diff --git a/blueprints/scheduled_messages/__init__.py b/blueprints/scheduled_messages/__init__.py
index 96f0bfd..10a921e 100644
--- a/blueprints/scheduled_messages/__init__.py
+++ b/blueprints/scheduled_messages/__init__.py
@@ -23,6 +23,7 @@ def _serialize(msg: ScheduledMessage) -> dict:
         "scheduled_at": msg.scheduled_at.isoformat(),
         "status": msg.status.value,
         "recurrence": msg.recurrence.value,
+        "use_agent": msg.use_agent,
         "error_message": msg.error_message,
         "created_at": msg.created_at.isoformat(),
         "updated_at": msg.updated_at.isoformat(),
@@ -89,6 +90,8 @@ async def create_message():
 
     user_id = get_jwt_identity()
 
+    use_agent = bool(data.get("use_agent", False))
+
     msg = await ScheduledMessage.create(
         recipient=recipient,
         channel=channel_enum,
@@ -96,6 +99,7 @@ async def create_message():
         subject=subject,
         scheduled_at=scheduled_at,
         recurrence=recurrence_enum,
+        use_agent=use_agent,
         created_by_id=user_id,
     )
     return jsonify(_serialize(msg)), 201
@@ -131,6 +135,8 @@ async def update_message(msg_id: str):
             msg.recurrence = Recurrence(data["recurrence"])
         except ValueError:
             return jsonify({"error": f"Invalid recurrence: {data['recurrence']}"}), 400
+    if "use_agent" in data:
+        msg.use_agent = bool(data["use_agent"])
     if "scheduled_at" in data:
         try:
             scheduled_at = datetime.fromisoformat(data["scheduled_at"])
diff --git a/blueprints/scheduled_messages/models.py b/blueprints/scheduled_messages/models.py
index f1a02f3..0be6081 100644
--- a/blueprints/scheduled_messages/models.py
+++ b/blueprints/scheduled_messages/models.py
@@ -36,6 +36,7 @@ class ScheduledMessage(Model):
     recurrence = fields.CharEnumField(
         enum_type=Recurrence, max_length=20, default=Recurrence.NONE
     )
+    use_agent = fields.BooleanField(default=False)
     error_message = fields.TextField(null=True)
     created_by = fields.ForeignKeyField(
         "models.User", related_name="scheduled_messages"
diff --git a/blueprints/scheduled_messages/scheduler.py b/blueprints/scheduled_messages/scheduler.py
index 54c177b..4e3da45 100644
--- a/blueprints/scheduled_messages/scheduler.py
+++ b/blueprints/scheduled_messages/scheduler.py
@@ -16,6 +16,19 @@ RECURRENCE_DELTAS = {
 }
 
 
+async def _run_agent(prompt: str) -> str:
+    """Run a prompt through the LangChain agent and return the response text."""
+    from blueprints.conversation.agents import main_agent
+    from blueprints.conversation.prompts import SIMBA_SYSTEM_PROMPT
+
+    messages_payload = [
+        {"role": "system", "content": SIMBA_SYSTEM_PROMPT},
+        {"role": "user", "content": prompt},
+    ]
+    response = await main_agent.ainvoke({"messages": messages_payload})
+    return response.get("messages", [])[-1].content
+
+
 async def _schedule_next_occurrence(msg: ScheduledMessage):
     """Create the next pending occurrence for a recurring message."""
     delta = RECURRENCE_DELTAS.get(msg.recurrence)
@@ -35,6 +48,7 @@ async def _schedule_next_occurrence(msg: ScheduledMessage):
         subject=msg.subject,
         scheduled_at=next_at,
         recurrence=msg.recurrence,
+        use_agent=msg.use_agent,
         created_by_id=msg.created_by_id,
     )
     logger.info(
@@ -56,11 +70,16 @@ async def scheduled_messages_loop():
 
             for msg in due:
                 try:
+                    send_content = msg.content
+
+                    if msg.use_agent:
+                        send_content = await _run_agent(msg.content)
+
                     if msg.channel == MessageChannel.IMESSAGE:
                         from blueprints.imessage import send_imessage
                         from utils.strip_markdown import strip_markdown
 
-                        await send_imessage(msg.recipient, strip_markdown(msg.content))
+                        await send_imessage(msg.recipient, strip_markdown(send_content))
 
                     elif msg.channel == MessageChannel.EMAIL:
                         from blueprints.email import send_email_reply
@@ -68,7 +87,7 @@ async def scheduled_messages_loop():
                         await send_email_reply(
                             to=msg.recipient,
                             subject=msg.subject or "(no subject)",
-                            body=msg.content,
+                            body=send_content,
                         )
 
