require.NotNil(t, rule)
 	assert.Equal(t, 504, rule.StatusCode)
 	assert.Equal(t, "body", rule.Body)
@@ -33,31 +33,43 @@ func TestFaultRulesExactMatch(t *testing.T) {
 
 func TestFaultRulesWildcardMatch(t *testing.T) {
 	fr := testserver.NewFaultRules()
-	fr.Set("tok", "PUT /api/2.0/permissions/pipelines/*", 504, "body", 0, 2)
+	fr.Set("tok", "PUT /api/2.0/permissions/pipelines/*", 504, "body", 0, 2, "")
 
-	assert.NotNil(t, fr.Check("PUT", "/api/2.0/permissions/pipelines/abc", "tok"))
-	assert.NotNil(t, fr.Check("PUT", "/api/2.0/permissions/pipelines/xyz", "tok"))
-	assert.Nil(t, fr.Check("PUT", "/api/2.0/permissions/pipelines/xyz", "tok")) // exhausted
+	assert.NotNil(t, fr.Check("PUT", "/api/2.0/permissions/pipelines/abc", "tok", nil))
+	assert.NotNil(t, fr.Check("PUT", "/api/2.0/permissions/pipelines/xyz", "tok", nil))
+	assert.Nil(t, fr.Check("PUT", "/api/2.0/permissions/pipelines/xyz", "tok", nil)) // exhausted
 }
 
 func TestFaultRulesOffset(t *testing.T) {
 	fr := testserver.NewFaultRules()
-	fr.Set("tok", "GET /foo", 504, "body", 2, 1)
+	fr.Set("tok", "GET /foo", 504, "body", 2, 1, "")
 
-	assert.Nil(t, fr.Check("GET", "/foo", "tok"))    // offset 2→1
-	assert.Nil(t, fr.Check("GET", "/foo", "tok"))    // offset 1→0
-	assert.NotNil(t, fr.Check("GET", "/foo", "tok")) // fires
-	assert.Nil(t, fr.Check("GET", "/foo", "tok"))    // exhausted
+	assert.Nil(t, fr.Check("GET", "/foo", "tok", nil))    // offset 2→1
+	assert.Nil(t, fr.Check("GET", "/foo", "tok", nil))    // offset 1→0
+	assert.NotNil(t, fr.Check("GET", "/foo", "tok", nil)) // fires
+	assert.Nil(t, fr.Check("GET", "/foo", "tok", nil))    // exhausted
 }
 
 func TestFaultRulesTimes(t *testing.T) {
 	fr := testserver.NewFaultRules()
-	fr.Set("tok", "GET /foo", 504, "body", 0, 3)
+	fr.Set("tok", "GET /foo", 504, "body", 0, 3, "")
 
 	for range 3 {
-		assert.NotNil(t, fr.Check("GET", "/foo", "tok"))
+		assert.NotNil(t, fr.Check("GET", "/foo", "tok", nil))
 	}
-	assert.Nil(t, fr.Check("GET", "/foo", "tok")) // exhausted
+	assert.Nil(t, fr.Check("GET", "/foo", "tok", nil)) // exhausted
+}
+
+func TestFaultRulesBodyContains(t *testing.T) {
+	fr := testserver.NewFaultRules()
+	fr.Set("tok", "POST /api/2.0/workspace/import", 403, "body", 0, 1, "state/resources.json")
+
+	// Body without the substring must not match and must not consume the budget.
+	assert.Nil(t, fr.Check("POST", "/api/2.0/workspace/import", "tok", []byte("path=state/deploy.lock")))
+	// Body with the substring fires.
+	assert.NotNil(t, fr.Check("POST", "/api/2.0/workspace/import", "tok", []byte("path=state/resources.json")))
+	// Budget was only consumed by the matching request.
+	assert.Nil(t, fr.Check("POST", "/api/2.0/workspace/import", "tok", []byte("path=state/resources.json")))
 }
 
 func TestServerFaultAfterHandlerKeepsTheHandlersEffect(t *testing.T) {
diff --git a/libs/testserver/handlers.go b/libs/testserver/handlers.go
index a8217e3bb20..9e060e288b4 100644
--- a/libs/testserver/handlers.go
+++ b/libs/testserver/handlers.go
@@ -29,6 +29,47 @@ var TestMetastore = catalog.MetastoreAssignment{
 	WorkspaceId:        TestWorkspaceID,
 }
 
+// ImportForm holds the fields of a multipart /workspace/import request.
+type ImportForm struct {
+	Path      string
+	Content   []byte
+	Format    string
+	Overwrite bool
+}
+
+// ParseImportForm parses the multipart body of a /workspace/import request.
+func ParseImportForm(req Request) (ImportForm, error) {
+	var form ImportForm
+	_, params, err := mime.ParseMediaType(req.Headers.Get("Content-Type"))
+	if err != nil {
+		return form, err
+	}
+	mr := multipart.NewReader(bytes.NewReader(req.Body), params["boundary"])
+	for {
+		part, err := mr.NextPart()
+		if err == io.EOF {
+			return form, nil
+		}
+		if err != nil {
+			return form, err
+		}
+		data, err := io.ReadAll(part)
+		if err != nil {
+			return form, err
+		}
+		switch part.FormName() {
+		case "path":
+			form.Path = string(data)
+		case "content":
+			form.Content = data
+		case "format":
+			form.Format = string(data)
+		case "overwrite":
+			form.Overwrite = string(data) == "true"
+		}
+	}
+}
+
 func AddDefaultHandlers(server *Server) {
 	server.Handle("GET", "/api/2.0/policies/clusters/list", func(req Request) any {
 		return req.Workspace.ClusterPoliciesList(req)
@@ -153,6 +194,54 @@ func AddDefaultHandlers(server *Server) {
 	})
 
