diff --git a/changelog/798.bugfix.rst b/changelog/798.bugfix.rst
new file mode 100644
index 00000000..f37760ab
--- /dev/null
+++ b/changelog/798.bugfix.rst
@@ -0,0 +1 @@
+Ensure outer hook wrappers receive the error and complete teardown when a new-style hook wrapper yields more than once.
diff --git a/src/pluggy/_execution.py b/src/pluggy/_execution.py
index 0e62b4d3..f3511e1d 100644
--- a/src/pluggy/_execution.py
+++ b/src/pluggy/_execution.py
@@ -182,6 +182,7 @@ def _multicall(
                 # Try to force finalizers otherwise postponed till GC action.
                 # Note: close() may raise if generator handles GeneratorExit.
                 teardown.close()
+                _raise_wrapfail(teardown, "has second yield")
             except StopIteration as si:
                 result = si.value
                 exception = None
@@ -189,7 +190,6 @@ def _multicall(
             except BaseException as e:
                 exception = e
                 continue
-            _raise_wrapfail(teardown, "has second yield")
 
     if exception is not None:
         raise exception
diff --git a/testing/test_multicall.py b/testing/test_multicall.py
index e400e85a..3df81e70 100644
--- a/testing/test_multicall.py
+++ b/testing/test_multicall.py
@@ -142,6 +142,56 @@ def m():
         MC([m], {})
 
 
+@pytest.mark.parametrize("old_style_outer", [False, True])
+@pytest.mark.parametrize("hook_raises", [False, True])
+def test_wrapper_two_yields_unwinds_outer_wrappers(
+    old_style_outer: bool, hook_raises: bool
+) -> None:
+    out = []
+    errors = []
+
+    @hookimpl
+    def impl():
+        if hook_raises:
+            raise ValueError("hook failed")
+        return 1
+
+    @hookimpl(wrapper=True)
+    def inner():
+        try:
+            try:
+                yield
+            except ValueError:
+                pass
+            yield
+        finally:
+            out.append("inner cleanup")
+
+    @hookimpl(wrapper=not old_style_outer, hookwrapper=old_style_outer)
+    def outer():
+        try:
+            if old_style_outer:
+                outcome = yield
+                errors.append(outcome.exception)
+            else:
+                try:
+                    yield
+                except RuntimeError as exc:
+                    errors.append(exc)
+                    raise
+        finally:
+            out.append("outer cleanup")
+
+    with pytest.raises(RuntimeError, match="has second yield") as excinfo:
+        try:
+            MC([impl, inner, outer], {})
+        finally:
+            out.append("caller cleanup")
+
+    assert errors == [excinfo.value]
+    assert out == ["inner cleanup", "outer cleanup", "caller cleanup"]
+
+
 def test_hookwrapper_order() -> None:
     out = []