diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index c41f013..5fb2303 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -11,6 +11,18 @@ jobs:
       - name: Checkout
         uses: actions/checkout@v4
 
+      # The test image below swaps in Caddyfile.test, so the production
+      # Caddyfile is otherwise never exercised by CI — an invalid config then
+      # only surfaces when the deploy health-gate fails, after the broken
+      # container already replaced the healthy one (issue #20/#26). Validate
+      # both files up front so a parse error fails the PR check in seconds.
+      - name: Validate Caddyfiles
+        run: |
+          docker run --rm -v "$PWD":/workspace -w /workspace caddy:2-alpine \
+            caddy validate --config Caddyfile --adapter caddyfile
+          docker run --rm -v "$PWD":/workspace -w /workspace caddy:2-alpine \
+            caddy validate --config Caddyfile.test --adapter caddyfile
+
       - name: Build Docker image
         run: docker build -t learning-platform .