diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index b071e7e4e3..1e2b6d2777 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -34,15 +34,15 @@ jobs:
           - { python-version: "3.9",  tox-env: type-checking }
           - { python-version: "3.10", tox-env: type-checking }
           - { python-version: "3.11", tox-env: type-checking }
-          - { python-version: "3.8",  tox-env: py38,          max-attempts: 3 }
-          - { python-version: "3.8",  tox-env: py38-no-ext,   max-attempts: 3 }
+          - { python-version: "3.8",  tox-env: py38,          max-attempts: 1, timeout-minutes: 20}
+          - { python-version: "3.8",  tox-env: py38-no-ext,   max-attempts: 1, timeout-minutes: 20}
           - { python-version: "3.9",  tox-env: py39,          max-attempts: 3 }
           - { python-version: "3.9",  tox-env: py39-no-ext,   max-attempts: 3 }
           - { python-version: "3.10", tox-env: py310,         max-attempts: 3 }
           - { python-version: "3.10", tox-env: py310-no-ext,  max-attempts: 3 }
           - { python-version: "3.11", tox-env: py311,         max-attempts: 3 }
           - { python-version: "3.11", tox-env: py311-no-ext,  max-attempts: 3 }
-          - { python-version: "3.8",  tox-env: py38-no-ext,   platform: windows-latest, ignore-errors: true }
+          - { python-version: "3.8",  tox-env: py38-no-ext,   platform: windows-latest, ignore-errors: true, timeout-minutes: 20 }
           - { python-version: "3.9",  tox-env: py39-no-ext,   platform: windows-latest, ignore-errors: true }
           - { python-version: "3.10", tox-env: py310-no-ext,  platform: windows-latest, ignore-errors: true }
           - { python-version: "3.11", tox-env: py310-no-ext,  platform: windows-latest, ignore-errors: true }
@@ -54,3 +54,4 @@ jobs:
           tox-env: ${{ matrix.config.tox-env }}
           max-attempts: ${{ matrix.config.max-attempts || 1 }}
           ignore-errors: ${{ matrix.config.ignore-errors || false }}
+          timeout-minutes: ${{ matrix.config.timeout-minutes || 15 }}
diff --git a/tests/typing/test_typing.py b/tests/typing/test_typing.py
index bdb7bf5643..7ba11b2ad7 100644
--- a/tests/typing/test_typing.py
+++ b/tests/typing/test_typing.py
@@ -111,7 +111,7 @@ def test_check_app_default(
                 assert note in output, output
             except AssertionError:
                 target = target.parent
-                if not target.exists():
+                if not target.exists() or target == target.parent:
                     raise
             else:
                 break