diff --git a/.github/workflows/py-cli-e2e-tests.yml b/.github/workflows/py-cli-e2e-tests.yml
index a812d22b7a3..f2a747fcb47 100644
--- a/.github/workflows/py-cli-e2e-tests.yml
+++ b/.github/workflows/py-cli-e2e-tests.yml
@@ -57,13 +57,18 @@ jobs:
         make install_all install_test
 
     - name: Start Server and Ingest Sample Data
+      uses: nick-fields/retry@v2.8.3
       env:
         INGESTION_DEPENDENCY: "mysql,elasticsearch"
-      run: ./docker/run_local_docker.sh -m no-ui
-      timeout-minutes: 30
+      with:
+        timeout-minutes: 30
+        max_attempts: 2
+        retry_on: error
+        command: ./docker/run_local_docker.sh -m no-ui
 
     - name: Run Python Tests & record coverage
       if: matrix.e2e-test == 'python'
+      id: python-e2e-test
       run: |
         source env/bin/activate
         make coverage
@@ -99,15 +104,16 @@ jobs:
       run: |
         source env/bin/activate
         coverage run --rcfile ingestion/.coveragerc --data-file .coverage.$E2E_TEST -a --branch -m pytest -c ingestion/setup.cfg --junitxml=ingestion/junit/test-results-$E2E_TEST.xml --ignore=ingestion/tests/unit/source ingestion/tests/unit ingestion/tests/cli_e2e/test_cli_$E2E_TEST.py
+        coverage report --rcfile ingestion/.coveragerc --data-file .coverage.$E2E_TEST || true
 
-    - name: Upload coverage artifact
-      if: matrix.e2e-test == 'python' && steps.e2e-test.outcome == 'success'
+    - name: Upload coverage artifact for Python tests
+      if: matrix.e2e-test == 'python' && steps.python-e2e-test.outcome == 'success'
       uses: actions/upload-artifact@v3
       with:
         name: coverage-${{ matrix.e2e-test }}
         path: .coverage
 
-    - name: Upload coverage artifact for Python tests
+    - name: Upload coverage artifact for CLI E2E tests
       if: matrix.e2e-test != 'python' && steps.e2e-test.outcome == 'success'
       uses: actions/upload-artifact@v3
       with:
@@ -115,7 +121,7 @@ jobs:
         path: .coverage.${{ matrix.e2e-test }}
 
     - name: Upload tests artifact
-      if: steps.e2e-test.outcome == 'success'
+      if: steps.e2e-test.outcome == 'success' || steps.python-e2e-test.outcome == 'success'
       uses: actions/upload-artifact@v3
       with:
         name: tests-${{ matrix.e2e-test }}
@@ -128,7 +134,7 @@ jobs:
         sudo rm -rf ${PWD}/docker-volume
 
     - name: Slack on Failure
-      if: steps.e2e-test.outcome != 'success'
+      if: steps.e2e-test.outcome != 'success' || steps.python-e2e-test.outcome != 'success'
       uses: slackapi/slack-github-action@v1.23.0
       with:
         payload: |
@@ -140,7 +146,7 @@ jobs:
         SLACK_WEBHOOK_TYPE: INCOMING_WEBHOOK
 
     - name: Force failure
-      if: steps.e2e-test.outcome != 'success'
+      if: steps.e2e-test.outcome != 'success' || steps.python-e2e-test.outcome != 'success'
       run: |
         exit 1