fix(followup): scope session dedupe fingerprints to single-target runs

src/auto-reply/reply/followup-runner.test.ts

@@ -506,6 +506,40 @@ describe("createFollowupRunner messaging tool dedupe", () => {
     expect(onBlockReply).toHaveBeenCalled();
   });
 
+  it("does not reuse session-level text dedupe when prior run had multiple messaging targets", async () => {
+    const onBlockReply = vi.fn(async () => {});
+    const sessionEntry: SessionEntry = {
+      sessionId: "session",
+      updatedAt: Date.now(),
+      lastMessagingToolSessionId: "session",
+      lastMessagingToolSentAt: Date.now(),
+      lastMessagingToolSentTexts: ["hello world!"],
+      lastMessagingToolSentTargets: [
+        { tool: "message", provider: "telegram", to: "123" },
+        { tool: "message", provider: "telegram", to: "999" },
+      ],
+    };
+    const sessionStore: Record<string, SessionEntry> = { main: sessionEntry };
+
+    runEmbeddedPiAgentMock.mockResolvedValueOnce({
+      payloads: [{ text: "hello world!" }],
+      meta: {},
+    });
+
+    const runner = createMessagingDedupeRunner(onBlockReply, {
+      sessionEntry,
+      sessionStore,
+      sessionKey: "main",
+    });
+
+    await runner({
+      ...baseQueuedRun("telegram"),
+      originatingTo: "123",
+    });
+
+    expect(onBlockReply).toHaveBeenCalled();
+  });
+
   it("drops media URL from payload when messaging tool already sent it", async () => {
     const onBlockReply = vi.fn(async () => {});
     runEmbeddedPiAgentMock.mockResolvedValueOnce({

src/auto-reply/reply/followup-runner.ts

@@ -335,22 +335,27 @@ export function createFollowupRunner(params: {
         typeof sessionEntry?.lastMessagingToolSentAt === "number" &&
         sessionEntry?.lastMessagingToolSessionId === queued.run.sessionId &&
         now - sessionEntry.lastMessagingToolSentAt <= RECENT_MESSAGING_TOOL_DEDUPE_WINDOW_MS;
+      const previousSentTargets = sessionEntry?.lastMessagingToolSentTargets ?? [];
       const recentTargetMatch =
         recentWindowActive &&
         shouldSuppressMessagingToolReplies({
           messageProvider,
-          messagingToolSentTargets: sessionEntry?.lastMessagingToolSentTargets,
+          messagingToolSentTargets: previousSentTargets,
           originatingTo,
           accountId: originAccountId,
         });
+      const canReuseSessionDedupeFingerprints =
+        recentTargetMatch && previousSentTargets.length <= 1;
 
       const sentTexts = [
         ...(runResult.messagingToolSentTexts ?? []),
-        ...(recentTargetMatch ? (sessionEntry?.lastMessagingToolSentTexts ?? []) : []),
+        ...(canReuseSessionDedupeFingerprints ? (sessionEntry?.lastMessagingToolSentTexts ?? []) : []),
       ];
       const sentMediaUrls = [
         ...(runResult.messagingToolSentMediaUrls ?? []),
-        ...(recentTargetMatch ? (sessionEntry?.lastMessagingToolSentMediaUrls ?? []) : []),
+        ...(canReuseSessionDedupeFingerprints
+          ? (sessionEntry?.lastMessagingToolSentMediaUrls ?? [])
+          : []),
       ];
       // Keep target-based suppression scoped to the current run only.
       // Session-level dedupe state is used for text/media duplicate filtering when target matches.