                     msg.status = MessageStatus.SENT
diff --git a/raggr-frontend/src/api/scheduledMessageService.ts b/raggr-frontend/src/api/scheduledMessageService.ts
index 45173da..e015cc4 100644
--- a/raggr-frontend/src/api/scheduledMessageService.ts
+++ b/raggr-frontend/src/api/scheduledMessageService.ts
@@ -9,6 +9,7 @@ export interface ScheduledMessage {
   scheduled_at: string;
   status: "pending" | "sent" | "failed" | "cancelled";
   recurrence: "none" | "daily" | "weekly" | "monthly";
+  use_agent: boolean;
   error_message: string | null;
   created_at: string;
   updated_at: string;
@@ -21,6 +22,7 @@ export interface CreateScheduledMessage {
   subject?: string;
   scheduled_at: string;
   recurrence?: "none" | "daily" | "weekly" | "monthly";
+  use_agent?: boolean;
 }
 
 class ScheduledMessageService {
diff --git a/raggr-frontend/src/components/ScheduledMessagesPanel.tsx b/raggr-frontend/src/components/ScheduledMessagesPanel.tsx
index 3fad381..2396d8f 100644
--- a/raggr-frontend/src/components/ScheduledMessagesPanel.tsx
+++ b/raggr-frontend/src/components/ScheduledMessagesPanel.tsx
@@ -1,5 +1,5 @@
 import { useState } from "react";
-import { X, Clock, Send, Trash2, XCircle, RotateCcw, Repeat } from "lucide-react";
+import { X, Clock, Send, Trash2, XCircle, RotateCcw, Repeat, Bot } from "lucide-react";
 import { cn } from "../lib/utils";
 import { Button } from "./ui/button";
 import { Input } from "./ui/input";
@@ -37,6 +37,7 @@ export const ScheduledMessagesPanel = ({ onClose }: Props) => {
   const [content, setContent] = useState("");
   const [scheduledAt, setScheduledAt] = useState("");
   const [recurrence, setRecurrence] = useState<"none" | "daily" | "weekly" | "monthly">("none");
+  const [useAgent, setUseAgent] = useState(false);
   const [error, setError] = useState("");
   const [submitting, setSubmitting] = useState(false);
 
@@ -59,6 +60,7 @@ export const ScheduledMessagesPanel = ({ onClose }: Props) => {
         content,
         scheduled_at: new Date(scheduledAt).toISOString(),
         recurrence,
+        use_agent: useAgent,
       };
       if (channel === "email") data.subject = subject;
       await scheduledMessageService.create(data);
@@ -67,6 +69,7 @@ export const ScheduledMessagesPanel = ({ onClose }: Props) => {
       setContent("");
       setScheduledAt("");
       setRecurrence("none");
+      setUseAgent(false);
       refresh();
     } catch (err) {
       setError(err instanceof Error ? err.message : "Failed to schedule message");
@@ -189,6 +192,24 @@ export const ScheduledMessagesPanel = ({ onClose }: Props) => {
               ))}
             </div>
 
+            <div className="flex items-center gap-2">
+              <button
+                onClick={() => setUseAgent(!useAgent)}
+                className={cn(
+                  "flex items-center gap-1.5 px-3 py-1.5 rounded-lg text-xs font-medium transition-colors cursor-pointer",
+                  useAgent
+                    ? "bg-leaf-pale text-leaf-dark"
+                    : "bg-sand-light/40 text-warm-gray hover:text-charcoal",
+                )}
+              >
+                <Bot size={12} />
+                Ask Simba
+              </button>
+              <span className="text-xs text-warm-gray">
+                {useAgent ? "Content is a prompt — Simba's response will be sent" : "Content sent as-is"}
+              </span>
+            </div>
+
             {channel === "email" && (
               <Input
                 value={subject}
@@ -200,7 +221,7 @@ export const ScheduledMessagesPanel = ({ onClose }: Props) => {
             <textarea
               value={content}
               onChange={(e) => setContent(e.target.value)}
-              placeholder="Message content..."
+              placeholder={useAgent ? "Enter a prompt for Simba..." : "Message content..."}
               rows={3}
               className="w-full rounded-xl border border-sand bg-cream-light px-3 py-2 text-sm text-charcoal placeholder:text-warm-gray/50 focus:outline-none focus:ring-2 focus:ring-leaf/30 resize-none"
             />
@@ -249,10 +270,15 @@ export const ScheduledMessagesPanel = ({ onClose }: Props) => {
                     <TableCell className="text-xs truncate max-w-[140px]" title={msg.recipient}>
                       {msg.recipient}
                     </TableCell>
-                    <TableCell className="text-xs truncate max-w-[180px]" title={msg.content}>
-                      {msg.content.length > 60
-                        ? msg.content.slice(0, 60) + "..."
-                        : msg.content}
+                    <TableCell className="text-xs max-w-[180px]" title={msg.content}>
+                      <div className="flex items-center gap-1">
+                        {msg.use_agent && <Bot size={10} className="text-leaf-dark shrink-0" />}
+                        <span className="truncate">
+                          {msg.content.length > 60
+                            ? msg.content.slice(0, 60) + "..."
+                            : msg.content}
+                        </span>
+                      </div>
                     </TableCell>
                     <TableCell className="text-xs text-warm-gray">
                       {new Date(msg.scheduled_at).toLocaleString()}