diff --git a/.gitea/workflows/cicd.yml b/.gitea/workflows/cicd.yml
index 7f1b936..048b90b 100644
--- a/.gitea/workflows/cicd.yml
+++ b/.gitea/workflows/cicd.yml
@@ -564,8 +564,9 @@ jobs:
               export CI=true &&
               export NODE_ENV=test &&
               echo 'Verifying Playwright installation...' &&
-              yarn playwright --version || echo 'Playwright CLI not available via yarn' &&
-              npx playwright --version || echo 'Playwright CLI not available via npx' &&
+              yarn playwright --version &&
+              echo 'Installing Playwright browser binaries...' &&
+              yarn playwright install --with-deps &&
               echo 'Running tests via yarn script...' &&
               yarn test:e2e --reporter=list
             else
diff --git a/Dockerfile.cicd b/Dockerfile.cicd
index a52a31c..ddae255 100644
--- a/Dockerfile.cicd
+++ b/Dockerfile.cicd
@@ -115,21 +115,26 @@ RUN export NODE_OPTIONS="--max-old-space-size=1024 --max-semi-space-size=64" &&
         echo "✓ Frontend dependencies installed (leveraging global tools)"; \
     fi
 
-# Playwright browsers are pre-installed in the base image for performance
-# Just verify they're available and compatible with project dependencies
+# Playwright browsers optimization check (may be pre-installed in base image)
 RUN if [ -f ".frontend-deps-failed" ]; then \
         echo "Frontend dependencies failed - Playwright E2E tests will be skipped"; \
     elif grep -q '@playwright/test' package.json && [ -d "node_modules" ]; then \
-        echo "Verifying Playwright browsers from base image..." && \
-        # Verify global Playwright CLI is working (installed via npm globally)
-        playwright --version && \
-        # Verify browsers are installed (they should be from base image)
-        playwright install --dry-run chromium firefox webkit || \
-        echo "Note: Using globally installed browsers from base image" && \
-        echo "✓ Playwright browsers available from base image"; \
+        echo "Checking Playwright browser optimization status..." && \
+        # Check if Playwright CLI is available via yarn (from project dependencies)
+        if yarn playwright --version >/dev/null 2>&1; then \
+            echo "✓ Playwright CLI available via yarn" && \
+            # Check if browsers are pre-installed from base image
+            if yarn playwright install --dry-run >/dev/null 2>&1; then \
+                echo "✓ Playwright browsers available from base image optimization"; \
+            else \
+                echo "⚠ Playwright browsers not pre-installed - will install on demand in CI"; \
+            fi; \
+        else \
+            echo "⚠ Playwright CLI not available - E2E setup will be handled in CI"; \
+        fi && \
+        echo "✓ Playwright environment checked"; \
     else \
-        echo "Playwright not found in package.json or node_modules missing"; \
-        echo "E2E tests will be skipped but browsers remain available from base image"; \
+        echo "ℹ No Playwright tests configured in this project"; \
     fi
 
 # Verify all tools are working with the project
diff --git a/docs/CICD_MULTI_STAGE_BUILD.md b/docs/CICD_MULTI_STAGE_BUILD.md
index e429598..a9c092b 100644
--- a/docs/CICD_MULTI_STAGE_BUILD.md
+++ b/docs/CICD_MULTI_STAGE_BUILD.md
@@ -184,6 +184,40 @@ RUN export NODE_OPTIONS="--max-old-space-size=1024" && \
 - **Memory Constraints**: Monitor swap usage on Raspberry Pi workers
 - **Network Timeouts**: Retry mechanisms handle transient failures
 
+#### Base Image Optimization Issues
+
+**Missing `/opt/python-dev-tools/` (Oct 2025 Resolution)**:
+- **Symptom**: Build fails with `No virtual environment or system Python installation found for path /opt/python-dev-tools/bin/python`
+- **Cause**: Base image in registry doesn't contain pre-installed Python dev tools optimization
+- **Fix Applied**: Made complete image resilient to missing optimization
+  ```dockerfile
+  # In Dockerfile.cicd - now handles missing pre-installed tools gracefully
+  if [ -f "/opt/python-dev-tools/bin/python" ]; then
+      echo "✓ Found pre-installed Python dev tools - leveraging cache"
+  else
+      echo "⚠ Pre-installed Python dev tools not found - fresh installation"
+  fi
+  ```
+- **Impact**: Builds continue successfully but without optimization benefits (~20s longer)
+- **Long-term Solution**: Rebuild base image to restore `/opt/python-dev-tools/` optimization
+
+**Playwright E2E Test Failures (Oct 2025 Resolution)**:
+- **Symptom**: `error: unknown option '--headed=false'` during E2E test execution
+- **Cause**: Invalid Playwright CLI flag syntax in workflow and documentation
+- **Fix Applied**:
+  - Removed invalid `--headed=false` flag (Playwright defaults to headless in CI)
+  - Changed to proper `yarn test:e2e --reporter=list` command
+  - Updated documentation with correct headless examples
+- **Key Learning**: Use yarn scripts (`yarn test:e2e`) rather than direct Playwright CLI calls
+
+**Missing Playwright Browser Binaries (Nov 2025 Resolution)**:
+- **Symptom**: `Executable doesn't exist at /root/.cache/ms-playwright/chromium_headless_shell-*/` for all browsers
+- **Cause**: Base image browsers not properly cached or registry image outdated
+- **Fix Applied**: Added `yarn playwright install --with-deps` step before running E2E tests in CI
+- **Docker Enhancement**: Made Dockerfile.cicd more resilient to missing browser optimization
+- **Impact**: E2E tests now work but download ~400MB of browsers each time (slower without base image optimization)
+- **Long-term Solution**: Rebuild base image to restore Playwright browser caching
+
 ## Migration Path
 
 ### From Single-Stage Build