diff --git a/.actions/pull_legacy_checkpoints.sh b/.actions/pull_legacy_checkpoints.sh
index cf8a0fdf4e574..b61647a96e50c 100644
--- a/.actions/pull_legacy_checkpoints.sh
+++ b/.actions/pull_legacy_checkpoints.sh
@@ -1,9 +1,11 @@
 #!/bin/bash
+
 # Run this script from the project root.
 URL="https://pl-public-data.s3.amazonaws.com/legacy/checkpoints.zip"
 mkdir -p tests/legacy
 # wget is simpler but does not work on Windows
 python -c "from urllib.request import urlretrieve; urlretrieve('$URL', 'tests/legacy/checkpoints.zip')"
 ls -l tests/legacy/
+
 unzip -o tests/legacy/checkpoints.zip -d tests/legacy/
 ls -l tests/legacy/checkpoints/
diff --git a/.azure/gpu-tests-pytorch.yml b/.azure/gpu-tests-pytorch.yml
index 4a381ffc16372..043909d793efd 100644
--- a/.azure/gpu-tests-pytorch.yml
+++ b/.azure/gpu-tests-pytorch.yml
@@ -123,13 +123,17 @@ jobs:
         python requirements/pytorch/check-avail-extras.py
       displayName: 'Env details'
 
-    - bash: bash .actions/pull_legacy_checkpoints.sh
-      displayName: 'Get legacy checkpoints'
-
     - bash: python -m pytest pytorch_lightning
       workingDirectory: src
       displayName: 'Testing: PyTorch doctests'
 
+    - bash: |
+        bash .actions/pull_legacy_checkpoints.sh
+        cd tests/legacy
+        bash generate_checkpoints.sh
+        ls -l checkpoints/
+      displayName: 'Get legacy checkpoints'
+
     - bash: python -m coverage run --source pytorch_lightning -m pytest --ignore benchmarks -v --junitxml=$(Build.StagingDirectory)/test-results.xml --durations=50
       env:
         PL_RUN_CUDA_TESTS: "1"
diff --git a/.github/workflows/ci-tests-pytorch.yml b/.github/workflows/ci-tests-pytorch.yml
index f0205930f0552..86dd0009aad89 100644
--- a/.github/workflows/ci-tests-pytorch.yml
+++ b/.github/workflows/ci-tests-pytorch.yml
@@ -98,10 +98,6 @@ jobs:
       if: ${{ matrix.requires == 'oldest' }}
       run: python .actions/assistant.py replace_oldest_ver
 
-    - name: Pull legacy checkpoints
-      if: ${{ matrix.type != 'slow' }}
-      run: bash .actions/pull_legacy_checkpoints.sh
-
     - name: Adjust PyTorch versions in requirements files
       if: ${{ matrix.requires != 'oldest' }}
       run: |
@@ -161,6 +157,14 @@ jobs:
           --source_import="pytorch_lightning,lightning_fabric" \
           --target_import="lightning.pytorch,lightning.fabric"
 
+    - name: Get legacy checkpoints
+      if: ${{ matrix.type != 'slow' }}
+      run: |
+        bash .actions/pull_legacy_checkpoints.sh
+        cd tests/legacy
+        bash generate_checkpoints.sh
+        ls -l checkpoints/
+
     - name: Testing Warnings
       # the stacklevel can only be set on >=3.7
       if: matrix.python-version != '3.7'
diff --git a/tests/legacy/back-compatible-versions.txt b/tests/legacy/back-compatible-versions.txt
index c2bc418eecd93..4dc21c75b39c0 100644
--- a/tests/legacy/back-compatible-versions.txt
+++ b/tests/legacy/back-compatible-versions.txt
@@ -77,3 +77,9 @@
 1.8.4
 1.8.5
 1.8.6
+1.9.0
+1.9.1
+1.9.2
+1.9.3
+1.9.4
+1.9.5
diff --git a/tests/legacy/generate_checkpoints.sh b/tests/legacy/generate_checkpoints.sh
index 7873daf3fe56f..3091d7948fca8 100644
--- a/tests/legacy/generate_checkpoints.sh
+++ b/tests/legacy/generate_checkpoints.sh
@@ -9,16 +9,17 @@ set -e
 LEGACY_PATH=$(cd $(dirname $0); pwd -P)
 ENV_PATH=$LEGACY_PATH/vEnv
 export PYTHONPATH=$(dirname $LEGACY_PATH)  # for `import tests_pytorch`
-echo LEGACY_PATH: $LEGACY_PATH
-echo ENV_PATH: $ENV_PATH
-echo PYTHONPATH: $PYTHONPATH
+printf "LEGACY_PATH: $LEGACY_PATH"
+printf "ENV_PATH: $ENV_PATH"
+printf "PYTHONPATH: $PYTHONPATH"
+rm -rf $ENV_PATH
 
 function create_and_save_checkpoint {
   python --version
   python -m pip --version
   python -m pip list
 