 	server.Handle("POST", "/api/2.0/workspace/import", func(req Request) any {
+		// /workspace/import accepts both a JSON body (matching workspace.Import) and a
+		// multipart form body. The multipart variant is what databricks-sdk-go's
+		// Workspace.Upload uses; the JSON variant is kept for back-compat with anything
+		// that still hits Workspace.Import directly.
+		mediaType, _, _ := mime.ParseMediaType(req.Headers.Get("Content-Type"))
+		if strings.HasPrefix(mediaType, "multipart/") {
+			form, err := ParseImportForm(req)
+			if err != nil {
+				return Response{
+					Body:       fmt.Sprintf("internal error: %s", err),
+					StatusCode: http.StatusInternalServerError,
+				}
+			}
+
+			// Require format explicitly: the real endpoint defaults to SOURCE, which
+			// would import every upload as a notebook, so a caller that drops the
+			// field is a bug rather than a request for the fake's usual behavior.
+			if form.Format != string(workspace.ImportFormatAuto) {
+				return Response{
+					Body:       fmt.Sprintf("internal error: The test server only supports auto format, got %q.", form.Format),
+					StatusCode: http.StatusInternalServerError,
+				}
+			}
+
+			// Translate any 409 from the shared fake into the 400 + errorCode
+			// RESOURCE_ALREADY_EXISTS shape returned by the real /workspace/import
+			// endpoint, including the AIP-193 ErrorInfo detail it attaches to path
+			// collisions (universe PR #2019174, WP-6031).
+			resp := req.Workspace.WorkspaceFilesImportFile(form.Path, form.Content, form.Overwrite)
+			if resp.StatusCode == http.StatusConflict {
+				return Response{
+					StatusCode: http.StatusBadRequest,
+					Body: map[string]any{
+						"error_code": "RESOURCE_ALREADY_EXISTS",
+						"message":    fmt.Sprintf("Path (%s) already exists.", form.Path),
+						"details": []map[string]any{
+							{
+								"@type":  "type.googleapis.com/google.rpc.ErrorInfo",
+								"reason": "RESOURCE_ALREADY_EXISTS",
+								"domain": "workspace.databricks.com",
+							},
+						},
+					},
+				}
+			}
+			return resp
+		}
+
 		var request workspace.Import
 		err := json.Unmarshal(req.Body, &request)
 		if err != nil {
diff --git a/libs/testserver/server.go b/libs/testserver/server.go
index 1f56717c50a..5170b318818 100644
--- a/libs/testserver/server.go
+++ b/libs/testserver/server.go
@@ -372,7 +372,7 @@ func (s *Server) serve(w http.ResponseWriter, r *http.Request, handler HandlerFu
 
 	var resp EncodedResponse
 
-	fault := s.faults.Check(r.Method, r.URL.Path, token)
+	fault := s.faults.Check(r.Method, r.URL.Path, token, request.Body)
 
 	if fault == nil || fault.AfterHandler {
 		if bytes.Contains(request.Body, []byte("INJECT_ERROR")) {
diff --git a/libs/testserver/workspace_test.go b/libs/testserver/workspace_test.go
index cde1c9741c6..401758c6648 100644
--- a/libs/testserver/workspace_test.go
+++ b/libs/testserver/workspace_test.go
@@ -88,6 +88,24 @@ func TestWorkspaceDeleteNonRecursiveRequiresEmptyDirectory(t *testing.T) {
 	assert.Equal(t, 404, getStatus(t, server.URL, "/a/b"))
 }
 
+// format=AUTO matches the extension case-insensitively, so ".R" — the
+// conventional spelling for R sources — is detected as a notebook just like
+// ".r". Notebooks are stored with the extension stripped.
+func TestWorkspaceImportDetectsNotebookExtensionCaseInsensitively(t *testing.T) {
+	server := testserver.New(t)
+	testserver.AddDefaultHandlers(server)
+
+	mkdirs(t, server.URL, "/test-dir")
+
+	for _, name := range []string{"lower.r", "upper.R"} {
+		require.Equal(t, 200, importFile(t, server.URL, "/test-dir/"+name, "# Databricks notebook source\n"), name)
+	}
+
+	// Both land at the extension-stripped path, which only happens for notebooks.
+	assert.Equal(t, 200, getStatus(t, server.URL, "/test-dir/lower"))
+	assert.Equal(t, 200, getStatus(t, server.URL, "/test-dir/upper"))
+}
+
 // mkdirs creates all intermediate directories, matching "mkdir -p".
 func TestWorkspaceMkdirsRecursive(t *testing.T) {
 	server := testserver.New(t)