diff --git a/packages/cli/src/i18n/locales/ca.js b/packages/cli/src/i18n/locales/ca.js
index 2ac1b5414..75ac273d6 100644
--- a/packages/cli/src/i18n/locales/ca.js
+++ b/packages/cli/src/i18n/locales/ca.js
@@ -150,6 +150,8 @@ export default {
     'Codi restaurat, però la conversa no s’ha pogut retrocedir (cap client actiu).',
   'Conversation rewound. Edit your prompt and press Enter to continue.':
     'Conversa retrocedida. Edita la teva indicació i prem Retorn per continuar.',
+  'Rewinding does not affect files edited manually or via shell commands.':
+    'El retrocés no afecta els fitxers editats manualment o mitjançant comandes de shell.',
   'Failed to restore {{count}} file(s): {{files}}':
     'Error en restaurar {{count}} fitxer(s): {{files}}',
   'Cannot restore files: this turn was created before file checkpointing was enabled.':
diff --git a/packages/cli/src/i18n/locales/de.js b/packages/cli/src/i18n/locales/de.js
index 581061c16..a6079d20e 100644
--- a/packages/cli/src/i18n/locales/de.js
+++ b/packages/cli/src/i18n/locales/de.js
@@ -129,6 +129,8 @@ export default {
     'Code wiederhergestellt, aber Konversation konnte nicht zurückgespult werden (kein aktiver Client).',
   'Conversation rewound. Edit your prompt and press Enter to continue.':
     'Konversation zurückgespult. Bearbeite deinen Prompt und drücke Enter, um fortzufahren.',
+  'Rewinding does not affect files edited manually or via shell commands.':
+    'Das Zurückspulen wirkt sich nicht auf Dateien aus, die manuell oder per Shell-Befehl geändert wurden.',
   'Failed to restore {{count}} file(s): {{files}}':
     '{{count}} Datei(en) konnten nicht wiederhergestellt werden: {{files}}',
   'Cannot restore files: this turn was created before file checkpointing was enabled.':
diff --git a/packages/cli/src/i18n/locales/en.js b/packages/cli/src/i18n/locales/en.js
index df21b8209..ab19d1f1b 100644
--- a/packages/cli/src/i18n/locales/en.js
+++ b/packages/cli/src/i18n/locales/en.js
@@ -150,6 +150,8 @@ export default {
     'Code restored, but conversation could not be rewound (no active client).',
   'Conversation rewound. Edit your prompt and press Enter to continue.':
     'Conversation rewound. Edit your prompt and press Enter to continue.',
+  'Rewinding does not affect files edited manually or via shell commands.':
+    'Rewinding does not affect files edited manually or via shell commands.',
   'Failed to restore {{count}} file(s): {{files}}':
     'Failed to restore {{count}} file(s): {{files}}',
   'Cannot restore files: this turn was created before file checkpointing was enabled.':
diff --git a/packages/cli/src/i18n/locales/fr.js b/packages/cli/src/i18n/locales/fr.js
index 0424ed7ce..0292418a8 100644
--- a/packages/cli/src/i18n/locales/fr.js
+++ b/packages/cli/src/i18n/locales/fr.js
@@ -150,6 +150,8 @@ export default {
     'Code restauré, mais la conversation n’a pas pu être ramenée en arrière (aucun client actif).',
   'Conversation rewound. Edit your prompt and press Enter to continue.':
     'Conversation ramenée en arrière. Modifiez votre invite et appuyez sur Entrée pour continuer.',
+  'Rewinding does not affect files edited manually or via shell commands.':
+    'Le retour en arrière n’affecte pas les fichiers édités manuellement ou via des commandes shell.',
   'Failed to restore {{count}} file(s): {{files}}':
     'Échec de la restauration de {{count}} fichier(s) : {{files}}',
   'Cannot restore files: this turn was created before file checkpointing was enabled.':
diff --git a/packages/cli/src/i18n/locales/ja.js b/packages/cli/src/i18n/locales/ja.js
index fa89cb3f2..52acec9bd 100644
--- a/packages/cli/src/i18n/locales/ja.js
+++ b/packages/cli/src/i18n/locales/ja.js
@@ -110,6 +110,8 @@ export default {
     'コードは復元されましたが、会話は巻き戻せませんでした（モデルクライアントがアクティブではありません）。',
   'Conversation rewound. Edit your prompt and press Enter to continue.':
     '会話を巻き戻しました。プロンプトを編集して Enter キーで続行してください。',
+  'Rewinding does not affect files edited manually or via shell commands.':
+    '巻き戻しは、手動で編集されたファイルや shell コマンドで変更されたファイルには影響しません。',
   'Failed to restore {{count}} file(s): {{files}}':
     '{{count}} 個のファイルの復元に失敗しました：{{files}}',
   'Cannot restore files: this turn was created before file checkpointing was enabled.':
diff --git a/packages/cli/src/i18n/locales/pt.js b/packages/cli/src/i18n/locales/pt.js
index c3459c918..411ade85d 100644
--- a/packages/cli/src/i18n/locales/pt.js
+++ b/packages/cli/src/i18n/locales/pt.js
@@ -144,6 +144,8 @@ export default {
     'Código restaurado, mas a conversa não pôde ser retrocedida (sem cliente ativo).',
   'Conversation rewound. Edit your prompt and press Enter to continue.':
     'Conversa retrocedida. Edite seu prompt e pressione Enter para continuar.',
+  'Rewinding does not affect files edited manually or via shell commands.':
+    'O retrocesso não afeta arquivos editados manualmente ou por meio de comandos shell.',
   'Failed to restore {{count}} file(s): {{files}}':
     'Falha ao restaurar {{count}} arquivo(s): {{files}}',
   'Cannot restore files: this turn was created before file checkpointing was enabled.':
