prevent Config.add_cleanup callbacks preventing other cleanups running

src/_pytest/config/__init__.py

@@ -5,6 +5,7 @@
 
 import argparse
 import collections.abc
+import contextlib
 import copy
 import dataclasses
 import enum
@@ -33,6 +34,7 @@
 from typing import TextIO
 from typing import Type
 from typing import TYPE_CHECKING
+from typing import TypeVar
 import warnings
 
 import pluggy
@@ -73,6 +75,8 @@
     from _pytest.cacheprovider import Cache
     from _pytest.terminal import TerminalReporter
 
+_T_callback = TypeVar("_T_callback", bound=Callable[[], None])
+
 
 _PluggyPlugin = object
 """A type to represent plugin objects.
@@ -1085,6 +1089,7 @@ def __init__(
         )
         self.args_source = Config.ArgsSource.ARGS
         self.args: list[str] = []
+        self._exit_stack = contextlib.ExitStack()
 
     @property
     def rootpath(self) -> pathlib.Path:
@@ -1104,10 +1109,11 @@ def inipath(self) -> pathlib.Path | None:
         """
         return self._inipath
 
-    def add_cleanup(self, func: Callable[[], None]) -> None:
+    def add_cleanup(self, func: _T_callback) -> _T_callback:
         """Add a function to be called when the config object gets out of
         use (usually coinciding with pytest_unconfigure)."""
-        self._cleanup.append(func)
+        self._exit_stack.callback(func)
+        return func
 
     def _do_configure(self) -> None:
         assert not self._configured
@@ -1117,13 +1123,18 @@ def _do_configure(self) -> None:
             self.hook.pytest_configure.call_historic(kwargs=dict(config=self))
 
     def _ensure_unconfigure(self) -> None:
-        if self._configured:
-            self._configured = False
-            self.hook.pytest_unconfigure(config=self)
-            self.hook.pytest_configure._call_history = []
-        while self._cleanup:
-            fin = self._cleanup.pop()
-            fin()
+        try:
+            if self._configured:
+                self._configured = False
+                try:
+                    self.hook.pytest_unconfigure(config=self)
+                finally:
+                    self.hook.pytest_configure._call_history = []
+        finally:
+            try:
+                self._exit_stack.close()
+            finally:
+                self._exit_stack = contextlib.ExitStack()
 
     def get_terminal_writer(self) -> TerminalWriter:
         terminalreporter: TerminalReporter | None = self.pluginmanager.get_plugin(

testing/test_config.py

@@ -983,6 +983,37 @@ def test_confcutdir_check_isdir(self, pytester: Pytester) -> None:
     def test_iter_rewritable_modules(self, names, expected) -> None:
         assert list(_iter_rewritable_modules(names)) == expected
 
+    def test_add_cleanup(self, pytester: Pytester) -> None:
+        config = Config.fromdictargs({}, [])
+        config._do_configure()
+        report = []
+
+        class MyError(BaseException):
+            pass
+
+        @config.add_cleanup
+        def cleanup_last():
+            report.append("cleanup_last")
+
+        @config.add_cleanup
+        def raise_2():
+            report.append("raise_2")
+            raise MyError("raise_2")
+
+        @config.add_cleanup
+        def raise_1():
+            report.append("raise_1")
+            raise MyError("raise_1")
+
+        @config.add_cleanup
+        def cleanup_first():
+            report.append("cleanup_first")
+
+        with pytest.raises(MyError, match=r"raise_2"):
+            config._ensure_unconfigure()
+
+        assert report == ["cleanup_first", "raise_1", "raise_2", "cleanup_last"]
+
 
 class TestConfigFromdictargs:
     def test_basic_behavior(self, _sys_snapshot) -> None: