diff --git a/Dockerfile b/Dockerfile
index b1936099e8..18fed7b57f 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -8,7 +8,39 @@ FROM espocrm/espocrm:latest
 # Copy custom extensions and modifications
 COPY custom/ /var/www/html/custom/
 
-# Ensure correct permissions for custom dir
+# Ensure correct permissions
 RUN chown -R www-data:www-data /var/www/html/custom
 
+# Post-deploy: clear cache and rebuild on startup
+COPY --chmod=755 <<'EOF' /usr/local/bin/post-deploy.sh
+#!/bin/bash
+set -e
+
+# Wait for the original entrypoint to finish setup
+sleep 5
+
+# Clear cache so EspoCRM picks up new/changed extensions
+if [ -d "/var/www/html/data/cache" ]; then
+    rm -rf /var/www/html/data/cache/*
+    echo "Cache cleared."
+fi
+
+# Run rebuild if config exists (means EspoCRM is installed)
+if [ -f "/var/www/html/data/config.php" ]; then
+    cd /var/www/html
+    php rebuild.php
+    echo "Rebuild complete."
+fi
+EOF
+
+# Wrap the original entrypoint to run post-deploy after startup
+COPY --chmod=755 <<'EOF' /usr/local/bin/dev-entrypoint.sh
+#!/bin/bash
+# Run post-deploy in background after container starts
+(post-deploy.sh &)
+# Execute original entrypoint
+exec docker-entrypoint.sh apache2-foreground
+EOF
+
 EXPOSE 80
+ENTRYPOINT ["dev-entrypoint.sh"]