diff --git a/CHANGELOG.md b/CHANGELOG.md
index 3f5d02677..f841ffb2b 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,6 +4,7 @@
 
 ### Fixed
 
+- Browser: recover when ChatGPT leaves an attachment-bearing image prompt staged after a no-op send-button click by submitting it once via Enter; normalize ProseMirror paragraph whitespace and persist `promptSubmitted` only after the user turn is observable.
 - Browser: attach to running Chrome when `DevToolsActivePort` metadata is absent, with IPv6 support and bounded endpoint retries that include response-body reads. Fixes #414. Thanks @devYRPauli!
 - Browser: recognize collision-renamed attachment chips, including short filenames, while keeping Unicode filename boundaries and visible extensions distinct across upload and send checks. Fixes #393. Thanks @devYRPauli!
 - Browser: select and verify thinking effort in ChatGPT's direct-slider picker without an Advanced submenu, keeping explicit Pro requests fail-closed. Fixes #422.
diff --git a/docs/manual-tests.md b/docs/manual-tests.md
index a4aaf28b8..47e224b9f 100644
--- a/docs/manual-tests.md
+++ b/docs/manual-tests.md
@@ -134,6 +134,12 @@ Debug note: when you have a live ChatGPT tab open under a DevTools port and need
 - Remember: the browser composer now pastes only the user prompt (plus any inline file blocks). If you see the default “You are Oracle…” text or other system-prefixed content in the ChatGPT composer, something regressed in `assembleBrowserPrompt` and you should stop and file a bug.
 - Heartbeats: Browser runs emit `--heartbeat` status while waiting. Long Thinking/Pro runs should show `[browser] ChatGPT thinking ...` or `[browser] Waiting for ChatGPT response ...`; the log must not include reasoning text from the side panel.
 
+4b. **ChatGPT image generation with a reference image**
+
+- Run `oracle --engine browser --browser-manual-login --model gpt-5.6-sol --browser-thinking-time light --browser-attachments always --file /tmp/reference.png --generate-image /tmp/oracle-image-smoke.png --prompt "Generate a simple square image based on the reference."`.
+- Confirm the session runtime records `promptSubmitted: true`, ChatGPT shows the submitted user turn (not a prompt left in the composer), and `/tmp/oracle-image-smoke.png` is a valid downloaded image.
+- If the send-button click is a no-op, expect `Send click left the prompt staged; submitting once via Enter` before the user turn appears.
+
 ## Post-Run Validation
 
 - `oracle session <id>` should replay the transcript with markdown.
diff --git a/docs/windows-work.md b/docs/windows-work.md
index 5f9125d9a..6f36e46ce 100644
--- a/docs/windows-work.md
+++ b/docs/windows-work.md
@@ -12,3 +12,4 @@ Read this file whenever you're working from Windows and add new findings so the
 Future Windows gotchas belong here. Update this doc when you learn something new.
 
 - ChatGPT sidebar/history labels can include phrases like "Login setup instruction"; login probes must match exact auth CTAs, not any visible text starting with login, or manual-login automation loops forever before typing.
+- On the Windows ChatGPT home composer, a reference-image upload can leave the prompt staged even after a trusted click on the visible enabled `data-testid="send-button"`. An Enter fallback must compare canonical whitespace because ProseMirror inserts extra paragraph newlines; gate the fallback on no new turn/no stop control, and record `promptSubmitted` only after the user turn is observable.
diff --git a/src/browser/actions/promptComposer.ts b/src/browser/actions/promptComposer.ts
index 7f04f745e..fa28291ad 100644
--- a/src/browser/actions/promptComposer.ts
+++ b/src/browser/actions/promptComposer.ts
@@ -5,6 +5,7 @@ import {
   PROMPT_FALLBACK_SELECTOR,
   SEND_BUTTON_SELECTORS,
   STOP_BUTTON_SELECTOR,
+  STOP_BUTTON_SELECTORS,
   ASSISTANT_ROLE_SELECTOR,
 } from "../constants.js";
 import {
@@ -235,18 +236,107 @@ export async function submitPrompt(
     logger("Submitted prompt via Enter key");
   } else {
     logger("Clicked send button");
+    await submitStagedPromptViaEnter(
+      runtime,
+      input,
+      prompt,
+      deps.baselineTurns ?? undefined,
+      logger,
+    );
   }
-  await deps.onPromptSubmitted?.();
 
