diff --git a/src/agent.rs b/src/agent.rs
index b6bf3d7..9362f4d 100644
--- a/src/agent.rs
+++ b/src/agent.rs
@@ -473,13 +473,18 @@ async fn agent_loop(
 
                     // Prepare state for execution: set first pending step to Running
                     if let Some(next) = state.first_actionable_step() {
+                        let was_same_step = matches!(state.phase, AgentPhase::Executing { step } if step == next);
                         if let Some(step) = state.steps.iter_mut().find(|s| s.order == next) {
                             if matches!(step.status, StepStatus::Pending) {
                                 step.status = StepStatus::Running;
                             }
                         }
                         state.phase = AgentPhase::Executing { step: next };
-                        state.current_step_chat_history.clear();
+                        // Only clear chat history when advancing to a new step;
+                        // keep it when resuming the same step after wait_for_approval
+                        if !was_same_step {
+                            state.current_step_chat_history.clear();
+                        }
                     }
 
                     let instructions = read_instructions(&workdir).await;