diff --git a/static/js/emailLibrary.js b/static/js/emailLibrary.js
index 5f3473d0a..8a0826e0a 100644
--- a/static/js/emailLibrary.js
+++ b/static/js/emailLibrary.js
@@ -5923,8 +5923,8 @@ function _showAiReplyChoice(btn, em, data) {
   // Full = layered concentric circles to suggest "more, deeper" — not a fully
   // filled circle so it reads as a complement to the lightning, not as a "stop".
   menu.innerHTML = `
-    <div class="email-ai-reply-row" style="display:flex;flex-direction:column;gap:6px;min-width:180px;">
-      <div style="display:flex;align-items:center;gap:4px;">
+    <div class="email-ai-reply-row" data-step="choose" style="display:flex;flex-direction:column;gap:6px;min-width:180px;">
+      <div data-mode-row style="display:flex;align-items:center;gap:4px;">
         <button class="memory-toolbar-btn" data-mode="ai-reply-fast" title="Shorter, faster draft" style="display:inline-flex;align-items:center;gap:5px;">
           <svg width="11" height="11" viewBox="0 0 24 24" fill="var(--accent, var(--red))" aria-hidden="true"><polygon points="13 2 3 14 12 14 11 22 21 10 12 10 13 2"/></svg>
           Fast
@@ -5933,39 +5933,39 @@ function _showAiReplyChoice(btn, em, data) {
           <svg width="11" height="11" viewBox="0 0 24 24" fill="currentColor" aria-hidden="true" style="color:var(--accent, var(--red));"><circle cx="12" cy="12" r="6"/></svg>
           Full
         </button>
-        <button class="memory-toolbar-btn" data-act="note-toggle" title="Add a note about how to reply" style="display:inline-flex;align-items:center;justify-content:center;padding:4px 6px;line-height:1;margin-left:auto;">
-          <svg width="14" height="14" viewBox="0 0 24 24" fill="currentColor" aria-hidden="true"><circle cx="5" cy="12" r="2"/><circle cx="12" cy="12" r="2"/><circle cx="19" cy="12" r="2"/></svg>
-        </button>
       </div>
-      <div data-note-panel hidden>
-        <textarea data-note-input rows="2" placeholder="e.g. reply nicely but say no" style="width:100%;box-sizing:border-box;resize:vertical;min-height:38px;font-family:inherit;font-size:11px;padding:5px 6px;border-radius:5px;border:1px solid var(--border,#333);background:var(--bg-elev,#1a1a1a);color:var(--fg);"></textarea>
+      <div data-note-panel hidden style="display:flex;flex-direction:column;gap:6px;">
+        <textarea data-note-input rows="2" placeholder="Add context (optional)" style="width:100%;box-sizing:border-box;resize:vertical;min-height:42px;font-family:inherit;font-size:11px;padding:5px 6px;border-radius:5px;border:1px solid var(--border,#333);background:var(--bg-elev,#1a1a1a);color:var(--fg);"></textarea>
+        <button data-act="note-ok" class="memory-toolbar-btn" style="display:inline-flex;align-items:center;justify-content:center;gap:5px;">OK</button>
       </div>
     </div>
   `;
+  const modeRow = menu.querySelector('[data-mode-row]');
   const notePanel = menu.querySelector('[data-note-panel]');
   const noteInput = menu.querySelector('[data-note-input]');
-  menu.querySelector('[data-act="note-toggle"]').addEventListener('click', (ev) => {
-    ev.preventDefault();
-    ev.stopPropagation();
-    const opening = notePanel.hasAttribute('hidden');
-    if (opening) {
-      notePanel.removeAttribute('hidden');
-      setTimeout(() => noteInput.focus(), 0);
-    } else {
-      notePanel.setAttribute('hidden', '');
-    }
-  });
+  let pendingMode = null;
   menu.addEventListener('click', async (ev) => {
     const choice = ev.target.closest('[data-mode]');
-    if (!choice) return;
-    ev.preventDefault();
-    ev.stopPropagation();
-    const mode = choice.getAttribute('data-mode') || 'ai-reply';
-    // Always pick up whatever's in the textarea — empty = no note,
-    // typed = passed through as steering context.
-    const noteHint = (noteInput.value || '').trim();
-    _closeAiReplyChoice();
-    await _runAiReplyFromButton(btn, em, data, mode, noteHint);
+    if (choice) {
+      ev.preventDefault();
+      ev.stopPropagation();
+      // First click reveals the optional-context textarea; the actual
+      // draft runs on OK. Empty context just runs the chosen mode.
+      pendingMode = choice.getAttribute('data-mode') || 'ai-reply';
+      modeRow.setAttribute('hidden', '');
+      notePanel.removeAttribute('hidden');
+      setTimeout(() => noteInput.focus(), 0);
+      return;
+    }
+    const ok = ev.target.closest('[data-act="note-ok"]');
+    if (ok) {
+      ev.preventDefault();
+      ev.stopPropagation();
+      const noteHint = (noteInput.value || '').trim();
+      const mode = pendingMode || 'ai-reply';
+      _closeAiReplyChoice();
+      await _runAiReplyFromButton(btn, em, data, mode, noteHint);
+    }
   });
   // Esc closes the popover; ignore plain clicks inside the menu so the
   // textarea stays focused.