   const commitTimeoutMs = Math.max(60_000, deps.inputTimeoutMs ?? 0);
   // Learned: the send button can succeed but the turn doesn't appear immediately; verify commit via turns/stop button.
-  return await verifyPromptCommitted(
+  const committedTurns = await verifyPromptCommitted(
     runtime,
     prompt,
     commitTimeoutMs,
     logger,
     deps.baselineTurns ?? undefined,
   );
+  // A click is only an attempt: persist promptSubmitted after ChatGPT exposes
+  // the user turn so no-op controls cannot make an unsubmitted session look live.
+  await deps.onPromptSubmitted?.();
+  return committedTurns;
+}
+
+async function submitStagedPromptViaEnter(
+  Runtime: ChromeClient["Runtime"],
+  Input: ChromeClient["Input"],
+  prompt: string,
+  baselineTurns: number | undefined,
+  logger: BrowserLogger,
+): Promise<boolean> {
+  // ChatGPT can leave the composer untouched after a trusted click, especially
+  // when an image attachment is present. Give the click a chance to commit, then
+  // use Enter only while the same prompt is still staged and no generation/turn
+  // signal has appeared. ProseMirror inserts extra paragraph newlines, so compare
+  // canonical whitespace rather than raw innerText.
+  await delay(750);
+  const normalizedPrompt = prompt.replace(/\s+/gu, " ").trim();
+  const normalizedPromptLiteral = JSON.stringify(normalizedPrompt);
+  const inputSelectorsLiteral = JSON.stringify(INPUT_SELECTORS);
+  const stopSelectorsLiteral = JSON.stringify(STOP_BUTTON_SELECTORS);
+  const baselineLiteral =
+    typeof baselineTurns === "number" && Number.isFinite(baselineTurns)
+      ? Math.max(0, Math.floor(baselineTurns))
+      : -1;
+  const outcome = await Runtime.evaluate({
+    expression: `(() => {
+      const selectors = ${inputSelectorsLiteral};
+      const stopSelectors = ${stopSelectorsLiteral};
+      const normalize = (value) => String(value ?? '').replace(/\\s+/gu, ' ').trim();
+      const isVisible = (node) => {
+        if (!(node instanceof HTMLElement)) return false;
+        const rect = node.getBoundingClientRect();
+        return rect.width > 0 && rect.height > 0;
+      };
+      const readValue = (node) => {
+        if (node instanceof HTMLTextAreaElement || node instanceof HTMLInputElement) {
+          return node.value ?? '';
+        }
+        return node.innerText ?? node.textContent ?? '';
+      };
+      const candidates = selectors
+        .flatMap((selector) => Array.from(document.querySelectorAll(selector)))
+        .filter(isVisible);
+      const editor = candidates.find(
+        (node) => normalize(readValue(node)) === ${normalizedPromptLiteral},
+      ) ?? null;
+      const stopVisible = stopSelectors.some((selector) =>
+        Array.from(document.querySelectorAll(selector)).some(isVisible),
+      );
+      const turns = ${buildConversationTurnListExpression()};
+      const baseline = ${baselineLiteral};
+      const hasNewTurn = baseline >= 0 && turns.length > baseline;
+      if (!(editor instanceof HTMLElement) || stopVisible || hasNewTurn) {
+        return { staged: false, focused: false, stopVisible, hasNewTurn };
+      }
+      editor.focus();
+      return {
+        staged: true,
+        focused: document.activeElement === editor,
+        stopVisible,
+        hasNewTurn,
+      };
+    })()`,
+    returnByValue: true,
+  }).catch(() => null);
+  if (!outcome?.result?.value?.staged || !outcome.result.value.focused) {
+    return false;
+  }
+  logger("Send click left the prompt staged; submitting once via Enter");
+  await Input.dispatchKeyEvent({
+    type: "keyDown",
+    ...ENTER_KEY_EVENT,
+    text: ENTER_KEY_TEXT,
+    unmodifiedText: ENTER_KEY_TEXT,
+  });
+  await Input.dispatchKeyEvent({
+    type: "keyUp",
+    ...ENTER_KEY_EVENT,
+  });
+  return true;
 }
 
