diff --git a/src/data/guest-messages.json b/src/data/guest-messages.json
new file mode 100644
index 0000000..a53a612
--- /dev/null
+++ b/src/data/guest-messages.json
@@ -0,0 +1,68 @@
+{
+  "conversations": [
+    {
+      "id": "conv-001",
+      "propertyId": "prop-001",
+      "propertyName": "Oceanfront Villa",
+      "guestName": "Alice Johnson",
+      "guestEmail": "alice@email.com",
+      "status": "pending",
+      "messages": [
+        {
+          "id": "msg-001",
+          "from": "guest",
+          "timestamp": "2024-01-15T10:30:00Z",
+          "content": "Hi! I'm interested in booking your villa for my family vacation. We're a family of 4 with two young kids. Is the property child-friendly? Also, is there beach access?"
+        }
+      ]
+    },
+    {
+      "id": "conv-002",
+      "propertyId": "prop-002",
+      "propertyName": "Downtown Loft",
+      "guestName": "Bob Williams",
+      "guestEmail": "bob@email.com",
+      "status": "pending",
+      "messages": [
+        {
+          "id": "msg-002",
+          "from": "guest",
+          "timestamp": "2024-01-16T14:20:00Z",
+          "content": "Hello, I'm looking to book for a business trip next month. Do you have a desk and reliable WiFi? I'll need to work during my stay."
+        }
+      ]
+    },
+    {
+      "id": "conv-003",
+      "propertyId": "prop-003",
+      "propertyName": "Mountain Cabin",
+      "guestName": "Carol Davis",
+      "guestEmail": "carol@email.com",
+      "status": "pending",
+      "messages": [
+        {
+          "id": "msg-003",
+          "from": "guest",
+          "timestamp": "2024-01-17T09:15:00Z",
+          "content": "We're planning a romantic getaway for our anniversary. Does the cabin have a hot tub? And are there any good restaurants nearby you'd recommend?"
+        }
+      ]
+    },
+    {
+      "id": "conv-004",
+      "propertyId": "prop-001",
+      "propertyName": "Oceanfront Villa",
+      "guestName": "David Martinez",
+      "guestEmail": "david@email.com",
+      "status": "pending",
+      "messages": [
+        {
+          "id": "msg-004",
+          "from": "guest",
+          "timestamp": "2024-01-18T16:45:00Z",
+          "content": "Quick question - what's your cancellation policy? I might need to change my dates depending on work."
+        }
+      ]
+    }
+  ]
+}
diff --git a/src/routes/suggestions.ts b/src/routes/suggestions.ts
new file mode 100644
index 0000000..5891a75
--- /dev/null
+++ b/src/routes/suggestions.ts
@@ -0,0 +1,175 @@
+import { Router, Request, Response } from 'express';
+import { z } from 'zod';
+import * as fs from 'fs';
+import * as path from 'path';
+
+const router = Router();
+
+interface Message {
+  id: string;
+  from: 'guest' | 'host';
+  timestamp: string;
+  content: string;
+}
+
+interface Conversation {
+  id: string;
+  propertyId: string;
+  propertyName: string;
+  guestName: string;
+  guestEmail: string;
+  status: string;
+  messages: Message[];
+}
+
+interface ConversationDatabase {
+  conversations: Conversation[];
+}
+
+function loadConversations(): ConversationDatabase {
+  const dataPath = path.join(__dirname, '../data/guest-messages.json');
+  return JSON.parse(fs.readFileSync(dataPath, 'utf-8'));
+}
+
+const suggestionsQuerySchema = z.object({
+  conversationId: z.string(),
+  model: z.string().optional(),
+});
+
+const LITELLM_SERVER_URL = process.env.LITELLM_SERVER_URL || 'http://localhost:4000';
+
+async function generateReplySuggestions(
+  conversation: Conversation,
+  model?: string
+): Promise<string[]> {
+  // Get the last guest message
+  const guestMessages = conversation.messages.filter((m) => m.from === 'guest');
+  const lastGuestMessage = guestMessages[guestMessages.length - 1];
+
+  if (!lastGuestMessage) {
+    throw new Error('No guest message found in conversation');
+  }
+
+  const systemPrompt = `You are a helpful assistant for vacation rental hosts. Generate professional, friendly reply suggestions for guest inquiries.
