diff --git a/gateway/slash_commands.py b/gateway/slash_commands.py
index 6c32606974..001d6b7469 100644
--- a/gateway/slash_commands.py
+++ b/gateway/slash_commands.py
@@ -3487,6 +3487,14 @@ class GatewaySlashCommandsMixin:
                     "gateway.rollback.kept_oversize",
                     files=shown + more,
                 )
+            failed = result.get("failed_deletes") or []
+            if failed:
+                shown = ", ".join(failed[:5])
+                more = f" (+{len(failed) - 5})" if len(failed) > 5 else ""
+                msg += "\n" + t(
+                    "gateway.rollback.failed_deletes",
+                    files=shown + more,
+                )
             return msg
         return t("gateway.rollback.restore_failed", error=result["error"])
 
diff --git a/hermes_cli/cli_commands_mixin.py b/hermes_cli/cli_commands_mixin.py
index d399f2fa1e..d16050a495 100644
--- a/hermes_cli/cli_commands_mixin.py
+++ b/hermes_cli/cli_commands_mixin.py
@@ -170,6 +170,11 @@ class CLICommandsMixin:
                 shown = ", ".join(oversize[:5])
                 more = f" (+{len(oversize) - 5} more)" if len(oversize) > 5 else ""
                 print(f"  ↷ Kept (too large for checkpoints, no stored copy to revert to): {shown}{more}")
+            failed = result.get("failed_deletes") or []
+            if failed:
+                shown = ", ".join(failed[:5])
+                more = f" (+{len(failed) - 5} more)" if len(failed) > 5 else ""
+                print(f"  ⚠️ Could not remove (left in place): {shown}{more}")
             print("  A pre-rollback snapshot was saved automatically.")
 
             # Also undo the last conversation turn so the agent's context
diff --git a/locales/af.yaml b/locales/af.yaml
index b1606af7bd..4a5aa89bd6 100644
--- a/locales/af.yaml
+++ b/locales/af.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ Herstel na kontrolepunt {hash}: {reason}\n'n Voor-terugrol-momentopname is outomaties gestoor."
     kept_user_edits:       "↷ Jou handwysigings is behou: {files}\nGebruik /rollback <N> --all om dié ook te herstel."
     kept_oversize:         "↷ Behou (te groot vir kontrolepunte, geen gestoorde kopie om na terug te keer nie): {files}"
+    failed_deletes:        "⚠️ Kon nie verwyder nie (in plek gelaat): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/ar.yaml b/locales/ar.yaml
index 8230c2c2c9..933b10f361 100644
--- a/locales/ar.yaml
+++ b/locales/ar.yaml
@@ -301,6 +301,7 @@ gateway:
     restored:              "✅ استُعيد إلى نقطة التحقّق {hash}: {reason}\nحُفظت لقطة ما قبل التراجع تلقائيًا."
     kept_user_edits:       "↷ احتُفظ بتعديلاتك اليدوية: {files}\nاستخدم ‎/rollback <N> --all لاستعادتها أيضًا."
     kept_oversize:         "↷ احتُفظ به (أكبر من أن يُحفظ في نقاط التفتيش، لا توجد نسخة مخزنة للرجوع إليها): {files}"
+    failed_deletes:        "⚠️ تعذّرت الإزالة (تُرك الملف في مكانه): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/de.yaml b/locales/de.yaml
index c7006020f8..8a18ff65cf 100644
--- a/locales/de.yaml
+++ b/locales/de.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ Auf Checkpoint {hash} wiederhergestellt: {reason}\nEin Pre-Rollback-Snapshot wurde automatisch gespeichert."
     kept_user_edits:       "↷ Deine manuellen Änderungen wurden behalten: {files}\nNutze /rollback <N> --all, um auch diese wiederherzustellen."
     kept_oversize:         "↷ Behalten (zu groß für Checkpoints, keine gespeicherte Kopie zum Zurücksetzen): {files}"
+    failed_deletes:        "⚠️ Konnte nicht entfernt werden (an Ort und Stelle belassen): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/en.yaml b/locales/en.yaml
index dbce02e0c4..34b0904cf0 100644
--- a/locales/en.yaml
+++ b/locales/en.yaml
@@ -293,6 +293,7 @@ gateway:
     restored:              "✅ Restored to checkpoint {hash}: {reason}\nA pre-rollback snapshot was saved automatically."
     kept_user_edits:       "↷ Kept your hand-edits: {files}\nUse /rollback <N> --all to restore those too."