diff --git a/packages/cli/src/i18n/locales/ru.js b/packages/cli/src/i18n/locales/ru.js
index f683e0455..43c63430e 100644
--- a/packages/cli/src/i18n/locales/ru.js
+++ b/packages/cli/src/i18n/locales/ru.js
@@ -153,6 +153,8 @@ export default {
     'Код восстановлен, но разговор не удалось откатить (нет активного клиента).',
   'Conversation rewound. Edit your prompt and press Enter to continue.':
     'Разговор откатили. Отредактируйте подсказку и нажмите Enter, чтобы продолжить.',
+  'Rewinding does not affect files edited manually or via shell commands.':
+    'Откат не затрагивает файлы, отредактированные вручную или с помощью shell-команд.',
   'Failed to restore {{count}} file(s): {{files}}':
     'Не удалось восстановить {{count}} файл(ов): {{files}}',
   'Cannot restore files: this turn was created before file checkpointing was enabled.':
diff --git a/packages/cli/src/i18n/locales/zh-TW.js b/packages/cli/src/i18n/locales/zh-TW.js
index f919ae2ef..a95131d4b 100644
--- a/packages/cli/src/i18n/locales/zh-TW.js
+++ b/packages/cli/src/i18n/locales/zh-TW.js
@@ -133,6 +133,8 @@ export default {
     '程式碼已恢復，但對話無法回退（模型客戶端未啟用）。',
   'Conversation rewound. Edit your prompt and press Enter to continue.':
     '對話已回退。修改提示後按 Enter 繼續。',
+  'Rewinding does not affect files edited manually or via shell commands.':
+    '回退不會影響手動編輯或透過 shell 命令修改的檔案。',
   'Failed to restore {{count}} file(s): {{files}}':
     '恢復 {{count}} 個檔案失敗：{{files}}',
   'Cannot restore files: this turn was created before file checkpointing was enabled.':
diff --git a/packages/cli/src/i18n/locales/zh.js b/packages/cli/src/i18n/locales/zh.js
index d08e9695a..98b6c8c5a 100644
--- a/packages/cli/src/i18n/locales/zh.js
+++ b/packages/cli/src/i18n/locales/zh.js
@@ -144,6 +144,8 @@ export default {
     '代码已恢复，但对话无法回退（模型客户端未激活）。',
   'Conversation rewound. Edit your prompt and press Enter to continue.':
     '对话已回退。修改你的提示后按回车继续。',
+  'Rewinding does not affect files edited manually or via shell commands.':
+    '回退不会影响手工编辑或通过 shell 命令修改的文件。',
   'Failed to restore {{count}} file(s): {{files}}':
     '恢复 {{count}} 个文件失败：{{files}}',
   'Cannot restore files: this turn was created before file checkpointing was enabled.':
diff --git a/packages/cli/src/ui/components/RewindSelector.tsx b/packages/cli/src/ui/components/RewindSelector.tsx
index d22a3a196..0bd829d88 100644
--- a/packages/cli/src/ui/components/RewindSelector.tsx
+++ b/packages/cli/src/ui/components/RewindSelector.tsx
@@ -420,6 +420,17 @@ export function RewindSelector({
                     </Box>
                   );
                 })}
+                {restoreOptions.some(
+                  (o) => o.key === 'code' || o.key === 'both',
+                ) && (
+                  <Box marginTop={1}>
+                    <Text color={theme.text.secondary} dimColor>
+                      {t(
+                        'Rewinding does not affect files edited manually or via shell commands.',
+                      )}
+                    </Text>
+                  </Box>
+                )}
               </Box>
             )}
           </Box>
diff --git a/packages/core/src/services/fileHistoryService.test.ts b/packages/core/src/services/fileHistoryService.test.ts
index 667373228..6ae47d07b 100644
--- a/packages/core/src/services/fileHistoryService.test.ts
+++ b/packages/core/src/services/fileHistoryService.test.ts
@@ -158,6 +158,40 @@ describe('FileHistoryService', () => {
         snapshots[0].trackedFileBackups[p1Key].backupFileName,
       );
     });
+
+    // When a per-file backup attempt throws inside makeSnapshot, the new
+    // snapshot must NOT silently inherit the previous snapshot's backup
+    // and present it as the captured state of this turn — that would
+    // make a later rewind restore older content while reporting success.
+    // Instead the snapshot records a `failed: true` marker so rewind
+    // surfaces the file via filesFailed and getDiffStats omits it.
+    it('marks per-file backup failures and does not silently inherit', async () => {
+      const file = join(projectDir, 'a.txt');
+      await writeFile(file, 'p1-content');
+
+      await service.makeSnapshot('p1');
+      await service.trackEdit(file);
+
+      // Modify the file and break the backup target (replace storageDir
+      // with a regular file → ENOTDIR inside `safeCopyFile`'s recursive
+      // mkdir). The next makeSnapshot's per-file backup attempt throws.
+      await writeFile(file, 'p2-content');
+      await rm(storageDir, { recursive: true, force: true });
+      await writeFile(storageDir, '');
+
+      await service.makeSnapshot('p2');
+
+      const p2Backups = service.getSnapshots()[1].trackedFileBackups;
+      const p2Backup = p2Backups['a.txt'];
+      expect(p2Backup).toBeDefined();
+      expect(p2Backup.failed).toBe(true);
+
+      // Rewind to p2 must report the file as failed, not silently
+      // restore p1-content as if it were the captured state of p2.
+      const result = await service.rewind('p2');
+      expect(result.filesChanged).toEqual([]);
+      expect(result.filesFailed).toContain(file);
+    });
   });
 
