diff --git a/docker-compose.coolify.yaml b/docker-compose.coolify.yaml
index ba1cbb752..6b4445dee 100644
--- a/docker-compose.coolify.yaml
+++ b/docker-compose.coolify.yaml
@@ -46,7 +46,7 @@ services:
       - command:
         - sh
         - '-c'
-        - 'bundle exec rails db:chatwoot_prepare && bundle exec rails branding:update && if [ -n "$${BRAND_ASSETS_URL}" ]; then deployment/extract_brand_assets.sh "$${BRAND_ASSETS_URL}"; fi'
+        - 'bundle exec rails branding:update && if [ -n "$${BRAND_ASSETS_URL}" ]; then deployment/extract_brand_assets.sh "$${BRAND_ASSETS_URL}"; fi'
     healthcheck:
       test:
         - CMD-SHELL
@@ -61,8 +61,12 @@ services:
     volumes:
       - 'storage:/app/storage'
     depends_on:
-      - postgres
-      - redis
+      rails:
+        condition: service_healthy
+      postgres:
+        condition: service_started
+      redis:
+        condition: service_started
     environment:
       - NODE_ENV=production
       - RAILS_ENV=production
diff --git a/docker/entrypoints/rails.sh b/docker/entrypoints/rails.sh
index 77657f6ee..bd17c7f25 100755
--- a/docker/entrypoints/rails.sh
+++ b/docker/entrypoints/rails.sh
@@ -30,5 +30,11 @@ do
   sleep 2;
 done
 
+# Run pending migrations before starting the server so that workers
+# (sidekiq) that depend on the rails healthcheck never see a stale schema.
+echo "Running db:chatwoot_prepare..."
+bundle exec rake db:chatwoot_prepare
+echo "Database preparation complete."
+
 # Execute the main process of the container
 exec "$@"