diff --git a/src/auto-reply/reply/session-delivery.ts b/src/auto-reply/reply/session-delivery.ts
index 855450bd26d..86370f544ef 100644
--- a/src/auto-reply/reply/session-delivery.ts
+++ b/src/auto-reply/reply/session-delivery.ts
@@ -1,6 +1,6 @@
 import type { SessionEntry } from "../../config/sessions.js";
 import { buildAgentMainSessionKey } from "../../routing/session-key.js";
-import { parseAgentSessionKey } from "../../sessions/session-key-utils.js";
+import { deriveSessionChatType, parseAgentSessionKey } from "../../sessions/session-key-utils.js";
 import {
   deliveryContextFromSession,
   deliveryContextKey,
@@ -38,6 +38,10 @@ function isMainSessionKey(sessionKey?: string): boolean {
   return parsed.rest.trim().toLowerCase() === "main";
 }
 
+function isDirectSessionKey(sessionKey?: string): boolean {
+  return deriveSessionChatType(sessionKey) === "direct";
+}
+
 function isExternalRoutingChannel(channel?: string): channel is string {
   return Boolean(
     channel && channel !== INTERNAL_MESSAGE_CHANNEL && isDeliverableMessageChannel(channel),
@@ -50,7 +54,12 @@ export function resolveLastChannelRaw(params: {
   sessionKey?: string;
 }): string | undefined {
   const originatingChannel = normalizeMessageChannel(params.originatingChannelRaw);
-  if (originatingChannel === INTERNAL_MESSAGE_CHANNEL && isMainSessionKey(params.sessionKey)) {
+  // WebChat should own reply routing for direct-session UI turns, even when the
+  // session previously replied through an external channel like iMessage.
+  if (
+    originatingChannel === INTERNAL_MESSAGE_CHANNEL &&
+    (isMainSessionKey(params.sessionKey) || isDirectSessionKey(params.sessionKey))
+  ) {
     return params.originatingChannelRaw;
   }
   const persistedChannel = normalizeMessageChannel(params.persistedLastChannel);
@@ -77,7 +86,10 @@ export function resolveLastToRaw(params: {
   sessionKey?: string;
 }): string | undefined {
   const originatingChannel = normalizeMessageChannel(params.originatingChannelRaw);
-  if (originatingChannel === INTERNAL_MESSAGE_CHANNEL && isMainSessionKey(params.sessionKey)) {
+  if (
+    originatingChannel === INTERNAL_MESSAGE_CHANNEL &&
+    (isMainSessionKey(params.sessionKey) || isDirectSessionKey(params.sessionKey))
+  ) {
     return params.originatingToRaw || params.toRaw;
   }
   const persistedChannel = normalizeMessageChannel(params.persistedLastChannel);
diff --git a/src/auto-reply/reply/session.test.ts b/src/auto-reply/reply/session.test.ts
index b0feaca4a23..58d6b893267 100644
--- a/src/auto-reply/reply/session.test.ts
+++ b/src/auto-reply/reply/session.test.ts
@@ -1926,6 +1926,43 @@ describe("initSessionState internal channel routing preservation", () => {
     expect(result.sessionEntry.deliveryContext?.to).toBe("group:12345");
   });
 
+  it("lets direct webchat turns override persisted external routes for per-channel-peer sessions", async () => {
+    const storePath = await createStorePath("webchat-direct-route-override-");
+    const sessionKey = "agent:main:imessage:direct:+1555";
+    await writeSessionStoreFast(storePath, {
+      [sessionKey]: {
+        sessionId: "sess-webchat-direct",
+        updatedAt: Date.now(),
+        lastChannel: "imessage",
+        lastTo: "+1555",
+        deliveryContext: {
+          channel: "imessage",
+          to: "+1555",
+        },
+      },
+    });
+    const cfg = {
+      session: { store: storePath, dmScope: "per-channel-peer" },
+    } as OpenClawConfig;
+
+    const result = await initSessionState({
+      ctx: {
+        Body: "reply from control ui",
+        SessionKey: sessionKey,
+        OriginatingChannel: "webchat",
+        OriginatingTo: "session:dashboard",
+        Surface: "webchat",
+      },
+      cfg,
+      commandAuthorized: true,
+    });
+
+    expect(result.sessionEntry.lastChannel).toBe("webchat");
+    expect(result.sessionEntry.lastTo).toBe("session:dashboard");
+    expect(result.sessionEntry.deliveryContext?.channel).toBe("webchat");
+    expect(result.sessionEntry.deliveryContext?.to).toBe("session:dashboard");
+  });
+
   it("keeps persisted external route when OriginatingChannel is non-deliverable", async () => {
     const storePath = await createStorePath("preserve-nondeliverable-route-");
     const sessionKey = "agent:main:discord:channel:24680";