-  python $LEGACY_PATH/simple_classif_training.py
+  python $LEGACY_PATH/simple_classif_training.py $pl_ver
 
   cp $LEGACY_PATH/simple_classif_training.py $LEGACY_PATH/checkpoints/$pl_ver
   mv $LEGACY_PATH/checkpoints/$pl_ver/lightning_logs/version_0/checkpoints/*.ckpt $LEGACY_PATH/checkpoints/$pl_ver/
@@ -28,11 +29,9 @@ function create_and_save_checkpoint {
 # iterate over all arguments assuming that each argument is version
 for pl_ver in "$@"
 do
-  echo processing version: $pl_ver
+  printf "processing version: $pl_ver"
 
-  # Don't install/update anything before activating venv
-  # to avoid breaking any existing environment.
-  rm -rf $ENV_PATH
+  # Don't install/update anything before activating venv to avoid breaking any existing environment.
   python -m venv $ENV_PATH
   source $ENV_PATH/bin/activate
 
@@ -47,10 +46,9 @@ done
 
 # use the PL installed in the environment if no PL version is specified
 if [[ -z "$@" ]]; then
-  pl_ver=$(python -c "import pytorch_lightning as pl; print(pl.__version__)")
-  echo processing version: $pl_ver
+  printf "processing local version"
 
   python -m pip install -r $LEGACY_PATH/requirements.txt
-
+  pl_ver="local"
   create_and_save_checkpoint
 fi
diff --git a/tests/legacy/requirements.txt b/tests/legacy/requirements.txt
index fd2281e591624..43cd22c429f8b 100644
--- a/tests/legacy/requirements.txt
+++ b/tests/legacy/requirements.txt
@@ -1,2 +1,2 @@
-torchmetrics  # necessary because old PL verions don't have it as dependency
+torchmetrics  # necessary because old PL versions don't have it as dependency
 scikit-learn
diff --git a/tests/legacy/simple_classif_training.py b/tests/legacy/simple_classif_training.py
index 00e51627efad9..b4116ee6c5444 100644
--- a/tests/legacy/simple_classif_training.py
+++ b/tests/legacy/simple_classif_training.py
@@ -12,6 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 import os
+import sys
 
 import torch
 
@@ -50,5 +51,6 @@ def main_train(dir_path, max_epochs: int = 20):
 
 
 if __name__ == "__main__":
-    path_dir = os.path.join(PATH_LEGACY, "checkpoints", str(pl.__version__))
+    name = sys.argv[1] if len(sys.argv) > 1 else str(pl.__version__)
+    path_dir = os.path.join(PATH_LEGACY, "checkpoints", name)
     main_train(path_dir)
diff --git a/tests/tests_pytorch/checkpointing/test_legacy_checkpoints.py b/tests/tests_pytorch/checkpointing/test_legacy_checkpoints.py
index f00ca383d3149..f4781b66fd2e6 100644
--- a/tests/tests_pytorch/checkpointing/test_legacy_checkpoints.py
+++ b/tests/tests_pytorch/checkpointing/test_legacy_checkpoints.py
@@ -32,6 +32,8 @@
 # load list of all back compatible versions
 with open(os.path.join(_PATH_LEGACY, "back-compatible-versions.txt")) as fp:
     LEGACY_BACK_COMPATIBLE_PL_VERSIONS = [ln.strip() for ln in fp.readlines()]
+# This shall be created for each CI run
+LEGACY_BACK_COMPATIBLE_PL_VERSIONS += ["local"]
 
 
 @pytest.mark.parametrize("pl_version", LEGACY_BACK_COMPATIBLE_PL_VERSIONS)
diff --git a/tests/tests_pytorch/graveyard/test_legacy_import_unpickler.py b/tests/tests_pytorch/graveyard/test_legacy_import_unpickler.py
index 07a79dccd975b..3bfdc4b339c5a 100644
--- a/tests/tests_pytorch/graveyard/test_legacy_import_unpickler.py
+++ b/tests/tests_pytorch/graveyard/test_legacy_import_unpickler.py
@@ -58,7 +58,7 @@ def test_imports_unified(pl_version: str):
     path_ckpt = path_ckpts[-1]
 
     # only below version 1.5.0 we pickled stuff in checkpoints
-    if Version(pl_version) < Version("1.5.0"):
+    if pl_version != "local" and Version(pl_version) < Version("1.5.0"):
         context = pytest.warns(UserWarning, match="Redirecting import of")
     else:
         context = no_warning_call(match="Redirecting import of*")