diff --git a/.github/workflows/docker-build.yml b/.github/workflows/docker-build.yml
index 46289859..a3f4ddee 100644
--- a/.github/workflows/docker-build.yml
+++ b/.github/workflows/docker-build.yml
@@ -100,8 +100,8 @@ jobs:
         if: steps.skip.outputs.skip_build != 'true'
         id: caddy
         run: |
-          docker pull debian:bookworm-slim
-          DIGEST=$(docker inspect --format='{{index .RepoDigests 0}}' debian:bookworm-slim)
+          docker pull debian:trixie-slim
+          DIGEST=$(docker inspect --format='{{index .RepoDigests 0}}' debian:trixie-slim)
           echo "image=$DIGEST" >> $GITHUB_OUTPUT
 
       - name: Log in to Container Registry
@@ -478,7 +478,7 @@ jobs:
 
           # Wait for container to be healthy (max 3 minutes - Debian needs more startup time)
           echo "Waiting for container to start..."
-          timeout 180s bash -c 'until docker exec test-container curl -q -O- http://localhost:8080/api/v1/health 2>/dev/null | grep -q "status"; do echo "Waiting..."; sleep 2; done' || {
+          timeout 180s bash -c 'until docker exec test-container curl -sf http://localhost:8080/api/v1/health 2>/dev/null | grep -q "status"; do echo "Waiting..."; sleep 2; done' || {
             echo "❌ Container failed to become healthy"
             docker logs test-container
             exit 1
diff --git a/docs/plans/merge-resolution-plan.md b/docs/plans/merge-resolution-plan.md
index 61cf5e7e..ea63dc66 100644
--- a/docs/plans/merge-resolution-plan.md
+++ b/docs/plans/merge-resolution-plan.md
@@ -7,6 +7,31 @@
 
 ---
 
+## 🔴 Workflow Failure Analysis (Added 2026-01-25)
+
+### Issue Identified: docker-build.yml Failure
+
+**Workflow Run**: https://github.com/Wikid82/Charon/actions/runs/21326638353
+
+**Root Cause**: Base image mismatch after Debian Trixie migration (PR #550)
+
+| Component | Before Fix | After Fix |
+|-----------|-----------|-----------|
+| Workflow `docker-build.yml` | `debian:bookworm-slim` | `debian:trixie-slim` |
+| Dockerfile `CADDY_IMAGE` | `debian:trixie-slim` | `debian:trixie-slim` ✓ |
+
+**Problem**: The workflow step "Resolve Debian base image digest" was still pulling `debian:bookworm-slim` while the Dockerfile was updated to use `debian:trixie-slim`. This caused inconsistency in the build.
+
+**Fix Applied**: Updated [.github/workflows/docker-build.yml](.github/workflows/docker-build.yml#L54-L57):
+```yaml
+- name: Resolve Debian base image digest
+  run: |
+    docker pull debian:trixie-slim
+    DIGEST=$(docker inspect --format='{{index .RepoDigests 0}}' debian:trixie-slim)
+```
+
+---
+
 ## Summary
 
 This plan addresses merge conflicts in the `feature/beta-release` branch that need resolution against `main`. After analyzing all conflicting files, here is the recommended resolution strategy.