diff --git a/src/gateway/server-methods/chat.directive-tags.test.ts b/src/gateway/server-methods/chat.directive-tags.test.ts
index 0ea0e0181c2..1f72c5d15b5 100644
--- a/src/gateway/server-methods/chat.directive-tags.test.ts
+++ b/src/gateway/server-methods/chat.directive-tags.test.ts
@@ -4,7 +4,7 @@ import path from "node:path";
 import { CURRENT_SESSION_VERSION } from "@mariozechner/pi-coding-agent";
 import { afterEach, describe, expect, it, vi } from "vitest";
 import type { MsgContext } from "../../auto-reply/templating.js";
-import { GATEWAY_CLIENT_CAPS } from "../protocol/client-info.js";
+import { GATEWAY_CLIENT_CAPS, GATEWAY_CLIENT_MODES } from "../protocol/client-info.js";
 import type { GatewayRequestContext } from "./types.js";
 
 const mockState = vi.hoisted(() => ({
@@ -550,6 +550,47 @@ describe("chat directive tag stripping for non-streaming final payloads", () =>
     );
   });
 
+  it("chat.send does not inherit external delivery context for UI clients on main sessions", async () => {
+    createTranscriptFixture("openclaw-chat-send-main-ui-routes-");
+    mockState.finalText = "ok";
+    mockState.sessionEntry = {
+      deliveryContext: {
+        channel: "whatsapp",
+        to: "whatsapp:+8613800138000",
+        accountId: "default",
+      },
+      lastChannel: "whatsapp",
+      lastTo: "whatsapp:+8613800138000",
+      lastAccountId: "default",
+    };
+    const respond = vi.fn();
+    const context = createChatContext();
+
+    await runNonStreamingChatSend({
+      context,
+      respond,
+      idempotencyKey: "idem-main-ui-routes",
+      client: {
+        connect: {
+          client: {
+            mode: GATEWAY_CLIENT_MODES.UI,
+            id: "openclaw-tui",
+          },
+        },
+      } as unknown,
+      sessionKey: "agent:main:main",
+      expectBroadcast: false,
+    });
+
+    expect(mockState.lastDispatchCtx).toEqual(
+      expect.objectContaining({
+        OriginatingChannel: "webchat",
+        OriginatingTo: undefined,
+        AccountId: undefined,
+      }),
+    );
+  });
+
   it("chat.send does not inherit external delivery context for non-channel custom sessions", async () => {
     createTranscriptFixture("openclaw-chat-send-custom-no-cross-route-");
     mockState.finalText = "ok";
diff --git a/src/gateway/server-methods/chat.ts b/src/gateway/server-methods/chat.ts
index 13feee2d131..e90fcf15611 100644
--- a/src/gateway/server-methods/chat.ts
+++ b/src/gateway/server-methods/chat.ts
@@ -17,7 +17,11 @@ import {
   stripInlineDirectiveTagsForDisplay,
   stripInlineDirectiveTagsFromMessageForDisplay,
 } from "../../utils/directive-tags.js";
-import { INTERNAL_MESSAGE_CHANNEL, normalizeMessageChannel } from "../../utils/message-channel.js";
+import {
+  INTERNAL_MESSAGE_CHANNEL,
+  isWebchatClient,
+  normalizeMessageChannel,
+} from "../../utils/message-channel.js";
 import {
   abortChatRunById,
   abortChatRunsForSessionKey,
@@ -28,7 +32,11 @@ import {
 } from "../chat-abort.js";
 import { type ChatImageContent, parseMessageWithAttachments } from "../chat-attachments.js";
 import { stripEnvelopeFromMessage, stripEnvelopeFromMessages } from "../chat-sanitize.js";
-import { GATEWAY_CLIENT_CAPS, hasGatewayClientCap } from "../protocol/client-info.js";
+import {
+  GATEWAY_CLIENT_CAPS,
+  GATEWAY_CLIENT_MODES,
+  hasGatewayClientCap,
+} from "../protocol/client-info.js";
 import {
   ErrorCodes,
   errorShape,
@@ -880,14 +888,18 @@ export const chatHandlers: GatewayRequestHandlers = {
         !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.
+      const clientMode = client?.connect?.client?.mode;
+      const isFromWebchatClient =
+        isWebchatClient(client?.connect?.client) || clientMode === GATEWAY_CLIENT_MODES.UI;
+      // Channel-agnostic session scopes (main, direct:<peer>, etc.) can leak
+      // stale routes across surfaces. Allow main sessions only from non-Webchat
+      // clients so CLI replies can keep the last WA/Telegram route.
       const canInheritDeliverableRoute = Boolean(
         sessionChannelHint &&
         sessionChannelHint !== INTERNAL_MESSAGE_CHANNEL &&
-        !isChannelAgnosticSessionScope &&
-        (isChannelScopedSession || hasLegacyChannelPeerShape),
+        ((!isChannelAgnosticSessionScope &&
+          (isChannelScopedSession || hasLegacyChannelPeerShape)) ||
+          (sessionChannelHint === "main" && client?.connect !== undefined && !isFromWebchatClient)),
       );
       const hasDeliverableRoute =
         canInheritDeliverableRoute &&