diff --git a/src/auto-reply/reply/session.test.ts b/src/auto-reply/reply/session.test.ts
index 3a25c5d1552..9a85f277223 100644
--- a/src/auto-reply/reply/session.test.ts
+++ b/src/auto-reply/reply/session.test.ts
@@ -1474,13 +1474,50 @@ describe("initSessionState internal channel routing preservation", () => {
         Body: "internal follow-up",
         SessionKey: sessionKey,
         OriginatingChannel: "webchat",
+        OriginatingTo: "session:dashboard",
       },
       cfg,
       commandAuthorized: true,
     });
 
     expect(result.sessionEntry.lastChannel).toBe("telegram");
+    expect(result.sessionEntry.lastTo).toBe("group:12345");
     expect(result.sessionEntry.deliveryContext?.channel).toBe("telegram");
+    expect(result.sessionEntry.deliveryContext?.to).toBe("group:12345");
+  });
+
+  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";
+    await saveSessionStore(storePath, {
+      [sessionKey]: {
+        sessionId: "sess-2",
+        updatedAt: Date.now(),
+        lastChannel: "discord",
+        lastTo: "channel:24680",
+        deliveryContext: {
+          channel: "discord",
+          to: "channel:24680",
+        },
+      },
+    });
+    const cfg = { session: { store: storePath } } as OpenClawConfig;
+
+    const result = await initSessionState({
+      ctx: {
+        Body: "internal handoff",
+        SessionKey: sessionKey,
+        OriginatingChannel: "sessions_send",
+        OriginatingTo: "session:handoff",
+      },
+      cfg,
+      commandAuthorized: true,
+    });
+
+    expect(result.sessionEntry.lastChannel).toBe("discord");
+    expect(result.sessionEntry.lastTo).toBe("channel:24680");
+    expect(result.sessionEntry.deliveryContext?.channel).toBe("discord");
+    expect(result.sessionEntry.deliveryContext?.to).toBe("channel:24680");
   });
 
   it("uses session key channel hint when first turn is internal webchat", async () => {
diff --git a/src/auto-reply/reply/session.ts b/src/auto-reply/reply/session.ts
index ed789ece8da..88711b140b4 100644
--- a/src/auto-reply/reply/session.ts
+++ b/src/auto-reply/reply/session.ts
@@ -62,6 +62,12 @@ function resolveSessionKeyChannelHint(sessionKey?: string): string | undefined {
   return normalizeMessageChannel(head);
 }
 
+function isExternalRoutingChannel(channel?: string): channel is string {
+  return Boolean(
+    channel && channel !== INTERNAL_MESSAGE_CHANNEL && isDeliverableMessageChannel(channel),
+  );
+}
+
 function resolveLastChannelRaw(params: {
   originatingChannelRaw?: string;
   persistedLastChannel?: string;
@@ -71,26 +77,44 @@ function resolveLastChannelRaw(params: {
   const persistedChannel = normalizeMessageChannel(params.persistedLastChannel);
   const sessionKeyChannelHint = resolveSessionKeyChannelHint(params.sessionKey);
   let resolved = params.originatingChannelRaw || params.persistedLastChannel;
-  // Internal webchat/system turns should not overwrite previously known external
-  // delivery routes (or explicit channel hints encoded in the session key).
-  if (originatingChannel === INTERNAL_MESSAGE_CHANNEL) {
-    if (
-      persistedChannel &&
-      persistedChannel !== INTERNAL_MESSAGE_CHANNEL &&
-      isDeliverableMessageChannel(persistedChannel)
-    ) {
+  // Internal/non-deliverable sources should not overwrite previously known
+  // external delivery routes (or explicit channel hints from the session key).
+  if (!isExternalRoutingChannel(originatingChannel)) {
+    if (isExternalRoutingChannel(persistedChannel)) {
       resolved = persistedChannel;
-    } else if (
-      sessionKeyChannelHint &&
-      sessionKeyChannelHint !== INTERNAL_MESSAGE_CHANNEL &&
-      isDeliverableMessageChannel(sessionKeyChannelHint)
-    ) {
+    } else if (isExternalRoutingChannel(sessionKeyChannelHint)) {
       resolved = sessionKeyChannelHint;
     }
   }
   return resolved;
 }
 
+function resolveLastToRaw(params: {
+  originatingChannelRaw?: string;
+  originatingToRaw?: string;
+  toRaw?: string;
+  persistedLastTo?: string;
+  persistedLastChannel?: string;
+  sessionKey?: string;
+}): string | undefined {
+  const originatingChannel = normalizeMessageChannel(params.originatingChannelRaw);
+  const persistedChannel = normalizeMessageChannel(params.persistedLastChannel);
+  const sessionKeyChannelHint = resolveSessionKeyChannelHint(params.sessionKey);
+
+  // When the turn originates from an internal/non-deliverable source, do not
+  // replace an established external destination with internal routing ids
+  // (e.g., session/webchat ids).
+  if (!isExternalRoutingChannel(originatingChannel)) {
+    const hasExternalFallback =
+      isExternalRoutingChannel(persistedChannel) || isExternalRoutingChannel(sessionKeyChannelHint);
+    if (hasExternalFallback && params.persistedLastTo) {
+      return params.persistedLastTo;
+    }
+  }
+
+  return params.originatingToRaw || params.toRaw || params.persistedLastTo;
+}
+
 export type SessionInitResult = {
   sessionCtx: TemplateContext;
   sessionEntry: SessionEntry;
@@ -422,7 +446,14 @@ export async function initSessionState(params: {
     persistedLastChannel: baseEntry?.lastChannel,
     sessionKey,
   });
-  const lastToRaw = ctx.OriginatingTo || ctx.To || baseEntry?.lastTo;
+  const lastToRaw = resolveLastToRaw({
+    originatingChannelRaw,
+    originatingToRaw: ctx.OriginatingTo,
+    toRaw: ctx.To,
+    persistedLastTo: baseEntry?.lastTo,
+    persistedLastChannel: baseEntry?.lastChannel,
+    sessionKey,
+  });
   const lastAccountIdRaw = ctx.AccountId || baseEntry?.lastAccountId;
   // Only fall back to persisted threadId for thread sessions.  Non-thread
   // sessions (e.g. DM without topics) must not inherit a stale threadId from a