   describe('rewind', () => {
diff --git a/packages/core/src/services/fileHistoryService.ts b/packages/core/src/services/fileHistoryService.ts
index 89901ca27..afb80b016 100644
--- a/packages/core/src/services/fileHistoryService.ts
+++ b/packages/core/src/services/fileHistoryService.ts
@@ -27,6 +27,13 @@ export interface FileHistoryBackup {
   backupFileName: BackupFileName;
   version: number;
   backupTime: Date;
+  // Set when makeSnapshot's per-file backup attempt threw. Distinguishes
+  // "we have a confirmed backup of this file at this snapshot" from
+  // "we tried to capture this file at this snapshot but failed (so the
+  // attached backup, if any, is older than this turn)". Rewind / diff
+  // surface failed paths via filesFailed instead of silently restoring
+  // stale content as if it were current.
+  failed?: boolean;
 }
 
 export interface FileHistorySnapshot {
@@ -265,6 +272,17 @@ async function computeDiffStatsForFile(
   return { filesChanged, insertions, deletions };
 }
 
+/**
+ * Tracks file edits made through the assistant's `edit` and `write_file`
+ * tools so `/rewind` can roll the workspace back to the state at a chosen
+ * turn boundary.
+ *
+ * Scope (intentional, mirrors upstream claude-code): only files touched
+ * via `edit` and `write_file` are tracked. Changes made via
+ * `run_shell_command` (`sed -i`, `cp`, `mv`, `rm`, `npm` scripts, `git`
+ * apply, etc.) and any out-of-tool manual edits are NOT captured, and
+ * `/rewind` cannot restore them.
+ */
 export class FileHistoryService {
   private state: FileHistoryState = {
     snapshots: [],
@@ -395,6 +413,18 @@ export class FileHistoryService {
             debugLogger.error(
               `FileHistory: Failed to backup file ${trackingPath}: ${error}`,
             );
+            // Record the failure rather than letting the inheritance loop
+            // silently copy the previous snapshot's backup — that would
+            // make a rewind to this snapshot restore the file to its
+            // pre-failure content as if it were the captured state of
+            // this turn.
+            const previous = mostRecent?.trackedFileBackups[trackingPath];
+            trackedFileBackups[trackingPath] = {
+              backupFileName: previous?.backupFileName ?? null,
+              version: this.getMaxVersion(trackingPath) + 1,
+              backupTime: new Date(),
+              failed: true,
+            };
           }
         }),
       );
@@ -469,6 +499,12 @@ export class FileHistoryService {
           const filePath = this.maybeExpandFilePath(trackingPath);
           const targetBackup = targetSnapshot.trackedFileBackups[trackingPath];
 
+          // The backup attempt failed at the target snapshot; we cannot
+          // produce a meaningful diff against a content we never captured,
+          // so omit this file from the preview rather than show a diff
+          // versus an older inherited backup.
+          if (targetBackup?.failed) return null;
+
           const backupFileName: BackupFileName | undefined = targetBackup
             ? targetBackup.backupFileName
             : this.getBackupFileNameFirstVersion(trackingPath);
@@ -527,6 +563,14 @@ export class FileHistoryService {
         const filePath = this.maybeExpandFilePath(trackingPath);
         const targetBackup = targetSnapshot.trackedFileBackups[trackingPath];
 
+        // makeSnapshot couldn't capture this file at the target turn.
+        // Surface it as failed instead of restoring the carried-over
+        // (older) backup as if it were the captured state.
+        if (targetBackup?.failed) {
+          filesFailed.push(filePath);
+          continue;
+        }
+
         const backupFileName: BackupFileName | undefined = targetBackup
           ? targetBackup.backupFileName
           : this.getBackupFileNameFirstVersion(trackingPath);