 export async function clearPromptComposer(Runtime: ChromeClient["Runtime"], logger: BrowserLogger) {
@@ -940,5 +1030,6 @@ function summarizeCommitProbe(probe: CommitProbeState): Record<string, unknown>
 export const __test__ = {
   attemptSendButton,
   sendButtonTimeoutMs,
+  submitStagedPromptViaEnter,
   verifyPromptCommitted,
 };
diff --git a/tests/browser/promptComposer.test.ts b/tests/browser/promptComposer.test.ts
index 6bd8edb11..3a4cf6d28 100644
--- a/tests/browser/promptComposer.test.ts
+++ b/tests/browser/promptComposer.test.ts
@@ -242,7 +242,7 @@ describe("promptComposer", () => {
     expect(promptComposer.sendButtonTimeoutMs(["oracle-attach-verify.txt"], 120_000)).toBe(120_000);
   });
 
-  test("marks prompt submitted before commit verification finishes", async () => {
+  test("marks prompt submitted after commit verification succeeds", async () => {
     const onPromptSubmitted = vi.fn();
     const runtime = {
       evaluate: vi.fn(async ({ expression }: { expression: string }) => {
@@ -260,6 +260,7 @@ describe("promptComposer", () => {
         if (expression.includes("button.scrollIntoView")) {
           return { result: { value: { status: "clicked" } } };
         }
+        expect(onPromptSubmitted).not.toHaveBeenCalled();
         return {
           result: {
             value: {
@@ -295,6 +296,71 @@ describe("promptComposer", () => {
     expect(onPromptSubmitted).toHaveBeenCalledTimes(1);
   });
 
+  test("uses Enter when a no-op click leaves a ProseMirror prompt staged with extra newlines", async () => {
+    vi.useFakeTimers();
+    try {
+      let focused = false;
+      class FakeHTMLElement {
+        innerText = "Line 1\n\n\nLine 2";
+        textContent = this.innerText;
+
+        getBoundingClientRect() {
+          return { width: 100, height: 30 };
+        }
+
+        focus() {
+          focused = true;
+        }
+      }
+      class FakeTextAreaElement extends FakeHTMLElement {
+        value = "";
+      }
+      class FakeInputElement extends FakeHTMLElement {
+        value = "";
+      }
+      const editor = new FakeHTMLElement();
+      const document = {
+        get activeElement() {
+          return focused ? editor : null;
+        },
+        querySelectorAll: (selector: string) =>
+          selector === "#prompt-textarea" || selector === ".ProseMirror" ? [editor] : [],
+      };
+      const runtime = {
+        evaluate: vi.fn(async ({ expression }: { expression: string }) => ({
+          result: {
+            value: Function(
+              "document",
+              "HTMLElement",
+              "HTMLTextAreaElement",
+              "HTMLInputElement",
+              `return ${expression};`,
+            )(document, FakeHTMLElement, FakeTextAreaElement, FakeInputElement),
+          },
+        })),
+      };
+      const input = { dispatchKeyEvent: vi.fn() };
+      const logger = Object.assign(vi.fn(), { verbose: false });
+
+      const result = promptComposer.submitStagedPromptViaEnter(
+        runtime as never,
+        input as never,
+        "Line 1\n\nLine 2",
+        0,
+        logger as never,
+      );
+      await vi.advanceTimersByTimeAsync(750);
+
+      await expect(result).resolves.toBe(true);
+      expect(input.dispatchKeyEvent).toHaveBeenCalledTimes(2);
+      expect(logger).toHaveBeenCalledWith(
+        "Send click left the prompt staged; submitting once via Enter",
+      );
+    } finally {
+      vi.useRealTimers();
+    }
+  });
+
   test("waits for a delayed trusted click without issuing a second send", async () => {
     vi.useFakeTimers();
     try {