     kept_oversize:         "↷ Kept (too large for checkpoints, no stored copy to revert to): {files}"
+    failed_deletes:        "⚠️ Could not remove (left in place): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/es.yaml b/locales/es.yaml
index 65fa1aab15..a51c05ef82 100644
--- a/locales/es.yaml
+++ b/locales/es.yaml
@@ -278,6 +278,7 @@ gateway:
     restored:              "✅ Restaurado al checkpoint {hash}: {reason}\nSe guardó automáticamente un snapshot previo al rollback."
     kept_user_edits:       "↷ Se conservaron tus ediciones manuales: {files}\nUsa /rollback <N> --all para restaurarlas también."
     kept_oversize:         "↷ Conservado (demasiado grande para los checkpoints, no hay copia guardada a la que revertir): {files}"
+    failed_deletes:        "⚠️ No se pudo eliminar (se dejó en su lugar): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/fr.yaml b/locales/fr.yaml
index 481494a8d3..df65467285 100644
--- a/locales/fr.yaml
+++ b/locales/fr.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ Restauré au point de contrôle {hash} : {reason}\nUn instantané pré-rollback a été enregistré automatiquement."
     kept_user_edits:       "↷ Vos modifications manuelles ont été conservées : {files}\nUtilisez /rollback <N> --all pour les restaurer aussi."
     kept_oversize:         "↷ Conservé (trop volumineux pour les checkpoints, aucune copie enregistrée vers laquelle revenir) : {files}"
+    failed_deletes:        "⚠️ Suppression impossible (laissé en place) : {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/ga.yaml b/locales/ga.yaml
index 4658541457..ff061d4471 100644
--- a/locales/ga.yaml
+++ b/locales/ga.yaml
@@ -285,6 +285,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ Aischurtha go seicphointe {hash}: {reason}\nSábháladh roghchóip réamh-rollback go huathoibríoch."
     kept_user_edits:       "↷ Coinníodh do chuid athruithe láimhe: {files}\nÚsáid /rollback <N> --all chun iad sin a aischur freisin."
     kept_oversize:         "↷ Coinnithe (ró-mhór do sheicphointí, níl aon chóip stóráilte le filleadh uirthi): {files}"
+    failed_deletes:        "⚠️ Níorbh fhéidir a bhaint (fágtha ina áit): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/hu.yaml b/locales/hu.yaml
index 334a6f9838..d85807ae21 100644
--- a/locales/hu.yaml
+++ b/locales/hu.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ Visszaállítva a(z) {hash} ellenőrzőpontra: {reason}\nA visszaállítás előtti pillanatkép automatikusan elmentve."
     kept_user_edits:       "↷ A kézi szerkesztéseid megmaradtak: {files}\nHasználd a /rollback <N> --all parancsot, hogy azokat is visszaállítsd."
     kept_oversize:         "↷ Megtartva (túl nagy az ellenőrzőpontokhoz, nincs tárolt másolat, amire vissza lehetne állni): {files}"
+    failed_deletes:        "⚠️ Nem sikerült eltávolítani (a helyén maradt): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/it.yaml b/locales/it.yaml
index 4124945df3..8a7c55b861 100644
--- a/locales/it.yaml
+++ b/locales/it.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ Ripristinato al checkpoint {hash}: {reason}\nUno snapshot pre-rollback è stato salvato automaticamente."
     kept_user_edits:       "↷ Le tue modifiche manuali sono state conservate: {files}\nUsa /rollback <N> --all per ripristinare anche quelle."
     kept_oversize:         "↷ Conservato (troppo grande per i checkpoint, nessuna copia salvata a cui tornare): {files}"
+    failed_deletes:        "⚠️ Impossibile rimuovere (lasciato al suo posto): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/ja.yaml b/locales/ja.yaml
index c96bf559a6..7f1bed5918 100644
--- a/locales/ja.yaml
+++ b/locales/ja.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ チェックポイント {hash} に復元しました: {reason}\nロールバック前のスナップショットが自動的に保存されました。"
     kept_user_edits:       "↷ 手動編集は保持されました: {files}\nそれらも復元するには /rollback <N> --all を使用してください。"
     kept_oversize:         "↷ 保持しました（チェックポイントには大きすぎるため、戻せる保存コピーがありません）: {files}"
+    failed_deletes:        "⚠️ 削除できませんでした（そのまま残っています）: {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/ko.yaml b/locales/ko.yaml
index 07990df2e4..b240547aaf 100644
--- a/locales/ko.yaml
+++ b/locales/ko.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ 체크포인트 {hash}(으)로 복원됨: {reason}\n롤백 전 스냅샷이 자동으로 저장되었습니다."
