diff --git a/extensions/discord/src/monitor/message-handler.draft-preview.ts b/extensions/discord/src/monitor/message-handler.draft-preview.ts
index 3e6f19ecfec..c1ab9b2672e 100644
--- a/extensions/discord/src/monitor/message-handler.draft-preview.ts
+++ b/extensions/discord/src/monitor/message-handler.draft-preview.ts
@@ -256,12 +256,14 @@ export function createDiscordDraftPreviewController(params: {
         );
       }
       const alreadyStarted = progressDraftGate.hasStarted;
+      let progressActive = false;
       if (shouldStartDiscordProgressDraftNow(line)) {
         await progressDraftGate.startNow();
+        progressActive = progressDraftGate.hasStarted;
       } else {
-        await progressDraftGate.noteWork();
+        progressActive = await progressDraftGate.noteWork();
       }
-      if (alreadyStarted && progressDraftGate.hasStarted) {
+      if ((alreadyStarted || progressActive) && progressDraftGate.hasStarted) {
         await renderProgressDraft();
       }
     },
@@ -294,9 +296,8 @@ export function createDiscordDraftPreviewController(params: {
         }
         lastReasoningProgressLine = normalized;
       }
-      const alreadyStarted = progressDraftGate.hasStarted;
-      await progressDraftGate.noteWork();
-      if (alreadyStarted && progressDraftGate.hasStarted) {
+      const progressActive = await progressDraftGate.noteWork();
+      if (progressActive && progressDraftGate.hasStarted) {
         await renderProgressDraft();
       }
     },
diff --git a/extensions/matrix/src/matrix/monitor/handler.ts b/extensions/matrix/src/matrix/monitor/handler.ts
index ebeddc69c76..26992f01e35 100644
--- a/extensions/matrix/src/matrix/monitor/handler.ts
+++ b/extensions/matrix/src/matrix/monitor/handler.ts
@@ -1650,8 +1650,8 @@ export function createMatrixRoomMessageHandler(params: MatrixMonitorHandlerParam
           );
         }
         const alreadyStarted = progressDraftGate.hasStarted;
-        await progressDraftGate.noteWork();
-        if (alreadyStarted && progressDraftGate.hasStarted) {
+        const progressActive = await progressDraftGate.noteWork();
+        if ((alreadyStarted || progressActive) && progressDraftGate.hasStarted) {
           renderProgressDraft();
         }
       };
diff --git a/extensions/msteams/src/reply-stream-controller.ts b/extensions/msteams/src/reply-stream-controller.ts
index 36c879e9459..27c886ddb91 100644
--- a/extensions/msteams/src/reply-stream-controller.ts
+++ b/extensions/msteams/src/reply-stream-controller.ts
@@ -215,10 +215,10 @@ export function createTeamsReplyStreamController(params: {
         return;
       }
       const hadStarted = progressDraftGate.hasStarted;
-      await progressDraftGate.noteWork();
+      const progressActive = await progressDraftGate.noteWork();
       // If the gate was already started, the call above is a no-op — refresh
       // the informative line manually so the latest progress lines render.
