diff --git a/src/commands/configure.gateway.ts b/src/commands/configure.gateway.ts
index 9b66a7b34..c83c8d2a0 100644
--- a/src/commands/configure.gateway.ts
+++ b/src/commands/configure.gateway.ts
@@ -177,7 +177,8 @@ export async function promptGatewayConfig(
       }),
       runtime,
     );
-    gatewayToken = String(tokenInput).trim() || randomToken();
+    const rawInput = tokenInput ? String(tokenInput).trim() : "";
+    gatewayToken = rawInput || randomToken();
   }
 
   if (authMode === "password") {
diff --git a/src/wizard/onboarding.gateway-config.ts b/src/wizard/onboarding.gateway-config.ts
index d7dceae24..b5eb00829 100644
--- a/src/wizard/onboarding.gateway-config.ts
+++ b/src/wizard/onboarding.gateway-config.ts
@@ -182,7 +182,9 @@ export async function configureGatewayForOnboarding(
         placeholder: "Needed for multi-machine or non-loopback access",
         initialValue: quickstartGateway.token ?? "",
       });
-      gatewayToken = String(tokenInput).trim() || randomToken();
+      // FIX: Ensure undefined becomes an empty string, not "undefined" string
+      const rawInput = tokenInput ? String(tokenInput).trim() : "";
+      gatewayToken = rawInput || randomToken();
     }
   }