diff --git a/crates/goose-cli/src/session/mod.rs b/crates/goose-cli/src/session/mod.rs
index a7678327b731..4bee1f987f27 100644
--- a/crates/goose-cli/src/session/mod.rs
+++ b/crates/goose-cli/src/session/mod.rs
@@ -1302,6 +1302,7 @@ impl CliSession {
                 Ok(messages) => {
                     let start_len = self.messages.len();
                     let mut valid = true;
+                    let num_messages = messages.len();
                     for (i, prompt_message) in messages.into_iter().enumerate() {
                         let msg = Message::from(prompt_message);
                         // ensure we get a User - Assistant - User type pattern
@@ -1329,6 +1330,17 @@ impl CliSession {
                     }
 
                     if valid {
+                        if num_messages > 1 {
+                            for i in 0..(num_messages - 1) {
+                                let msg = &self.messages.messages()[start_len + i];
+                                self.agent
+                                    .config
+                                    .session_manager
+                                    .add_message(&self.session_id, msg)
+                                    .await?;
+                            }
+                        }
+
                         output::show_thinking();
                         self.process_agent_response(true, CancellationToken::default())
                             .await?;