-      if (hadStarted && progressDraftGate.hasStarted) {
+      if ((hadStarted || progressActive) && progressDraftGate.hasStarted) {
         renderInformativeUpdate();
       }
     },
@@ -252,8 +252,8 @@ export function createTeamsReplyStreamController(params: {
         }
       }
       const hadStarted = progressDraftGate.hasStarted;
-      await progressDraftGate.noteWork();
-      if (hadStarted && progressDraftGate.hasStarted) {
+      const progressActive = await progressDraftGate.noteWork();
+      if ((hadStarted || progressActive) && progressDraftGate.hasStarted) {
         renderInformativeUpdate();
       }
     },
diff --git a/extensions/slack/src/monitor/message-handler/dispatch.ts b/extensions/slack/src/monitor/message-handler/dispatch.ts
index f01b95fb6dc..3a492973648 100644
--- a/extensions/slack/src/monitor/message-handler/dispatch.ts
+++ b/extensions/slack/src/monitor/message-handler/dispatch.ts
@@ -1492,8 +1492,8 @@ export async function dispatchPreparedSlackMessage(prepared: PreparedSlackMessag
         return;
       }
       const alreadyStarted = progressDraftGate.hasStarted;
-      await progressDraftGate.noteWork();
-      if (alreadyStarted && progressDraftGate.hasStarted) {
+      const progressActive = await progressDraftGate.noteWork();
+      if ((alreadyStarted || progressActive) && progressDraftGate.hasStarted) {
         await refreshStartedProgressDraft();
       }
       return;
@@ -1533,12 +1533,15 @@ export async function dispatchPreparedSlackMessage(prepared: PreparedSlackMessag
         await updateNativeProgressStream();
       } else {
         await progressDraftGate.startNow();
+        if (progressDraftGate.hasStarted) {
+          await updateNativeProgressStream();
+        }
       }
       return;
     }
     const alreadyStarted = progressDraftGate.hasStarted;
-    await progressDraftGate.noteWork();
-    if (alreadyStarted && progressDraftGate.hasStarted) {
+    const progressActive = await progressDraftGate.noteWork();
+    if ((alreadyStarted || progressActive) && progressDraftGate.hasStarted) {
       await refreshStartedProgressDraft();
     }
   };
diff --git a/extensions/telegram/src/bot-message-dispatch.ts b/extensions/telegram/src/bot-message-dispatch.ts
index 568fa449820..7aef61810a2 100644
--- a/extensions/telegram/src/bot-message-dispatch.ts
+++ b/extensions/telegram/src/bot-message-dispatch.ts
@@ -1046,17 +1046,16 @@ export const dispatchTelegramMessage = async ({
     }
     streamToolProgressLines = nextLines;
     if (options?.startImmediately) {
-      const alreadyStarted = progressDraftGate.hasStarted;
       await progressDraftGate.startNow();
-      if (alreadyStarted && progressDraftGate.hasStarted) {
+      if (progressDraftGate.hasStarted) {
         await renderProgressDraft();
         return true;
       }
       return progressDraftGate.hasStarted;
     }
     const alreadyStarted = progressDraftGate.hasStarted;
-    await progressDraftGate.noteWork();
-    if (alreadyStarted && progressDraftGate.hasStarted) {
+    const progressActive = await progressDraftGate.noteWork();
+    if ((alreadyStarted || progressActive) && progressDraftGate.hasStarted) {
       await renderProgressDraft();
       return true;
     }
diff --git a/src/channels/streaming.ts b/src/channels/streaming.ts
index 72baeddbbff..ce266928891 100644
--- a/src/channels/streaming.ts
+++ b/src/channels/streaming.ts
@@ -539,9 +539,29 @@ export function createChannelProgressDraftGate(params: {
     if (disposed || started) {
       return startPromise ?? Promise.resolve();
     }
-    started = true;
+    if (startPromise) {
+      return startPromise;
+    }
     clearTimer();
-    startPromise = Promise.resolve().then(params.onStart);
+    started = true;
+    const nextStart = Promise.resolve()
+      .then(params.onStart)
+      .then(() => {
+        if (disposed) {
+          started = false;
+        }
+        if (startPromise === nextStart) {
+          startPromise = undefined;
+        }
+      })
+      .catch((error: unknown) => {
+        if (startPromise === nextStart) {
+          startPromise = undefined;
+        }
+        started = false;
+        throw error;
+      });
