diff --git a/codex-rs/core/src/codex.rs b/codex-rs/core/src/codex.rs
index faab4a8c2b..db70d82cc9 100644
--- a/codex-rs/core/src/codex.rs
+++ b/codex-rs/core/src/codex.rs
@@ -1846,34 +1846,113 @@ impl Session {
     fn reconstruct_turn_context_history_from_rollout(
         rollout_items: &[RolloutItem],
     ) -> Vec<Option<TurnContextItem>> {
-        let mut history = Vec::new();
+        let mut history_items = Vec::new();
         let mut awaiting_turn_context = false;
+        let mut turn_context_history = Vec::new();
         for item in rollout_items {
             match item {
-                RolloutItem::ResponseItem(ResponseItem::Message { role, .. }) if role == "user" => {
-                    history.push(None);
-                    awaiting_turn_context = true;
+                RolloutItem::ResponseItem(response_item) => {
+                    history_items.push(response_item.clone());
+                    if matches!(response_item, ResponseItem::Message { role, .. } if role == "user")
+                    {
+                        turn_context_history.push(None);
+                        awaiting_turn_context = true;
+                    }
                 }
                 RolloutItem::TurnContext(ctx) => {
                     if awaiting_turn_context {
-                        if let Some(last) = history.last_mut() {
+                        if let Some(last) = turn_context_history.last_mut() {
                             *last = Some(ctx.clone());
                         } else {
-                            history.push(Some(ctx.clone()));
+                            turn_context_history.push(Some(ctx.clone()));
                         }
                         awaiting_turn_context = false;
                     }
                 }
+                RolloutItem::Compacted(compacted) => {
+                    if let Some(replacement) = &compacted.replacement_history {
+                        history_items = replacement.clone();
+                        // Remote compaction can reorder messages, so drop contexts to avoid
+                        // misalignment.
+                        turn_context_history = vec![None; Session::user_turn_count(&history_items)];
+                    } else {
+                        let user_messages = collect_user_messages(&history_items);
+                        history_items = compact::build_compacted_history(
+                            Vec::new(),
+                            &user_messages,
+                            &compacted.message,
+                        );
+                        turn_context_history = Self::rebuild_turn_context_history_after_compaction(
+                            turn_context_history,
+                            &history_items,
+                        );
+                    }
+                    awaiting_turn_context = false;
+                }
                 RolloutItem::EventMsg(EventMsg::ThreadRolledBack(rollback)) => {
+                    Self::drop_last_n_user_turns_from_items(&mut history_items, rollback.num_turns);
                     let drop = usize::try_from(rollback.num_turns).unwrap_or(usize::MAX);
-                    let new_len = history.len().saturating_sub(drop);
-                    history.truncate(new_len);
+                    let new_len = turn_context_history.len().saturating_sub(drop);
+                    turn_context_history.truncate(new_len);
                     awaiting_turn_context = false;
                 }
                 _ => {}
             }
         }
-        history
+        turn_context_history
+    }
+
+    fn rebuild_turn_context_history_after_compaction(
+        previous: Vec<Option<TurnContextItem>>,
+        compacted_history: &[ResponseItem],
+    ) -> Vec<Option<TurnContextItem>> {
+        let user_messages = collect_user_messages(compacted_history);
+        let retained = user_messages.len();
+        let mut updated = Self::take_last_with_padding(previous, retained);
+        updated.push(None);
+        updated
+    }
+
+    fn take_last_with_padding(
+        mut history: Vec<Option<TurnContextItem>>,
+        retained: usize,
+    ) -> Vec<Option<TurnContextItem>> {
+        if retained == 0 {
+            return Vec::new();
+        }
+        if history.len() >= retained {
+            history.split_off(history.len() - retained)
+        } else {
+            let mut padded = Vec::with_capacity(retained);
+            padded.resize_with(retained - history.len(), || None);
+            padded.append(&mut history);
+            padded
+        }
+    }
+
+    fn drop_last_n_user_turns_from_items(items: &mut Vec<ResponseItem>, num_turns: u32) {
+        if num_turns == 0 {
+            return;
+        }
+
+        let user_positions: Vec<usize> = items
+            .iter()
+            .enumerate()
+            .filter_map(|(idx, item)| {
+                matches!(item, ResponseItem::Message { role, .. } if role == "user").then_some(idx)
+            })
+            .collect();
+        let Some(&first_user_idx) = user_positions.first() else {
+            return;
+        };
+
+        let n_from_end = usize::try_from(num_turns).unwrap_or(usize::MAX);
+        let cut_idx = if n_from_end >= user_positions.len() {
+            first_user_idx
+        } else {
+            user_positions[user_positions.len() - n_from_end]
+        };
+        items.truncate(cut_idx);
     }
 
     fn user_turn_count(items: &[ResponseItem]) -> usize {
@@ -5181,6 +5260,67 @@ mod tests {
         assert!(update_items.contains(&expected_item));
     }
 
+    #[test]
+    fn reconstruct_turn_context_history_handles_compaction() {
+        let collaboration_mode = CollaborationMode {
+            mode: ModeKind::Plan,
+            settings: Settings {
+                model: "gpt-test".to_string(),
+                reasoning_effort: None,
+                developer_instructions: None,
+            },
+        };
+        let turn_context = TurnContextItem {
+            cwd: PathBuf::from("/tmp"),
+            approval_policy: AskForApproval::Never,
+            sandbox_policy: SandboxPolicy::ReadOnly,
+            model: collaboration_mode.settings.model.clone(),
+            personality: None,
+            collaboration_mode: Some(collaboration_mode.clone()),
+            effort: None,
+            summary: ReasoningSummaryConfig::Auto,
+            user_instructions: None,
+            developer_instructions: None,
+            final_output_json_schema: None,
+            truncation_policy: None,
+        };
+        let user = ResponseItem::Message {
+            id: None,
+            role: "user".to_string(),
+            content: vec![ContentItem::InputText {
+                text: "first user".to_string(),
+            }],
+            end_turn: None,
+        };
+        let assistant = ResponseItem::Message {
+            id: None,
+            role: "assistant".to_string(),
+            content: vec![ContentItem::OutputText {
+                text: "assistant reply".to_string(),
+            }],
+            end_turn: None,
+        };
+        let compacted = RolloutItem::Compacted(CompactedItem {
+            message: format!("{}\nsummary", compact::SUMMARY_PREFIX),
+            replacement_history: None,
+        });
+
+        let rollout_items = vec![
+            RolloutItem::ResponseItem(user),
+            RolloutItem::TurnContext(turn_context),
+            RolloutItem::ResponseItem(assistant),
+            compacted,
+        ];
+        let history = Session::reconstruct_turn_context_history_from_rollout(&rollout_items);
+        let modes: Vec<Option<CollaborationMode>> = history
+            .iter()
+            .map(|item| item.as_ref().and_then(|ctx| ctx.collaboration_mode.clone()))
+            .collect();
+
+        assert_eq!(history.len(), 2);
+        assert_eq!(modes, vec![Some(collaboration_mode), None]);
+    }
+
     #[tokio::test]
     async fn thread_rollback_ignores_stale_turn_context() {
         let (sess, tc, rx) = make_session_and_context_with_rx().await;