diff --git a/.github/workflows/osgeo4w.yml b/.github/workflows/osgeo4w.yml
index cfa02d9472e..6f4e35d8499 100644
--- a/.github/workflows/osgeo4w.yml
+++ b/.github/workflows/osgeo4w.yml
@@ -127,15 +127,51 @@ jobs:
         run: |
           python -m pip install ^
             pytest ^
+            pytest-randomly ^
             pytest-timeout
         shell: cmd /D /E:ON /V:OFF /S /C "CALL C:/OSGeo4W/OSGeo4W.bat "{0}""
-      - name: Run pytest with a single worker
+      - name: Run pytest with a single worker I
+        continue-on-error: true
         run: |
           call %OSGEO4W_ROOT%\opt\grass\etc\env.bat
           set PYTHONPATH=%GISBASE%\etc\python;%PYTHONPATH%
           path %GISBASE%\lib;%GISBASE%\bin;%PATH%
           pytest ^
             @.github/workflows/pytest_args_ci.txt ^
+            --maxfail=10 ^
+            -k "not testsuite"
+        shell: cmd /D /E:ON /V:OFF /S /C "CALL C:/OSGeo4W/OSGeo4W.bat "{0}""
+      - name: Run pytest with a single worker II
+        continue-on-error: true
+        run: |
+          call %OSGEO4W_ROOT%\opt\grass\etc\env.bat
+          set PYTHONPATH=%GISBASE%\etc\python;%PYTHONPATH%
+          path %GISBASE%\lib;%GISBASE%\bin;%PATH%
+          pytest ^
+            @.github/workflows/pytest_args_ci.txt ^
+            --maxfail=10 ^
+            -k "not testsuite"
+        shell: cmd /D /E:ON /V:OFF /S /C "CALL C:/OSGeo4W/OSGeo4W.bat "{0}""
+      - name: Run pytest with a single worker III
+        continue-on-error: true
+        run: |
+          call %OSGEO4W_ROOT%\opt\grass\etc\env.bat
+          set PYTHONPATH=%GISBASE%\etc\python;%PYTHONPATH%
+          path %GISBASE%\lib;%GISBASE%\bin;%PATH%
+          pytest ^
+            @.github/workflows/pytest_args_ci.txt ^
+            --maxfail=10 ^
+            -k "not testsuite"
+        shell: cmd /D /E:ON /V:OFF /S /C "CALL C:/OSGeo4W/OSGeo4W.bat "{0}""
+      - name: Run pytest with a single worker IV
+        continue-on-error: true
+        run: |
+          call %OSGEO4W_ROOT%\opt\grass\etc\env.bat
+          set PYTHONPATH=%GISBASE%\etc\python;%PYTHONPATH%
+          path %GISBASE%\lib;%GISBASE%\bin;%PATH%
+          pytest ^
+            @.github/workflows/pytest_args_ci.txt ^
+            --maxfail=10 ^
             -k "not testsuite"
         shell: cmd /D /E:ON /V:OFF /S /C "CALL C:/OSGeo4W/OSGeo4W.bat "{0}""
       - name: Run pytest with a single worker (for gunittest-based tests)
diff --git a/python/grass/script/setup.py b/python/grass/script/setup.py
index 8baf3cc7956..2010d682379 100644
--- a/python/grass/script/setup.py
+++ b/python/grass/script/setup.py
@@ -236,6 +236,23 @@ def setup_runtime_env(gisbase=None, *, env=None):
     )
     set_python_path_variable(install_path=gisbase, env=env)
     set_path_to_python_executable(env=env)
+    if sys.platform.startswith("win32"):
+        # pylint: disable=import-outside-toplevel
+        from .core import start_command, PIPE, create_environment
+        from .utils import try_remove
+
+        # On Windows, first call to an executable fails, but the following ones work.
+        # Let's do the first call here and ignore the result.
+        # While g.message does not theoretically need a project, g.gisenv is called for
+        # debug level which is stored in gisrc.
+        gisrc, full_env = create_environment(
+            "test_db", "test_project", "test_mapset", env=env
+        )
+        process = start_command(
+            "g.message", message="test", stdout=PIPE, stderr=PIPE, env=full_env
+        )
+        unused_stdout, unused_stderr = process.communicate()
+        try_remove(gisrc)
 
 
 def runtime_env_is_active(env=None):