diff --git a/CHANGELOG.md b/CHANGELOG.md
index 1911a75bda1..2a6e97310ba 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -58,6 +58,7 @@ Docs: https://docs.openclaw.ai
 - Agents/compaction safeguard pre-check: skip embedded compaction before entering the Pi SDK when a session has no real conversation messages, avoiding unnecessary LLM API calls on idle sessions. (#36451) thanks @Sid-Qin.
 - Config/schema cache key stability: build merged schema cache keys with incremental hashing to avoid large single-string serialization and prevent `RangeError: Invalid string length` on high-cardinality plugin/channel metadata. (#36603) Thanks @powermaster888.
 - iMessage/cron completion announces: strip leaked inline reply tags (for example `[[reply_to:6100]]`) from user-visible completion text so announcement deliveries do not expose threading metadata. (#24600) Thanks @vincentkoc.
+- Control UI/iMessage duplicate reply routing: keep internal webchat turns on dispatcher delivery (instead of origin-channel reroute) so Control UI chats do not duplicate replies into iMessage, while preserving webchat-provider relayed routing for external surfaces. Fixes #33483. Thanks @alicexmolt.
 - Sessions/daily reset transcript archival: archive prior transcript files during stale-session scheduled/daily resets by capturing the previous session entry before rollover, preventing orphaned transcript files on disk. (#35493) Thanks @byungsker.
 - Feishu/group slash command detection: normalize group mention wrappers before command-authorization probing so mention-prefixed commands (for example `@Bot/model` and `@Bot /reset`) are recognized as gateway commands instead of being forwarded to the agent. (#35994) Thanks @liuxiaopai-ai.
 - Agents/context pruning: guard assistant thinking/text char estimation against malformed blocks (missing `thinking`/`text` strings or null entries) so pruning no longer crashes with malformed provider content. (openclaw#35146) thanks @Sid-Qin.
diff --git a/src/auto-reply/reply/dispatch-from-config.test.ts b/src/auto-reply/reply/dispatch-from-config.test.ts
index 78bace08dbc..cb71c9b09ba 100644
--- a/src/auto-reply/reply/dispatch-from-config.test.ts
+++ b/src/auto-reply/reply/dispatch-from-config.test.ts
@@ -399,6 +399,58 @@ describe("dispatchReplyFromConfig", () => {
     expect(dispatcher.sendFinalReply).toHaveBeenCalledTimes(1);
   });
 
+  it("does not route external origin replies when current surface is internal webchat without explicit delivery", async () => {
+    setNoAbort();
+    mocks.routeReply.mockClear();
+    const cfg = emptyConfig;
+    const dispatcher = createDispatcher();
+    const ctx = buildTestCtx({
+      Provider: "webchat",
+      Surface: "webchat",
+      OriginatingChannel: "imessage",
+      OriginatingTo: "imessage:+15550001111",
+    });
+
+    const replyResolver = async (
+      _ctx: MsgContext,
+      _opts?: GetReplyOptions,
+      _cfg?: OpenClawConfig,
+    ) => ({ text: "hi" }) satisfies ReplyPayload;
+    await dispatchReplyFromConfig({ ctx, cfg, dispatcher, replyResolver });
+
+    expect(mocks.routeReply).not.toHaveBeenCalled();
+    expect(dispatcher.sendFinalReply).toHaveBeenCalledTimes(1);
+  });
+
+  it("routes external origin replies for internal webchat turns when explicit delivery is set", async () => {
+    setNoAbort();
+    mocks.routeReply.mockClear();
+    const cfg = emptyConfig;
+    const dispatcher = createDispatcher();
+    const ctx = buildTestCtx({
+      Provider: "webchat",
+      Surface: "webchat",
+      OriginatingChannel: "imessage",
+      OriginatingTo: "imessage:+15550001111",
+      ExplicitDeliverRoute: true,
+    });
+
+    const replyResolver = async (
+      _ctx: MsgContext,
+      _opts?: GetReplyOptions,
+      _cfg?: OpenClawConfig,
+    ) => ({ text: "hi" }) satisfies ReplyPayload;
+    await dispatchReplyFromConfig({ ctx, cfg, dispatcher, replyResolver });
+
+    expect(dispatcher.sendFinalReply).not.toHaveBeenCalled();
+    expect(mocks.routeReply).toHaveBeenCalledWith(
+      expect.objectContaining({
+        channel: "imessage",
+        to: "imessage:+15550001111",
+      }),
+    );
+  });
+
   it("routes media-only tool results when summaries are suppressed", async () => {
     setNoAbort();
     mocks.routeReply.mockClear();
diff --git a/src/auto-reply/reply/dispatch-from-config.ts b/src/auto-reply/reply/dispatch-from-config.ts
index 1a968581cf6..003a8f37435 100644
--- a/src/auto-reply/reply/dispatch-from-config.ts
+++ b/src/auto-reply/reply/dispatch-from-config.ts
@@ -215,8 +215,15 @@ export async function dispatchReplyFromConfig(params: {
   const surfaceChannel = normalizeMessageChannel(ctx.Surface);
   // Prefer provider channel because surface may carry origin metadata in relayed flows.
