diff --git a/src/agents/tools/gateway.test.ts b/src/agents/tools/gateway.test.ts
index 8f12e33c462..9f0d16eb361 100644
--- a/src/agents/tools/gateway.test.ts
+++ b/src/agents/tools/gateway.test.ts
@@ -75,6 +75,15 @@ describe("resolveGatewayTarget – env URL override classification", () => {
     expect(resolveGatewayTarget()).toBeUndefined();
   });
 
+  it("returns undefined (local) when gateway.mode=remote with a loopback remote.url (no tunnel evidence)", () => {
+    // A configured loopback remote.url (e.g. ws://127.0.0.1:18789) is indistinguishable
+    // from a local gateway on a custom port. Without a non-loopback URL proving SSH tunnel
+    // usage, classify as local so deliveryContext is preserved and post-restart wake
+    // messages are not misrouted via stale extractDeliveryInfo routing.
+    setConfig({ gateway: { mode: "remote", remote: { url: "ws://127.0.0.1:18789" } } });
+    expect(resolveGatewayTarget()).toBeUndefined();
+  });
+
   it("returns undefined when gateway.mode=remote but gateway.remote.url is empty string", () => {
     setConfig({ gateway: { mode: "remote", remote: { url: "  " } } });
     expect(resolveGatewayTarget()).toBeUndefined();
diff --git a/src/agents/tools/gateway.ts b/src/agents/tools/gateway.ts
index 84aa6101f40..613f57343e3 100644
--- a/src/agents/tools/gateway.ts
+++ b/src/agents/tools/gateway.ts
@@ -226,12 +226,12 @@ export function resolveGatewayTarget(opts?: GatewayCallOptions): GatewayOverride
         }
       }
     }
-    // No env override. When mode=remote with a configured remote URL → truly remote.
-    // When mode=remote but remote.url is absent, callGateway falls back to local loopback —
-    // classify that as local (undefined) so deliveryContext is not suppressed.
-    const remoteUrl =
-      cfg.gateway?.mode === "remote" ? trimToUndefined(cfg.gateway?.remote?.url) : undefined;
-    return cfg.gateway?.mode === "remote" && remoteUrl !== undefined ? "remote" : undefined;
+    // No env override. Classify as "remote" only when mode=remote is configured with a
+    // non-loopback remote URL. Loopback remote.url (e.g. ws://127.0.0.1:18789) is
+    // indistinguishable from a local gateway on a custom port; without a non-loopback
+    // URL proving SSH tunnel usage, treat it as local so deliveryContext is preserved
+    // and post-restart wake messages are not misrouted.
+    return isNonLoopbackRemoteUrlConfigured(cfg) ? "remote" : undefined;
   }
   return validateGatewayUrlOverrideForAgentTools({
     cfg,