From 087edec93f7be8c3210d06b2430ff08037f43b45 Mon Sep 17 00:00:00 2001
From: Colin <colin@solvely.net>
Date: Mon, 16 Feb 2026 16:07:00 -0500
Subject: [PATCH] feat(slack): add draft preview cleanup lifecycle

---
 src/slack/draft-stream.test.ts                | 50 +++++++++++++++++++
 src/slack/draft-stream.ts                     | 31 +++++++++++-
 src/slack/monitor/message-handler/dispatch.ts |  4 +-
 3 files changed, 83 insertions(+), 2 deletions(-)

diff --git a/src/slack/draft-stream.test.ts b/src/slack/draft-stream.test.ts
index bcb1488ec..4563950e7 100644
--- a/src/slack/draft-stream.test.ts
+++ b/src/slack/draft-stream.test.ts
@@ -103,4 +103,54 @@ describe("createSlackDraftStream", () => {
     expect(edit).not.toHaveBeenCalled();
     expect(warn).toHaveBeenCalledTimes(1);
   });
+
+  it("clear removes preview message when one exists", async () => {
+    const send = vi.fn(async () => ({
+      channelId: "C123",
+      messageId: "111.222",
+    }));
+    const edit = vi.fn(async () => {});
+    const remove = vi.fn(async () => {});
+    const stream = createSlackDraftStream({
+      target: "channel:C123",
+      token: "xoxb-test",
+      throttleMs: 250,
+      send,
+      edit,
+      remove,
+    });
+
+    stream.update("hello");
+    await stream.flush();
+    await stream.clear();
+
+    expect(remove).toHaveBeenCalledTimes(1);
+    expect(remove).toHaveBeenCalledWith("C123", "111.222", {
+      token: "xoxb-test",
+      accountId: undefined,
+    });
+    expect(stream.messageId()).toBeUndefined();
+    expect(stream.channelId()).toBeUndefined();
+  });
+
+  it("clear is a no-op when no preview message exists", async () => {
+    const send = vi.fn(async () => ({
+      channelId: "C123",
+      messageId: "111.222",
+    }));
+    const edit = vi.fn(async () => {});
+    const remove = vi.fn(async () => {});
+    const stream = createSlackDraftStream({
+      target: "channel:C123",
+      token: "xoxb-test",
+      throttleMs: 250,
+      send,
+      edit,
+      remove,
+    });
+
+    await stream.clear();
+
+    expect(remove).not.toHaveBeenCalled();
+  });
 });
diff --git a/src/slack/draft-stream.ts b/src/slack/draft-stream.ts
index 3e918c2e6..3e79a6e00 100644
--- a/src/slack/draft-stream.ts
+++ b/src/slack/draft-stream.ts
@@ -1,4 +1,4 @@
-import { editSlackMessage } from "./actions.js";
+import { deleteSlackMessage, editSlackMessage } from "./actions.js";
 import { sendMessageSlack } from "./send.js";
 
 const SLACK_STREAM_MAX_CHARS = 4000;
@@ -7,6 +7,7 @@ const DEFAULT_THROTTLE_MS = 1000;
 export type SlackDraftStream = {
   update: (text: string) => void;
   flush: () => Promise<void>;
+  clear: () => Promise<void>;
   stop: () => void;
   forceNewMessage: () => void;
   messageId: () => string | undefined;
@@ -25,11 +26,13 @@ export function createSlackDraftStream(params: {
   warn?: (message: string) => void;
   send?: typeof sendMessageSlack;
   edit?: typeof editSlackMessage;
+  remove?: typeof deleteSlackMessage;
 }): SlackDraftStream {
   const maxChars = Math.min(params.maxChars ?? SLACK_STREAM_MAX_CHARS, SLACK_STREAM_MAX_CHARS);
   const throttleMs = Math.max(250, params.throttleMs ?? DEFAULT_THROTTLE_MS);
   const send = params.send ?? sendMessageSlack;
   const edit = params.edit ?? editSlackMessage;
+  const remove = params.remove ?? deleteSlackMessage;
 
   let streamMessageId: string | undefined;
   let streamChannelId: string | undefined;
@@ -152,6 +155,31 @@ export function createSlackDraftStream(params: {
     }
   };
 
+  const clear = async () => {
+    stop();
+    if (inFlightPromise) {
+      await inFlightPromise;
+    }
+    const channelId = streamChannelId;
+    const messageId = streamMessageId;
+    streamChannelId = undefined;
+    streamMessageId = undefined;
+    lastSentText = "";
+    if (!channelId || !messageId) {
+      return;
+    }
+    try {
+      await remove(channelId, messageId, {
+        token: params.token,
+        accountId: params.accountId,
+      });
+    } catch (err) {
+      params.warn?.(
+        `slack stream preview cleanup failed: ${err instanceof Error ? err.message : String(err)}`,
+      );
+    }
+  };
+
   const forceNewMessage = () => {
     streamMessageId = undefined;
     streamChannelId = undefined;
@@ -164,6 +192,7 @@ export function createSlackDraftStream(params: {
   return {
     update,
     flush,
+    clear,
     stop,
     forceNewMessage,
     messageId: () => streamMessageId,
diff --git a/src/slack/monitor/message-handler/dispatch.ts b/src/slack/monitor/message-handler/dispatch.ts
index bebb34ad8..8022c4dbf 100644
--- a/src/slack/monitor/message-handler/dispatch.ts
+++ b/src/slack/monitor/message-handler/dispatch.ts
@@ -135,7 +135,8 @@ export async function dispatchPreparedSlackMessage(prepared: PreparedSlackMessag
           );
         }
       } else if (mediaCount > 0) {
-        draftStream?.stop();
+        await draftStream?.clear();
+        hasStreamedMessage = false;
       }
 
       const replyThreadTs = replyPlan.nextThreadTs();
@@ -215,6 +216,7 @@ export async function dispatchPreparedSlackMessage(prepared: PreparedSlackMessag
   const anyReplyDelivered = queuedFinal || (counts.block ?? 0) > 0 || (counts.final ?? 0) > 0;
 
   if (!anyReplyDelivered) {
+    await draftStream.clear();
     if (prepared.isRoomish) {
       clearHistoryEntriesIfEnabled({
         historyMap: ctx.channelHistories,