diff --git a/pkg/cmd/util/util.go b/pkg/cmd/util/util.go
index 7c4b962..84d3178 100644
--- a/pkg/cmd/util/util.go
+++ b/pkg/cmd/util/util.go
@@ -2,6 +2,7 @@ package util
 
 import (
 	"context"
+	"encoding/json"
 	"fmt"
 	"os"
 	"strings"
@@ -149,36 +150,40 @@ func FormatForExternalPrompt(messages []model.Message, system bool) string {
 }
 
 func GenerateTitle(ctx *lmcli.Context, messages []model.Message) (string, error) {
-	const prompt = `Above is an excerpt from a conversation between a user and AI assistant.
-
-Reply with a short title (no more than 8 words) that reflects the topic of the conversation, read from the user's perspective.
+	const systemPrompt = `You will be shown a conversation between a user and an AI assistant. Your task is to generate a short title (8 words or less) for the provided conversation that reflects the conversation's topic.
 
 Example conversation:
 
-"""
-User:
+[{"role": "user", "content": "Can you help me with my math homework?"},{"role": "assistant", "content": "Sure, what topic are you struggling with?"}]
 
-  Hello!
+Your response (response only with JSON in the format shown):
 
-Assistant:
-
-  Hello! How may I assist you?
-"""
-
-Your response:
-
-"""
-Title: A brief introduction
-"""
-
-Respond only as shown above.
+{"title": "Help with math homework"}
 `
-	conversation := FormatForExternalPrompt(messages, false)
+	type msg struct {
+		Role    string
+		Content string
+	}
+
+	var msgs []msg
+	for _, m := range messages {
+		msgs = append(msgs, msg{string(m.Role), m.Content})
+	}
+
+	// Serialize the conversation to JSON
+	conversation, err := json.Marshal(msgs)
+	if err != nil {
+		return "", err
+	}
 
 	generateRequest := []model.Message{
+		{
+			Role:    model.MessageRoleSystem,
+			Content: systemPrompt,
+		},
 		{
 			Role:    model.MessageRoleUser,
-			Content: fmt.Sprintf("\"\"\"\n%s\n\"\"\"\n\n%s", conversation, prompt),
+			Content: string(conversation),
 		},
 	}
 
@@ -197,12 +202,16 @@ Respond only as shown above.
 		return "", err
 	}
 
-	// TODO: validate response format
-	response = strings.TrimPrefix(response, "Title:")
-	response = strings.TrimSpace(response)
-	response = strings.Trim(response, "\"")
+	// Parse the JSON response
+	var jsonResponse struct {
+		Title string `json:"title"`
+	}
+	err = json.Unmarshal([]byte(response), &jsonResponse)
+	if err != nil {
+		return "", err
+	}
 
-	return response, nil
+	return jsonResponse.Title, nil
 }
 
 // ShowWaitAnimation prints an animated ellipses to stdout until something is