diff --git a/nginx/entrypoint.sh b/nginx/entrypoint.sh
index 94be9d2..03b2f7e 100755
--- a/nginx/entrypoint.sh
+++ b/nginx/entrypoint.sh
@@ -47,6 +47,11 @@ else
 
     echo "Requesting Let's Encrypt certificate for ${DOMAIN}..."
 
+    # Clean stale certbot data from any previous failed attempt
+    rm -rf "/etc/letsencrypt/live/${DOMAIN}" \
+           "/etc/letsencrypt/archive/${DOMAIN}" \
+           "/etc/letsencrypt/renewal/${DOMAIN}.conf" 2>/dev/null || true
+
     # Attempt certificate acquisition
     if certbot certonly --webroot \
         -w /var/www/certbot \