diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5fe720c79..55dacd73e 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -22,6 +22,7 @@ Docs: https://docs.openclaw.ai
 - Config/heartbeat legacy-path handling: auto-migrate top-level `heartbeat` into `agents.defaults.heartbeat` (with merge semantics that preserve explicit defaults), and keep startup failures on non-migratable legacy entries in the detailed invalid-config path instead of generic migration-failed errors. (#32706) thanks @xiwan.
 - 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.
 - 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 4ab6875ff..b6f6fce38 100644
--- a/src/gateway/server-methods/chat.directive-tags.test.ts
+++ b/src/gateway/server-methods/chat.directive-tags.test.ts
@@ -448,6 +448,75 @@ describe("chat directive tag stripping for non-streaming final payloads", () =>
     );
   });
 
+  it("chat.send inherits routing metadata for legacy channel-peer session keys", async () => {
+    createTranscriptFixture("openclaw-chat-send-legacy-channel-peer-routing-");
+    mockState.finalText = "ok";
+    mockState.sessionEntry = {
+      deliveryContext: {
+        channel: "telegram",
+        to: "telegram:6812765697",
+        accountId: "default",
+      },
+      lastChannel: "telegram",
+      lastTo: "telegram:6812765697",
+      lastAccountId: "default",
+    };
+    const respond = vi.fn();
+    const context = createChatContext();
+
+    await runNonStreamingChatSend({
+      context,
+      respond,
+      idempotencyKey: "idem-legacy-channel-peer-routing",
+      sessionKey: "agent:main:telegram:6812765697",
+      expectBroadcast: false,
+    });
+
+    expect(mockState.lastDispatchCtx).toEqual(
+      expect.objectContaining({
+        OriginatingChannel: "telegram",
+        OriginatingTo: "telegram:6812765697",
+        AccountId: "default",
+      }),
+    );
+  });
+
+  it("chat.send inherits routing metadata for legacy channel-peer thread session keys", async () => {
+    createTranscriptFixture("openclaw-chat-send-legacy-thread-channel-peer-routing-");
+    mockState.finalText = "ok";
+    mockState.sessionEntry = {
+      deliveryContext: {
+        channel: "telegram",
+        to: "telegram:6812765697",
+        accountId: "default",
+        threadId: "42",
+      },
+      lastChannel: "telegram",
+      lastTo: "telegram:6812765697",
+      lastAccountId: "default",
+      lastThreadId: "42",
+    };
+    const respond = vi.fn();
+    const context = createChatContext();
+
+    await runNonStreamingChatSend({
+      context,
+      respond,
+      idempotencyKey: "idem-legacy-thread-channel-peer-routing",
+      sessionKey: "agent:main:telegram:6812765697:thread:42",
+      expectBroadcast: false,
+    });
+
+    expect(mockState.lastDispatchCtx).toEqual(
+      expect.objectContaining({
+        OriginatingChannel: "telegram",
+        OriginatingTo: "telegram:6812765697",
+        AccountId: "default",
+        MessageThreadId: "42",
+      }),
+    );
+  });
+
   it("chat.send does not inherit external delivery context for shared main sessions", async () => {
     createTranscriptFixture("openclaw-chat-send-main-no-cross-route-");
     mockState.finalText = "ok";
diff --git a/src/gateway/server-methods/chat.ts b/src/gateway/server-methods/chat.ts
index 382a39a8e..7c8db7344 100644
--- a/src/gateway/server-methods/chat.ts
+++ b/src/gateway/server-methods/chat.ts
@@ -875,6 +875,8 @@ export const chatHandlers: GatewayRequestHandlers = {
       const isChannelScopedSession = sessionPeerShapeCandidates.some((part) =>
         CHANNEL_SCOPED_SESSION_SHAPES.has(part),
       );
+      const hasLegacyChannelPeerShape =
+        !isChannelScopedSession && typeof sessionScopeParts[1] === "string";
       // Only inherit prior external route metadata for channel-scoped sessions.
       // Channel-agnostic sessions (main, direct:<peer>, etc.) can otherwise
       // leak stale routes across surfaces.
@@ -882,7 +884,7 @@ export const chatHandlers: GatewayRequestHandlers = {
         sessionChannelHint &&
         sessionChannelHint !== INTERNAL_MESSAGE_CHANNEL &&
         !isChannelAgnosticSessionScope &&
-        isChannelScopedSession,
+        (isChannelScopedSession || hasLegacyChannelPeerShape),
       );
       const hasDeliverableRoute =
         canInheritDeliverableRoute &&