diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 8d8ad82..05bf7cf 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -7,10 +7,31 @@ on:
 
 jobs:
   test:
-    runs-on: ubuntu-latest
+    name: ${{ matrix.os }} py${{ matrix.python-version }}
+    runs-on: ${{ matrix.os }}
+    defaults:
+      run:
+        # bash on every platform, so the wheel glob and paths below behave the
+        # same way. Git Bash ships on the Windows runners.
+        shell: bash
     strategy:
+      # One platform failing should not hide the others.
+      fail-fast: false
       matrix:
+        os: [ubuntu-latest]
         python-version: ["3.9", "3.10", "3.11", "3.12", "3.13"]
+        include:
+          # Windows and macOS at the supported floor and ceiling. Console
+          # encoding and path handling are where they diverge from Linux, and
+          # both sit on the CLI's hot path -- a check prints "<name> ✓", so the
+          # curriculum's own output has to survive the console it lands on.
+          # Ubuntu covers the versions in between.
+          - os: windows-latest
+            python-version: "3.9"
+          - os: windows-latest
+            python-version: "3.13"
+          - os: macos-latest
+            python-version: "3.13"
     steps:
       - uses: actions/checkout@v4
       - uses: actions/setup-python@v5
@@ -22,5 +43,13 @@ jobs:
       - run: python -m pip install build
       - run: python -m build
       - run: python -m pip install --force-reinstall dist/*.whl
-      - run: pythonlings init --path /tmp/pythonlings-workspace
-      - run: pythonlings --root /tmp/pythonlings-workspace list
+      - run: pythonlings init --path "${{ runner.temp }}/pythonlings-workspace"
+      - run: pythonlings --root "${{ runner.temp }}/pythonlings-workspace" list
+      - name: CLI survives a non-UTF-8 console
+        # The regression that motivated Windows coverage: status glyphs and
+        # captured check output crashed on consoles that cannot encode them.
+        env:
+          PYTHONIOENCODING: ascii
+        run: |
+          pythonlings --root tests/fixtures/passing_curriculum verify
+          pythonlings --root "${{ runner.temp }}/pythonlings-workspace" list
diff --git a/pythonlings/core/doctor.py b/pythonlings/core/doctor.py
index 0f3529c..bbaf145 100644
--- a/pythonlings/core/doctor.py
+++ b/pythonlings/core/doctor.py
@@ -114,7 +114,10 @@ def _check_workspace(root: Path) -> CheckResult:
     try:
         mode = root.stat().st_mode
     except OSError as exc:
-        if exc.errno == errno.ELOOP:
+        # Windows reports an unresolvable path (a symlink loop among them) as
+        # ERROR_CANT_RESOLVE_FILENAME with no matching errno, so match on the
+        # winerror too rather than letting it escape.
+        if exc.errno == errno.ELOOP or getattr(exc, "winerror", None) == 1921:
             return CheckResult(
                 "Workspace",
                 CheckStatus.FAILURE,
@@ -126,7 +129,13 @@ def _check_workspace(root: Path) -> CheckResult:
                 CheckStatus.FAILURE,
                 f"{root} does not exist; run `pythonlings init --path {root}`",
             )
-        raise
+        # Anything else is still reported rather than raised: doctor exists to
+        # describe a broken workspace, so it must not crash on one.
+        return CheckResult(
+            "Workspace",
+            CheckStatus.FAILURE,
+            f"{root} could not be read ({exc.strerror or exc})",
+        )
     if not stat.S_ISDIR(mode):
         return CheckResult(
             "Workspace", CheckStatus.FAILURE, f"{root} is not a directory"
diff --git a/tests/integration/test_cli_doctor.py b/tests/integration/test_cli_doctor.py
index 8dcaa5f..3ea8717 100644
--- a/tests/integration/test_cli_doctor.py
+++ b/tests/integration/test_cli_doctor.py
@@ -174,8 +174,12 @@ def test_doctor_unknown_home_user_is_friendly() -> None:
 
     assert result.returncode == 1
     assert "[FAIL] Workspace:" in result.stdout
-    assert root in result.stdout
-    assert "check the path and symlinks" in result.stdout
+    # POSIX leaves an unknown ~user unexpanded, so the path stays literal and
+    # doctor reports it as unresolvable. Windows expands it to a path under the
+    # users directory, which is merely missing. Both are correct, so assert what
+    # holds either way -- a reported failure naming the user -- rather than
+    # pinning one platform's wording.
+    assert "pythonlings_no_such_user_93847" in result.stdout
     assert "Traceback" not in result.stdout + result.stderr
 
 
diff --git a/tests/integration/test_cli_verify.py b/tests/integration/test_cli_verify.py
index def55e8..599c3cb 100644
--- a/tests/integration/test_cli_verify.py
+++ b/tests/integration/test_cli_verify.py
@@ -214,6 +214,10 @@ def test_verify_keeps_unicode_symbol_under_utf8(tmp_path: Path) -> None:
         [sys.executable, "-m", "pythonlings", "--root", str(tmp_path), "verify"],
         capture_output=True,
         text=True,
+        # The child writes UTF-8 because of PYTHONIOENCODING above; decode it
+        # the same way rather than falling back to the parent's locale, which
+        # is not UTF-8 on Windows.
+        encoding="utf-8",
         env=env,
     )
 
diff --git a/tests/unit/test_manifest.py b/tests/unit/test_manifest.py
index 6b142cc..e27157d 100644
--- a/tests/unit/test_manifest.py
+++ b/tests/unit/test_manifest.py
@@ -95,7 +95,8 @@ def test_load_rejects_missing_exercise_path(tmp_path: Path) -> None:
         'hint = "h"\n',
         encoding="utf-8",
     )
-    with pytest.raises(ManifestError, match="exercises/missing.py"):
+    # The message echoes the path with the platform's separator.
+    with pytest.raises(ManifestError, match=r"exercises[\\/]missing\.py"):
         load(tmp_path)