diff --git a/pkg/cli/conversation.go b/pkg/cli/conversation.go
index 197e7b8..458da44 100644
--- a/pkg/cli/conversation.go
+++ b/pkg/cli/conversation.go
@@ -31,7 +31,7 @@ func (m *Message) FriendlyRole() string {
 
 func (c *Conversation) GenerateTitle() error {
 	const header = "Generate a consise 4-5 word title for the conversation below."
-	prompt := fmt.Sprintf("%s\n\n---\n\n%s", header, c.FormatForExternalPrompting())
+	prompt := fmt.Sprintf("%s\n\n---\n\n%s", header, c.FormatForExternalPrompting(false))
 
 	messages := []Message{
 		{
@@ -50,13 +50,16 @@ func (c *Conversation) GenerateTitle() error {
 	return nil
 }
 
-func (c *Conversation) FormatForExternalPrompting() string {
+func (c *Conversation) FormatForExternalPrompting(system bool) string {
 	sb := strings.Builder{}
 	messages, err := store.Messages(c)
 	if err != nil {
 		Fatal("Could not retrieve messages for conversation %v", c)
 	}
 	for _, message := range messages {
+		if message.Role == MessageRoleSystem && !system {
+			continue
+		}
 		sb.WriteString(fmt.Sprintf("<%s>\n", message.FriendlyRole()))
 		sb.WriteString(fmt.Sprintf("\"\"\"\n%s\n\"\"\"\n\n", message.OriginalContent))
 	}