+
+Property: ${conversation.propertyName}
+Guest Name: ${conversation.guestName}
+
+Generate exactly 3 reply suggestions that are:
+- Professional and welcoming
+- Address the guest's specific questions
+- Encourage booking while being honest
+- Appropriately brief (2-4 sentences each)
+
+Format your response as a JSON array of 3 strings, like:
+["Reply 1", "Reply 2", "Reply 3"]`;
+
+  const userPrompt = `Guest Message:
+"""
+${lastGuestMessage.content}
+"""
+
+Generate 3 professional reply suggestions for this message.`;
+
+  const response = await fetch(`${LITELLM_SERVER_URL}/v1/chat/completions`, {
+    method: 'POST',
+    headers: { 'Content-Type': 'application/json' },
+    body: JSON.stringify({
+      model: model || 'gpt-4o-mini',
+      messages: [
+        { role: 'system', content: systemPrompt },
+        { role: 'user', content: userPrompt },
+      ],
+    }),
+  });
+
+  if (!response.ok) {
+    throw new Error(`LiteLLM request failed: ${await response.text()}`);
+  }
+
+  const data: any = await response.json();
+  const content = data.choices[0].message.content;
+
+  // Try to parse as JSON array
+  try {
+    // Handle markdown code blocks
+    let jsonContent = content;
+    if (jsonContent.includes('```json')) {
+      jsonContent = jsonContent.replace(/```json\n?/g, '').replace(/```\n?/g, '');
+    } else if (jsonContent.includes('```')) {
+      jsonContent = jsonContent.replace(/```\n?/g, '');
+    }
+
+    const suggestions = JSON.parse(jsonContent.trim());
+    if (Array.isArray(suggestions)) {
+      return suggestions.slice(0, 3);
+    }
+  } catch {
+    // If not valid JSON, split by newlines or return as single suggestion
+    return [content];
+  }
+
+  return [content];
+}
+
+// Generate reply suggestions for a conversation
+router.post('/authorized/:level/suggestions/generate', async (req: Request, res: Response) => {
+  try {
+    const { level } = req.params as { level: 'minnow' | 'shark' };
+    const { conversationId, model } = suggestionsQuerySchema.parse(req.body);
+
+    const database = loadConversations();
+    const conversation = database.conversations.find((c) => c.id === conversationId);
+
+    if (!conversation) {
+      return res.status(404).json({
+        error: 'Conversation not found',
+        message: `No conversation found with ID: ${conversationId}`,
+      });
+    }
+
+    const suggestions = await generateReplySuggestions(conversation, model);
+
+    return res.json({
+      conversationId,
+      propertyName: conversation.propertyName,
+      guestName: conversation.guestName,
+      suggestions,
+    });
+  } catch (error) {
+    if (error instanceof z.ZodError) {
+      return res.status(400).json({ error: 'Validation error', details: error.errors });
+    }
+    console.error('Suggestions generation error:', error);
+    return res.status(500).json({
+      error: 'Internal server error',
+      message: error instanceof Error ? error.message : 'Unknown error',
+    });
+  }
+});
+
+// List conversations endpoint
+router.get('/authorized/:level/suggestions/conversations', async (req: Request, res: Response) => {
+  try {
+    const database = loadConversations();
+
+    return res.json({
+      conversations: database.conversations.map((c) => ({
+        id: c.id,
+        propertyName: c.propertyName,
+        guestName: c.guestName,
+        status: c.status,
+        messageCount: c.messages.length,
+        lastMessageAt: c.messages[c.messages.length - 1]?.timestamp,
+      })),
+    });
+  } catch (error) {
+    console.error('Conversations list error:', error);
+    return res.status(500).json({
+      error: 'Internal server error',
+      message: error instanceof Error ? error.message : 'Unknown error',
+    });
+  }
+});
+
+export default router;
diff --git a/src/server.ts b/src/server.ts
index bf8fc7f..26994d5 100644
--- a/src/server.ts
+++ b/src/server.ts
@@ -7,6 +7,7 @@ import { chatHandler } from './routes/chat';
 import { tokenHandler, jwksHandler } from './routes/oauth';
 import { generateRSAKeyPair } from './utils/jwt-keys';
 import { authenticateToken } from './middleware/auth';
+import suggestionsRouter from './routes/suggestions';
 
 // Initialize OAuth key pair on startup
 generateRSAKeyPair();
@@ -31,6 +32,9 @@ app.get('/health', (req: Request, res: Response) => {
 app.post('/:level/chat', chatHandler);
 app.post('/authorized/:level/chat', authenticateToken, chatHandler);
 
+// Smart reply suggestions endpoints
+app.use(suggestionsRouter);
+
 // OAuth endpoints
 app.post('/oauth/token', tokenHandler);
 app.get('/.well-known/jwks.json', jwksHandler);