diff --git a/bridge-browser/src/content/result_delivery_controller.ts b/bridge-browser/src/content/result_delivery_controller.ts
index 50fc748..2ecfc05 100644
--- a/bridge-browser/src/content/result_delivery_controller.ts
+++ b/bridge-browser/src/content/result_delivery_controller.ts
@@ -38,7 +38,10 @@ export class ResultDeliveryController {
         }
 
         this.options.toolActivityTracker.updateDelivery(resultBatch.ids, "delivered");
-        UI.triggerAutoSend({ autoSend: this.options.getAutoSend() }, selectors);
+        UI.triggerAutoSend({
+          autoSend: this.options.getAutoSend(),
+          hasFileUpload: delivery.uploaded,
+        }, selectors);
       })
       .catch((error: unknown) => {
         batchFinalized = true;
diff --git a/bridge-browser/src/modules/auto_send.ts b/bridge-browser/src/modules/auto_send.ts
index a8f8cbc..b065e94 100644
--- a/bridge-browser/src/modules/auto_send.ts
+++ b/bridge-browser/src/modules/auto_send.ts
@@ -9,20 +9,18 @@ import {
 } from "./page_selectors";
 import { isElementVisible } from "./dom_helpers";
 import { showUserAttentionNotification } from "./user_attention";
+import { getAutoSendAction, getAutoSendAttemptLimit } from "./auto_send_policy";
 
 let autoSendTimer: NodeJS.Timeout | null = null;
-type AutoSendAction = "ctrl-enter" | "enter" | "button";
 
 const AUTO_SEND_INITIAL_DELAY_MS = 350;
 const AUTO_SEND_SETTLE_MS = 1200;
 const AUTO_SEND_RETRY_MS = 1600;
-const AUTO_SEND_ACTIONS: AutoSendAction[] = [
-  "enter",
-  "ctrl-enter",
-  "button",
-  "enter",
-  "ctrl-enter",
-];
+
+export interface AutoSendConfig {
+  autoSend: boolean;
+  hasFileUpload: boolean;
+}
 
 /**
  * 终止当前正在进行的自动发送轮询机制
@@ -51,7 +49,7 @@ export function cancelAutoSend() {
  * - 4. 如果所有轮次还是失败，系统会弹出通知警告用户。
  */
 export function triggerAutoSend(
-  config: { autoSend: boolean },
+  config: AutoSendConfig,
   domSelectors: SiteSelectors
 ) {
   if (!config.autoSend) {return;}
@@ -61,7 +59,7 @@ export function triggerAutoSend(
   }
 
   let retryCount = 0;
-  const maxRetries = AUTO_SEND_ACTIONS.length;
+  const maxRetries = getAutoSendAttemptLimit(config.hasFileUpload);
 
   const getInputEl = () => getInputAreaElement(domSelectors);
   const getInputValue = (inputEl: HTMLElement): string => {
@@ -107,7 +105,7 @@ export function triggerAutoSend(
       inputEl.dispatchEvent(new Event("change", { bubbles: true }));
     }
 
-    const action = AUTO_SEND_ACTIONS[retryCount] ?? "enter";
+    const action = getAutoSendAction(retryCount);
     if (action === "ctrl-enter" || action === "enter") {
       if (inputEl) {
         const withCtrl = action === "ctrl-enter";
diff --git a/bridge-browser/src/modules/auto_send_policy.ts b/bridge-browser/src/modules/auto_send_policy.ts
new file mode 100644
index 0000000..b8b2af1
--- /dev/null
+++ b/bridge-browser/src/modules/auto_send_policy.ts
@@ -0,0 +1,18 @@
+export type AutoSendAction = "ctrl-enter" | "enter" | "button";
+
+const AUTO_SEND_ACTIONS: readonly AutoSendAction[] = [
+  "enter",
+  "ctrl-enter",
+  "button",
+  "enter",
+  "ctrl-enter",
+];
+const AUTO_SEND_FILE_ATTEMPTS = 20;
+
+export function getAutoSendAttemptLimit(hasFileUpload: boolean): number {
+  return hasFileUpload ? AUTO_SEND_FILE_ATTEMPTS : AUTO_SEND_ACTIONS.length;
+}
+
+export function getAutoSendAction(attemptIndex: number): AutoSendAction {
+  return AUTO_SEND_ACTIONS[attemptIndex % AUTO_SEND_ACTIONS.length] ?? "enter";
+}
diff --git a/bridge-browser/test/auto_send_policy.test.ts b/bridge-browser/test/auto_send_policy.test.ts
new file mode 100644
index 0000000..feebd1e
--- /dev/null
+++ b/bridge-browser/test/auto_send_policy.test.ts
@@ -0,0 +1,35 @@
+import {
+  getAutoSendAction,
+  getAutoSendAttemptLimit,
+} from "../src/modules/auto_send_policy";
+
+function main(): void {
+  runTest("keeps five attempts for text-only sends", () => {
+    assertEqual(getAutoSendAttemptLimit(false), 5, "text-only attempt limit changed");
+  });
+  runTest("allows twenty attempts after a file paste", () => {
+    assertEqual(getAutoSendAttemptLimit(true), 20, "file upload attempt limit was not extended");
+  });
+  runTest("repeats the fallback action sequence during extended retries", () => {
+    assertEqual(getAutoSendAction(2), "button", "initial button fallback changed");
+    assertEqual(getAutoSendAction(7), "button", "extended retries did not repeat the button fallback");
+  });
+}
+
+function runTest(name: string, test: () => void): void {
+  try {
+    test();
+    console.log(`PASS ${name}`);
+  } catch (error) {
+    console.error(`FAIL ${name}`);
+    throw error;
+  }
+}
+
+function assertEqual(actual: unknown, expected: unknown, message: string): void {
+  if (actual !== expected) {
+    throw new Error(`${message}: expected ${String(expected)}, received ${String(actual)}`);
+  }
+}
+
+main();
diff --git a/bridge-browser/test/result_delivery.test.ts b/bridge-browser/test/result_delivery.test.ts
index 29a9eac..6091943 100644
--- a/bridge-browser/test/result_delivery.test.ts
+++ b/bridge-browser/test/result_delivery.test.ts
@@ -16,6 +16,7 @@ async function main(): Promise<void> {
     assertEqual(page.actions[2], "write", "result text was written before the attachment wait");
     assert(page.input.innerText.includes('"status": "success"'), "acknowledged attachment became an error");
     assert(delivery.delivered, "acknowledged result was not delivered");
+    assert(delivery.uploaded, "dispatched attachment was not reported to auto-send");
   });
   await runTest("reports an unacknowledged paste for only its attachment result", async () => {
     const page = installFakePage(false);
@@ -30,6 +31,7 @@ async function main(): Promise<void> {
     assert(page.input.innerText.includes('"name": "read_file"'), "unrelated result was lost");
     assert(page.input.innerText.includes('"output": "text result"'), "unrelated result was changed");
     assert(delivery.delivered, "attachment failure text did not remain sendable");
+    assert(delivery.uploaded, "unacknowledged attachment dispatch was not reported to auto-send");
   });
   await runTest("acknowledges each attachment group independently", async () => {
     const page = installFakePage([true, false]);