+    startPromise = nextStart;
     return startPromise;
   };
 
@@ -567,12 +587,16 @@ export function createChannelProgressDraftGate(params: {
         return false;
       }
       workEvents += 1;
+      if (startPromise) {
+        await startPromise;
+        return started;
+      }
       if (started) {
         return true;
       }
       if (workEvents > 1) {
         await start();
-        return true;
+        return started;
       }
       schedule();
       return false;
@@ -582,6 +606,7 @@ export function createChannelProgressDraftGate(params: {
     },
     cancel(): void {
       disposed = true;
+      started = false;
       clearTimer();
     },
   };
diff --git a/src/plugin-sdk/channel-streaming.test.ts b/src/plugin-sdk/channel-streaming.test.ts
index 1539876accd..58bed9b6341 100644
--- a/src/plugin-sdk/channel-streaming.test.ts
+++ b/src/plugin-sdk/channel-streaming.test.ts
@@ -590,6 +590,103 @@ describe("channel-streaming", () => {
     expect(onStart).toHaveBeenCalledTimes(1);
   });
 
+  it("does not report started when delayed progress startup rejects", async () => {
+    vi.useFakeTimers();
+    const onStart = vi
+      .fn<() => Promise<void>>()
+      .mockRejectedValueOnce(new Error("draft unavailable"))
+      .mockResolvedValueOnce(undefined);
+    const gate = createChannelProgressDraftGate({ onStart });
+
+    await expect(gate.noteWork()).resolves.toBe(false);
+    await vi.advanceTimersByTimeAsync(5_000);
+
+    expect(onStart).toHaveBeenCalledTimes(1);
+    expect(gate.hasStarted).toBe(false);
+
+    await expect(gate.noteWork()).resolves.toBe(true);
+
+    expect(onStart).toHaveBeenCalledTimes(2);
+    expect(gate.hasStarted).toBe(true);
+  });
+
+  it("keeps concurrent progress startup single-flight until onStart resolves", async () => {
+    vi.useFakeTimers();
+    let resolveStart: (() => void) | undefined;
+    const onStart = vi.fn(
+      () =>
+        new Promise<void>((resolve) => {
+          resolveStart = resolve;
+        }),
+    );
+    const gate = createChannelProgressDraftGate({ onStart });
+
+    await gate.noteWork();
+    const firstStart = gate.noteWork();
+    const secondStart = gate.startNow();
+    await Promise.resolve();
+
+    expect(onStart).toHaveBeenCalledTimes(1);
+    expect(gate.hasStarted).toBe(true);
+
+    resolveStart?.();
+    await expect(firstStart).resolves.toBe(true);
+    await expect(secondStart).resolves.toBeUndefined();
+
+    expect(onStart).toHaveBeenCalledTimes(1);
+    expect(gate.hasStarted).toBe(true);
+  });
+
+  it("does not report active when cancel wins the startup race", async () => {
+    vi.useFakeTimers();
+    let resolveStart: (() => void) | undefined;
+    const onStart = vi.fn(
+      () =>
+        new Promise<void>((resolve) => {
+          resolveStart = resolve;
+        }),
+    );
+    const gate = createChannelProgressDraftGate({ onStart });
+
+    await gate.noteWork();
+    const startResult = gate.noteWork();
+    await Promise.resolve();
+
+    expect(onStart).toHaveBeenCalledTimes(1);
+    gate.cancel();
+
+    resolveStart?.();
+
+    await expect(startResult).resolves.toBe(false);
+    expect(gate.hasStarted).toBe(false);
+  });
+
+  it("joins explicit startup before applying the first-work delay", async () => {
+    vi.useFakeTimers();
+    let resolveStart: (() => void) | undefined;
+    const onStart = vi.fn(
+      () =>
+        new Promise<void>((resolve) => {
+          resolveStart = resolve;
+        }),
+    );
+    const gate = createChannelProgressDraftGate({ onStart });
+
+    const explicitStart = gate.startNow();
+    await Promise.resolve();
+    const workDuringStart = gate.noteWork();
+
+    expect(onStart).toHaveBeenCalledTimes(1);
+    expect(gate.hasStarted).toBe(true);
+
+    resolveStart?.();
+
+    await expect(explicitStart).resolves.toBeUndefined();
+    await expect(workDuringStart).resolves.toBe(true);
+    expect(onStart).toHaveBeenCalledTimes(1);
+    expect(gate.hasStarted).toBe(true);
+  });
+
   it("ignores message-like tools for progress draft work", () => {
     expect(isChannelProgressDraftWorkToolName("message")).toBe(false);
     expect(isChannelProgressDraftWorkToolName("react")).toBe(false);