diff --git a/src/poetry/core/utils/helpers.py b/src/poetry/core/utils/helpers.py
index aa5354feb..d9127831b 100644
--- a/src/poetry/core/utils/helpers.py
+++ b/src/poetry/core/utils/helpers.py
@@ -37,8 +37,10 @@ def temporary_directory(*args: Any, **kwargs: Any) -> Iterator[Path]:
             yield Path(name)
     else:
         name = tempfile.mkdtemp(*args, **kwargs)
-        yield Path(name)
-        robust_rmtree(name)
+        try:
+            yield Path(name)
+        finally:
+            robust_rmtree(name)
 
 
 def parse_requires(requires: str) -> list[str]:
diff --git a/tests/utils/test_helpers.py b/tests/utils/test_helpers.py
index fbdde65ce..6de9c20cf 100644
--- a/tests/utils/test_helpers.py
+++ b/tests/utils/test_helpers.py
@@ -127,6 +127,7 @@ def test_utils_helpers_readme_content_type(
     assert readme_content_type(readme) == content_type
 
 
+@pytest.mark.skipif(sys.version_info < (3, 10), reason="Requires Python 3.10 or higher")
 def test_temporary_directory_python_3_10_or_newer(mocker: MockerFixture) -> None:
     mocked_rmtree = mocker.patch("shutil.rmtree")
     mocked_temp_dir = mocker.patch("tempfile.TemporaryDirectory")
@@ -134,7 +135,6 @@ def test_temporary_directory_python_3_10_or_newer(mocker: MockerFixture) -> None
 
     mocked_temp_dir.return_value.__enter__.return_value = "hello from test"
 
-    mocker.patch.object(sys, "version_info", (3, 10))
     with temporary_directory() as tmp:
         assert tmp == Path("hello from test")
 
@@ -143,6 +143,31 @@ def test_temporary_directory_python_3_10_or_newer(mocker: MockerFixture) -> None
     mocked_temp_dir.assert_called_with(ignore_cleanup_errors=True)
 
 
+@pytest.mark.skipif(sys.version_info < (3, 10), reason="Requires Python 3.10 or higher")
+def test_temporary_directory_python_3_10_or_newer_ensure_cleanup_on_error(
+    mocker: MockerFixture,
+) -> None:
+    mocked_rmtree = mocker.patch("shutil.rmtree")
+    mocked_temp_dir = mocker.patch("tempfile.TemporaryDirectory")
+    mocked_mkdtemp = mocker.patch("tempfile.mkdtemp")
+
+    mocked_temp_dir.return_value.__enter__.return_value = "hello from test"
+
+    with pytest.raises(
+        Exception, match="Something went wrong"
+    ), temporary_directory() as tmp:
+        assert tmp == Path("hello from test")
+
+        raise Exception("Something went wrong")
+
+    assert not mocked_rmtree.called
+    assert not mocked_mkdtemp.called
+    mocked_temp_dir.assert_called_with(ignore_cleanup_errors=True)
+
+
+@pytest.mark.skipif(
+    sys.version_info >= (3, 10), reason="Not supported on Python 3.10 or higher"
+)
 def test_temporary_directory_python_3_9_or_older(mocker: MockerFixture) -> None:
     mocked_rmtree = mocker.patch("shutil.rmtree")
     mocked_temp_dir = mocker.patch("tempfile.TemporaryDirectory")
@@ -150,7 +175,6 @@ def test_temporary_directory_python_3_9_or_older(mocker: MockerFixture) -> None:
 
     mocked_mkdtemp.return_value = "hello from test"
 
-    mocker.patch.object(sys, "version_info", (3, 9))
     with temporary_directory() as tmp:
         assert tmp == Path("hello from test")
 
@@ -159,6 +183,30 @@ def test_temporary_directory_python_3_9_or_older(mocker: MockerFixture) -> None:
     assert not mocked_temp_dir.called
 
 
+@pytest.mark.skipif(
+    sys.version_info >= (3, 10), reason="Not supported on Python 3.10 or higher"
+)
+def test_temporary_directory_python_3_9_or_older_ensure_cleanup_on_error(
+    mocker: MockerFixture,
+) -> None:
+    mocked_rmtree = mocker.patch("shutil.rmtree")
+    mocked_temp_dir = mocker.patch("tempfile.TemporaryDirectory")
+    mocked_mkdtemp = mocker.patch("tempfile.mkdtemp")
+
+    mocked_mkdtemp.return_value = "hello from test"
+
+    with pytest.raises(
+        Exception, match="Something went wrong"
+    ), temporary_directory() as tmp:
+        assert tmp == Path("hello from test")
+
+        raise Exception("Something went wrong")
+
+    assert mocked_rmtree.called
+    assert mocked_mkdtemp.called
+    assert not mocked_temp_dir.called
+
+
 def test_robust_rmtree(mocker: MockerFixture) -> None:
     mocked_rmtree = mocker.patch("shutil.rmtree")