   const currentSurface = providerChannel ?? surfaceChannel;
+  const isInternalWebchatTurn =
+    currentSurface === INTERNAL_MESSAGE_CHANNEL &&
+    (surfaceChannel === INTERNAL_MESSAGE_CHANNEL || !surfaceChannel) &&
+    ctx.ExplicitDeliverRoute !== true;
   const shouldRouteToOriginating = Boolean(
-    isRoutableChannel(originatingChannel) && originatingTo && originatingChannel !== currentSurface,
+    !isInternalWebchatTurn &&
+    isRoutableChannel(originatingChannel) &&
+    originatingTo &&
+    originatingChannel !== currentSurface,
   );
   const shouldSuppressTyping =
     shouldRouteToOriginating || originatingChannel === INTERNAL_MESSAGE_CHANNEL;
diff --git a/src/auto-reply/templating.ts b/src/auto-reply/templating.ts
index 9c9a7f4d430..ae6a7917ff8 100644
--- a/src/auto-reply/templating.ts
+++ b/src/auto-reply/templating.ts
@@ -159,6 +159,11 @@ export type MsgContext = {
    * The chat/channel/user ID where the reply should be sent.
    */
   OriginatingTo?: string;
+  /**
+   * True when the current turn intentionally requested external delivery to
+   * OriginatingChannel/OriginatingTo, rather than inheriting stale session route metadata.
+   */
+  ExplicitDeliverRoute?: boolean;
   /**
    * Provider-specific parent conversation id for threaded contexts.
    * For Discord threads, this is the parent channel id.
diff --git a/src/gateway/server-methods/chat.directive-tags.test.ts b/src/gateway/server-methods/chat.directive-tags.test.ts
index f9acd15805e..d4f631a21ce 100644
--- a/src/gateway/server-methods/chat.directive-tags.test.ts
+++ b/src/gateway/server-methods/chat.directive-tags.test.ts
@@ -393,6 +393,7 @@ describe("chat directive tag stripping for non-streaming final payloads", () =>
       expect.objectContaining({
         OriginatingChannel: "telegram",
         OriginatingTo: "telegram:6812765697",
+        ExplicitDeliverRoute: true,
         AccountId: "default",
         MessageThreadId: 42,
       }),
@@ -566,6 +567,7 @@ describe("chat directive tag stripping for non-streaming final payloads", () =>
       expect.objectContaining({
         OriginatingChannel: "webchat",
         OriginatingTo: undefined,
+        ExplicitDeliverRoute: false,
         AccountId: undefined,
       }),
     );
diff --git a/src/gateway/server-methods/chat.ts b/src/gateway/server-methods/chat.ts
index 1c750ec0db6..18c00f11118 100644
--- a/src/gateway/server-methods/chat.ts
+++ b/src/gateway/server-methods/chat.ts
@@ -935,6 +935,7 @@ export const chatHandlers: GatewayRequestHandlers = {
         Surface: INTERNAL_MESSAGE_CHANNEL,
         OriginatingChannel: originatingChannel,
         OriginatingTo: originatingTo,
+        ExplicitDeliverRoute: hasDeliverableRoute,
         AccountId: accountId,
         MessageThreadId: messageThreadId,
         ChatType: "direct",