diff --git a/CHANGELOG.md b/CHANGELOG.md
index bab85ad73..747d3c794 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -24,6 +24,7 @@ Docs: https://docs.openclaw.ai
 - Plugins/SDK subpath parity: add channel-specific plugin SDK subpaths for Discord, Slack, Signal, iMessage, WhatsApp, and LINE; migrate bundled plugin entrypoints to scoped subpaths/core with CI guardrails; and keep `openclaw/plugin-sdk` root import compatibility for existing external plugins. (#33737) thanks @gumadeiras.
 - Routing/session duplicate suppression synthesis: align shared session delivery-context inheritance, channel-paired route-field merges, and reply-surface target matching so dmScope=main turns avoid cross-surface duplicate replies while thread-aware forwarding keeps intended routing semantics. (from #33629, #26889, #17337, #33250) Thanks @Yuandiaodiaodiao, @kevinwildenradt, @Glucksberg, and @bmendonca3.
 - Routing/legacy session route inheritance: preserve external route metadata inheritance for legacy channel session keys (`agent:<agent>:<channel>:<peer>` and `...:thread:<id>`) so `chat.send` does not incorrectly fall back to webchat when valid delivery context exists. Follow-up to #33786.
+- Routing/legacy route guard tightening: require legacy session-key channel hints to match the saved delivery channel before inheriting external routing metadata, preventing custom namespaced keys like `agent:<agent>:work:<ticket>` from inheriting stale non-webchat routes.
 - Security/auth labels: remove token and API-key snippets from user-facing auth status labels so `/status` and `/models` do not expose credential fragments. (#33262) thanks @cu1ch3n.
 - Auth/credential semantics: align profile eligibility + probe diagnostics with SecretRef/expiry rules and harden browser download atomic writes. (#33733) thanks @joshavant.
 - Security/audit denyCommands guidance: suggest likely exact node command IDs for unknown `gateway.nodes.denyCommands` entries so ineffective denylist entries are easier to correct. (#29713) thanks @liquidhorizon88-bot.
diff --git a/src/gateway/server-methods/chat.directive-tags.test.ts b/src/gateway/server-methods/chat.directive-tags.test.ts
index b6f6fce38..0ea0e0181 100644
--- a/src/gateway/server-methods/chat.directive-tags.test.ts
+++ b/src/gateway/server-methods/chat.directive-tags.test.ts
@@ -570,7 +570,9 @@ describe("chat directive tag stripping for non-streaming final payloads", () =>
       context,
       respond,
       idempotencyKey: "idem-custom-no-cross-route",
-      sessionKey: "agent:main:work",
+      // Keep a second custom scope token so legacy-shape detection is exercised.
+      // "agent:main:work" only yields one rest token and does not hit that path.
+      sessionKey: "agent:main:work:ticket-123",
       expectBroadcast: false,
     });
 
diff --git a/src/gateway/server-methods/chat.ts b/src/gateway/server-methods/chat.ts
index 7c8db7344..db78d7966 100644
--- a/src/gateway/server-methods/chat.ts
+++ b/src/gateway/server-methods/chat.ts
@@ -876,7 +876,9 @@ export const chatHandlers: GatewayRequestHandlers = {
         CHANNEL_SCOPED_SESSION_SHAPES.has(part),
       );
       const hasLegacyChannelPeerShape =
-        !isChannelScopedSession && typeof sessionScopeParts[1] === "string";
+        !isChannelScopedSession &&
+        typeof sessionScopeParts[1] === "string" &&
+        sessionChannelHint === routeChannelCandidate;
       // Only inherit prior external route metadata for channel-scoped sessions.
       // Channel-agnostic sessions (main, direct:<peer>, etc.) can otherwise
       // leak stale routes across surfaces.