diff --git a/src/gateway/server/ws-connection/message-handler.ts b/src/gateway/server/ws-connection/message-handler.ts
index d1f6ae511..c67dd5ab0 100644
--- a/src/gateway/server/ws-connection/message-handler.ts
+++ b/src/gateway/server/ws-connection/message-handler.ts
@@ -634,7 +634,7 @@ export function attachGatewayWsMessageHandler(params: {
               role,
               scopes,
               remoteIp: reportedClientIp,
-              silent: isLocalClient,
+              silent: isLocalClient || authMethod === "tailscale",
             });
             const context = buildRequestContext();
             if (pairing.request.silent === true) {