diff --git a/src/shadowbox/server/manager_service.ts b/src/shadowbox/server/manager_service.ts
index 84fef7fd..7791b4db 100644
--- a/src/shadowbox/server/manager_service.ts
+++ b/src/shadowbox/server/manager_service.ts
@@ -393,7 +393,10 @@ export class ShadowsocksManagerService {
         const domain = configData?.caddyWebServer?.domain || configData?.hostname;
         const listenersConfig = configData?.listenersForNewAccessKeys;
         
-        if (domain && listenersConfig) {
+        logging.debug(`WebSocket key detected. Domain: ${domain}, Listeners config: ${JSON.stringify(listenersConfig)}`);
+        
+        // Generate YAML even if listenersConfig is not fully configured, using defaults
+        if (domain) {
           const serverWithWebSocket = this.shadowsocksServer as ShadowsocksServer & {
             generateDynamicAccessKeyYaml?: (
               proxyParams: {encryptionMethod: string; password: string},
@@ -407,8 +410,8 @@ export class ShadowsocksManagerService {
           const yamlConfig = serverWithWebSocket.generateDynamicAccessKeyYaml?.(
             accessKey.proxyParams,
             domain,
-            listenersConfig.websocketStream?.path || '/tcp',
-            listenersConfig.websocketPacket?.path || '/udp',
+            listenersConfig?.websocketStream?.path || '/tcp',
+            listenersConfig?.websocketPacket?.path || '/udp',
             this.serverConfig.data()?.caddyWebServer?.autoHttps !== false
           );
           
diff --git a/src/shadowbox/server/outline_shadowsocks_server.ts b/src/shadowbox/server/outline_shadowsocks_server.ts
index d8157a06..5c538f45 100644
--- a/src/shadowbox/server/outline_shadowsocks_server.ts
+++ b/src/shadowbox/server/outline_shadowsocks_server.ts
@@ -298,22 +298,23 @@ export class OutlineShadowsocksServer implements ShadowsocksServer {
 
     const protocol = tls ? 'wss' : 'ws';
     
+    // Generate YAML configuration matching Outline client spec exactly
     const config = {
       transport: {
-        $type: 'tcpudp',
+        '$type': 'tcpudp',
         tcp: {
-          $type: 'shadowsocks',
+          '$type': 'shadowsocks',
           endpoint: {
-            $type: 'websocket',
+            '$type': 'websocket',
             url: `${protocol}://${domain}${tcpPath}`
           },
           cipher: proxyParams.encryptionMethod,
           secret: proxyParams.password
         },
         udp: {
-          $type: 'shadowsocks',
+          '$type': 'shadowsocks',
           endpoint: {
-            $type: 'websocket',
+            '$type': 'websocket',
             url: `${protocol}://${domain}${udpPath}`
           },
           cipher: proxyParams.encryptionMethod,
@@ -322,7 +323,15 @@ export class OutlineShadowsocksServer implements ShadowsocksServer {
       }
     };
 
-    return jsyaml.safeDump(config, {sortKeys: true});
+    // Use specific YAML options to ensure proper formatting
+    return jsyaml.dump(config, {
+      indent: 2,
+      lineWidth: -1,  // Don't wrap long lines
+      noRefs: true,   // Don't use references
+      sortKeys: false, // Preserve key order
+      quotingType: '"', // Use double quotes when needed
+      forceQuotes: false // Don't quote all strings
+    });
   }
 
   private start() {