diff --git a/src/services/webhook-manager.ts b/src/services/webhook-manager.ts
index a39ba7c..aad54a7 100644
--- a/src/services/webhook-manager.ts
+++ b/src/services/webhook-manager.ts
@@ -43,6 +43,23 @@ export class WebhookManager {
 
 		try {
 			const url = new URL(process.env.WEBHOOK_URL);
+			
+			// Enhanced internal Docker URL validation
+			if (process.env.WEBHOOK_URL.startsWith('http://srv-captain--')) {
+				if (!url.port) {
+					console.warn('⚠️ Internal Docker URL missing port number - this may cause connection issues');
+					// Auto-fix for common CapRover default port
+					if (process.env.PORT) {
+						process.env.WEBHOOK_URL = process.env.WEBHOOK_URL.replace(
+							'http://srv-captain--',
+							`http://srv-captain--:${process.env.PORT}/`
+						);
+						console.warn(`⚠️ Auto-corrected URL to: ${process.env.WEBHOOK_URL.substring(0, 30)}...`);
+						return; // Skip further validation for corrected URL
+					}
+				}
+			}
+			
 			// Allow internal docker URLs in production
 			if (process.env.NODE_ENV === 'production') {
 				if (!['http:', 'https:', 'http://srv-captain--'].some(prefix =>