diff --git a/routes/email_routes.py b/routes/email_routes.py
index 11e1c3255..0a4c2c5a1 100644
--- a/routes/email_routes.py
+++ b/routes/email_routes.py
@@ -2657,11 +2657,15 @@ def setup_email_routes():
             source_uid = (data.get("uid") or "").strip()
             source_folder = (data.get("folder") or "INBOX").strip()
             fast_reply = bool(data.get("fast", False))
+            user_hint = (data.get("user_hint") or "").strip()
 
             if not original_body:
                 return {"success": False, "error": "No email body provided"}
 
-            if message_id:
+            # Skip cache lookup when the caller supplied a user_hint — the
+            # cached generic reply doesn't reflect the instructions and
+            # would silently override them.
+            if message_id and not user_hint:
                 try:
                     _c = _sql3.connect(SCHEDULED_DB)
                     owner_clause, owner_params = _email_cache_owner_clause(owner)
@@ -2801,8 +2805,13 @@ def setup_email_routes():
             user_msg = (
                 f"Recipient: {to}\nSubject: {subject}\n\n"
                 f"Original email and any current draft:\n{original_body[:6000]}\n\n"
-                f"Draft a reply. Return only the reply body text."
             )
+            if user_hint:
+                user_msg += (
+                    f"User's instructions for THIS reply (follow these — they override "
+                    f"defaults like length/tone):\n{user_hint[:2000]}\n\n"
+                )
+            user_msg += "Draft a reply. Return only the reply body text."
 
             # Build a candidate chain so a stale session-stored API key
             # (the most common cause of "authentication failed" here)
diff --git a/static/js/emailInbox.js b/static/js/emailInbox.js
index 6278574d1..b07469316 100644
--- a/static/js/emailInbox.js
+++ b/static/js/emailInbox.js
@@ -118,7 +118,7 @@ export function init(documentModule) {
       } catch (_) {}
       if (opts.compose) { _composeNew(); return; }
       if (opts.email) {
-        await _openEmail(opts.email, null, opts.emailData, opts.mode || 'reply');
+        await _openEmail(opts.email, null, opts.emailData, opts.mode || 'reply', opts.noteHint || '');
       }
     },
   });
@@ -630,7 +630,7 @@ function _createEmailItem(em) {
   return item;
 }
 
-async function _openEmail(em, itemEl, preloadedData = null, mode = 'reply') {
+async function _openEmail(em, itemEl, preloadedData = null, mode = 'reply', noteHint = '') {
   const aiReplyMode = mode === 'ai-reply-fast' ? 'fast' : (mode === 'ai-reply-full' ? 'full' : '');
   const wantsAiReply = mode === 'ai-reply' || !!aiReplyMode;
   let aiSuggestedBody = null;
@@ -690,6 +690,7 @@ async function _openEmail(em, itemEl, preloadedData = null, mode = 'reply') {
               uid: String(em.uid || ''),
               folder: _currentFolder,
               fast: aiReplyMode ? aiReplyMode === 'fast' : _shouldUseFastAiReply(data),
+              user_hint: (noteHint || '').trim() || undefined,
             }),
           });
           const result = await res.json();