diff --git a/crates/goose-cli/src/session/mod.rs b/crates/goose-cli/src/session/mod.rs
index bf0f258504..da5af1544b 100644
--- a/crates/goose-cli/src/session/mod.rs
+++ b/crates/goose-cli/src/session/mod.rs
@@ -122,6 +122,21 @@ impl Session {
         }
     }
 
+    /// Helper function to summarize context messages
+    async fn summarize_context_messages(
+        messages: &mut Vec<Message>,
+        agent: &Agent,
+        message_suffix: &str,
+    ) -> Result<()> {
+        // Summarize messages to fit within context length
+        let (summarized_messages, _) = agent.summarize_context(messages).await?;
+        let msg = format!("Context maxed out\n{}\n{}", "-".repeat(50), message_suffix);
+        output::render_text(&msg, Some(Color::Yellow), true);
+        *messages = summarized_messages;
+
+        Ok(())
+    }
+
     /// Add a stdio extension to the session
     ///
     /// # Arguments
@@ -703,39 +718,43 @@ impl Session {
                             } else if let Some(MessageContent::ContextLengthExceeded(_)) = message.content.first() {
                                 output::hide_thinking();
 
-                                let prompt = "The model's context length is maxed out. You will need to reduce the # msgs. Do you want to?".to_string();
-                                let selected = cliclack::select(prompt)
-                                    .item("clear", "Clear Session", "Removes all messages from Goose's memory")
-                                    .item("truncate", "Truncate Messages", "Removes old messages till context is within limits")
-                                    .item("summarize", "Summarize Session", "Summarize the session to reduce context length")
-                                    .interact()?;
+                                if interactive {
+                                    // In interactive mode, ask the user what to do
+                                    let prompt = "The model's context length is maxed out. You will need to reduce the # msgs. Do you want to?".to_string();
+                                    let selected = cliclack::select(prompt)
+                                        .item("clear", "Clear Session", "Removes all messages from Goose's memory")
+                                        .item("truncate", "Truncate Messages", "Removes old messages till context is within limits")
+                                        .item("summarize", "Summarize Session", "Summarize the session to reduce context length")
+                                        .interact()?;
 
-                                match selected {
-                                    "clear" => {
-                                        self.messages.clear();
-                                        let msg = format!("Session cleared.\n{}", "-".repeat(50));
-                                        output::render_text(&msg, Some(Color::Yellow), true);
-                                        break;  // exit the loop to hand back control to the user
-                                    }
-                                    "truncate" => {
-                                        // Truncate messages to fit within context length
-                                        let (truncated_messages, _) = self.agent.truncate_context(&self.messages).await?;
-                                        let msg = format!("Context maxed out\n{}\nGoose tried its best to truncate messages for you.", "-".repeat(50));
-                                        output::render_text("", Some(Color::Yellow), true);
-                                        output::render_text(&msg, Some(Color::Yellow), true);
-                                        self.messages = truncated_messages;
-                                    }
-                                    "summarize" => {
-                                        // Summarize messages to fit within context length
-                                        let (summarized_messages, _) = self.agent.summarize_context(&self.messages).await?;
-                                        let msg = format!("Context maxed out\n{}\nGoose summarized messages for you.", "-".repeat(50));
-                                        output::render_text(&msg, Some(Color::Yellow), true);
-                                        self.messages = summarized_messages;
-                                    }
-                                    _ => {
-                                        unreachable!()
+                                    match selected {
+                                        "clear" => {
+                                            self.messages.clear();
+                                            let msg = format!("Session cleared.\n{}", "-".repeat(50));
+                                            output::render_text(&msg, Some(Color::Yellow), true);
+                                            break;  // exit the loop to hand back control to the user
+                                        }
+                                        "truncate" => {
+                                            // Truncate messages to fit within context length
+                                            let (truncated_messages, _) = self.agent.truncate_context(&self.messages).await?;
+                                            let msg = format!("Context maxed out\n{}\nGoose tried its best to truncate messages for you.", "-".repeat(50));
+                                            output::render_text("", Some(Color::Yellow), true);
+                                            output::render_text(&msg, Some(Color::Yellow), true);
+                                            self.messages = truncated_messages;
+                                        }
+                                        "summarize" => {
+                                            // Use the helper function to summarize context
+                                            Self::summarize_context_messages(&mut self.messages, &self.agent, "Goose summarized messages for you.").await?;
+                                        }
+                                        _ => {
+                                            unreachable!()
+                                        }
                                     }
+                                } else {
+                                    // In headless mode (goose run), automatically use summarize
+                                    Self::summarize_context_messages(&mut self.messages, &self.agent, "Goose automatically summarized messages to continue processing.").await?;
                                 }
+
                                 // Restart the stream after handling ContextLengthExceeded
                                 stream = self
                                     .agent