diff --git a/crates/goose/src/agents/agent.rs b/crates/goose/src/agents/agent.rs
index e4134dd79d..93b28540ca 100644
--- a/crates/goose/src/agents/agent.rs
+++ b/crates/goose/src/agents/agent.rs
@@ -1638,6 +1638,7 @@ impl Agent {
                     session_manager.add_message(&session_config.id, msg).await?;
                 }
                 conversation.extend(messages_to_add);
+                conversation.sort_by_created();
                 if exit_chat {
                     break;
                 }
diff --git a/crates/goose/src/conversation/mod.rs b/crates/goose/src/conversation/mod.rs
index 9d2fe71496..480607c26c 100644
--- a/crates/goose/src/conversation/mod.rs
+++ b/crates/goose/src/conversation/mod.rs
@@ -103,6 +103,10 @@ impl Conversation {
         self.0.clear();
     }
 
+    pub fn sort_by_created(&mut self) {
+        self.0.sort_by_key(|m| m.created);
+    }
+
     pub fn filtered_messages<F>(&self, filter: F) -> Vec<Message>
     where
         F: Fn(&MessageMetadata) -> bool,
diff --git a/crates/goose/src/session/session_manager.rs b/crates/goose/src/session/session_manager.rs
index a11e4b1273..7d79a69e0f 100644
--- a/crates/goose/src/session/session_manager.rs
+++ b/crates/goose/src/session/session_manager.rs
@@ -1082,7 +1082,7 @@ impl SessionStorage {
     async fn get_conversation(&self, session_id: &str) -> Result<Conversation> {
         let pool = self.pool().await?;
         let rows = sqlx::query_as::<_, (String, String, i64, Option<String>, Option<String>)>(
-            "SELECT role, content_json, created_timestamp, metadata_json, message_id FROM messages WHERE session_id = ? ORDER BY timestamp",
+            "SELECT role, content_json, created_timestamp, metadata_json, message_id FROM messages WHERE session_id = ? ORDER BY created_timestamp",
         )
             .bind(session_id)
             .fetch_all(pool)