diff --git a/crates/goose/src/agents/agent.rs b/crates/goose/src/agents/agent.rs
index 3f32950166..36c179fed3 100644
--- a/crates/goose/src/agents/agent.rs
+++ b/crates/goose/src/agents/agent.rs
@@ -1533,6 +1533,11 @@ impl Agent {
                                 Err(e) => {
                                     crate::posthog::emit_error("compaction_failed", &e.to_string());
                                     error!("Compaction failed: {}", e);
+                                    yield AgentEvent::Message(
+                                        Message::assistant().with_text(
+                                            format!("Ran into this error trying to compact: {e}.\n\nPlease try again or create a new session")
+                                        )
+                                    );
                                     break;
                                 }
                             }