diff --git a/apps/server/src/production/orchestration_effects.rs b/apps/server/src/production/orchestration_effects.rs
index 5190fa76b4..22ed75128d 100644
--- a/apps/server/src/production/orchestration_effects.rs
+++ b/apps/server/src/production/orchestration_effects.rs
@@ -2809,7 +2809,10 @@ async fn plan_shared_restore(
                 cancellation,
             )
             .await?;
-            if !changes.turns.is_empty() {
+            // Turns in the window are not the only outside work: a deleted chat can
+            // write after this thread's last checkpoint, past the event window, and
+            // those paths are what `git clean` would delete.
+            if changes.outside_changes() {
                 acknowledge_sibling_changes(thread_id, turn_count, &changes, token)?;
                 return Ok((
                     fallback_to_head,
@@ -3090,8 +3093,9 @@ pub(crate) async fn preview_checkpoint_revert(
         ),
         _ => None,
     };
-    // A deleted chat's changes count only when it changed files since the target.
-    let changes = changes.filter(|changes| shared || !changes.turns.is_empty());
+    // A deleted chat counts when it has turns in the window or files changed since
+    // this thread's last checkpoint. Either one is work a restore would discard.
+    let changes = changes.filter(|changes| shared || changes.outside_changes());
     let conversation_rewind = match probe {
         Some(probe) => probe
             .conversation_rewind(thread_id)
diff --git a/apps/server/src/production/shared_checkout_restore_tests.rs b/apps/server/src/production/shared_checkout_restore_tests.rs
index 596d02c66a..dd59518e4e 100644
--- a/apps/server/src/production/shared_checkout_restore_tests.rs
+++ b/apps/server/src/production/shared_checkout_restore_tests.rs
@@ -1541,6 +1541,41 @@ async fn a_sibling_conversation_only_rewind_keeps_its_changes_in_the_warning() {
     }
 }
 
+#[tokio::test]
+async fn a_deleted_chat_file_change_since_the_last_turn_needs_the_token() {
+    let fixture = Fixture::new().await;
+    // B's only session event is before A's turn 1, so the event window has no sibling turn.
+    // The file was written after A's last checkpoint: a restore would delete it.
+    fixture.engine.dispatch(command(json!({"type":"thread.delete", "commandId":"delete-b", "threadId":"b", "createdAt":T_LAST}))).await.unwrap();
+    std::fs::write(fixture.repo.join("notes.txt"), "kept by a deleted chat\n").unwrap();
+    let preview = fixture.preview("a", 1).await;
+    assert_eq!(preview["siblingChanges"]["paths"], json!(["notes.txt"]));
+    assert_eq!(preview["siblingChanges"]["turns"], json!([]));
+    let token = preview["siblingChangesToken"]
+        .as_str()
+        .expect("a deleted chat's later files still need acknowledging")
+        .to_owned();
+    let failure = fixture.revert("a", 1, "full", None).await.unwrap_err();
+    assert!(
+        detail(&failure).contains("changed since turn 1"),
+        "{failure}"
+    );
+    assert_eq!(failure["siblingChangesToken"], json!(token));
+    assert_eq!(
+        std::fs::read_to_string(fixture.repo.join("notes.txt")).unwrap(),
+        "kept by a deleted chat\n",
+        "the unacknowledged restore must not delete the file"
+    );
+    assert_eq!(fixture.tracked(), "two\n");
+    fixture.revert("a", 1, "full", Some(&token)).await.unwrap();
+    assert!(
+        !fixture.repo.join("notes.txt").exists(),
+        "the acknowledged restore still cleans the file"
+    );
+    assert_eq!(fixture.tracked(), "one\n");
+    fixture.shutdown().await;
+}
+
 #[tokio::test]
 async fn a_terminal_edit_since_the_last_turn_is_listed() {
     let fixture = Fixture::new().await;
diff --git a/docs/architecture/rpc-and-orchestration.md b/docs/architecture/rpc-and-orchestration.md
index 0c2883641f..d8e1924b64 100644
--- a/docs/architecture/rpc-and-orchestration.md
+++ b/docs/architecture/rpc-and-orchestration.md
@@ -3970,9 +3970,12 @@ conversation-rewind support and `siblingChangesToken`: the SHA-256 of the
 target commit, the current tree id and the sorted event ids. A full revert on a
 shared checkout proceeds only when its token matches the one recomputed under
 the gate. A request without a token (an older client) proceeds only when no
-outside change exists. Otherwise the refusal carries the new token in its
-activity payload. The preview is advisory, runs Git, and is in
-`is_long_running`. It needs `orchestration:operate`, as a revert does: its
+outside change exists. A checkout whose other chats are all deleted still
+counts: their turns in that window, and any files changed since this thread's
+last checkpoint, are outside changes. When the token is missing or stale, the
+refusal carries the new token in its activity payload. The preview is advisory,
+runs Git, and is in `is_long_running`. It needs `orchestration:operate`, as a
+revert does: its
 `git add` into a temporary index runs the repository's clean filters, which can
 run commands on the host.