diff --git a/crates/goose-cli/src/session/mod.rs b/crates/goose-cli/src/session/mod.rs
index 6f09c1ee653d..9221f0610c6e 100644
--- a/crates/goose-cli/src/session/mod.rs
+++ b/crates/goose-cli/src/session/mod.rs
@@ -544,6 +544,10 @@ impl Session {
                         &Message::assistant().with_text("Chat context cleared."),
                         self.debug,
                     );
+                    if self.session_file.exists() {
+                        std::fs::remove_file(&self.session_file)?;
+                        std::fs::File::create(&self.session_file)?;
+                    }
                     continue;
                 }
                 input::InputResult::PromptCommand(opts) => {