     kept_user_edits:       "↷ 직접 수정한 내용은 유지되었습니다: {files}\n해당 파일도 복원하려면 /rollback <N> --all 을 사용하세요."
     kept_oversize:         "↷ 유지됨 (체크포인트에 저장하기엔 너무 커서 되돌릴 저장본이 없습니다): {files}"
+    failed_deletes:        "⚠️ 제거할 수 없었습니다 (그대로 남아 있음): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/pt.yaml b/locales/pt.yaml
index c40b0c0389..7a8a131c5d 100644
--- a/locales/pt.yaml
+++ b/locales/pt.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ Restaurado para o checkpoint {hash}: {reason}\nFoi guardado automaticamente um snapshot anterior ao rollback."
     kept_user_edits:       "↷ As suas edições manuais foram mantidas: {files}\nUse /rollback <N> --all para restaurar essas também."
     kept_oversize:         "↷ Mantido (grande demais para os checkpoints, sem cópia guardada para reverter): {files}"
+    failed_deletes:        "⚠️ Não foi possível remover (mantido no lugar): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/ru.yaml b/locales/ru.yaml
index be08f04435..a4220d3d28 100644
--- a/locales/ru.yaml
+++ b/locales/ru.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ Восстановлено до контрольной точки {hash}: {reason}\nСнимок перед откатом сохранён автоматически."
     kept_user_edits:       "↷ Ваши ручные правки сохранены: {files}\nИспользуйте /rollback <N> --all, чтобы восстановить и их."
     kept_oversize:         "↷ Сохранено (слишком большой для контрольных точек, нет сохранённой копии для отката): {files}"
+    failed_deletes:        "⚠️ Не удалось удалить (файл оставлен на месте): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/tr.yaml b/locales/tr.yaml
index 791c364c16..c0ffa802a3 100644
--- a/locales/tr.yaml
+++ b/locales/tr.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ {hash} kontrol noktasına geri yüklendi: {reason}\nGeri alma öncesi anlık görüntü otomatik olarak kaydedildi."
     kept_user_edits:       "↷ Elle yaptığınız düzenlemeler korundu: {files}\nOnları da geri yüklemek için /rollback <N> --all kullanın."
     kept_oversize:         "↷ Korundu (denetim noktaları için çok büyük, geri dönülecek kayıtlı kopya yok): {files}"
+    failed_deletes:        "⚠️ Kaldırılamadı (yerinde bırakıldı): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/uk.yaml b/locales/uk.yaml
index 123b70f079..43ccae3911 100644
--- a/locales/uk.yaml
+++ b/locales/uk.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ Відновлено до контрольної точки {hash}: {reason}\nЗнімок перед відкатом збережено автоматично."
     kept_user_edits:       "↷ Ваші ручні правки збережено: {files}\nВикористайте /rollback <N> --all, щоб відновити і їх."
     kept_oversize:         "↷ Збережено (завеликий для контрольних точок, немає збереженої копії для відкату): {files}"
+    failed_deletes:        "⚠️ Не вдалося видалити (залишено на місці): {files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/zh-hant.yaml b/locales/zh-hant.yaml
index f61216e45d..1b26f787fd 100644
--- a/locales/zh-hant.yaml
+++ b/locales/zh-hant.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ 已還原至檢查點 {hash}：{reason}\n已自動儲存回復前的快照。"
     kept_user_edits:       "↷ 已保留您的手動編輯：{files}\n若也要還原這些檔案，請使用 /rollback <N> --all。"
     kept_oversize:         "↷ 已保留（檔案過大無法納入檢查點，沒有可還原的儲存副本）：{files}"
+    failed_deletes:        "⚠️ 無法移除（保留原檔）：{files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/locales/zh.yaml b/locales/zh.yaml
index 686cb1ea55..d7bed9149d 100644
--- a/locales/zh.yaml
+++ b/locales/zh.yaml
@@ -281,6 +281,7 @@ Future messages in this room will use that transcript until `/reset` or another
     restored:              "✅ 已恢复到检查点 {hash}：{reason}\n已自动保存回滚前的快照。"
     kept_user_edits:       "↷ 已保留您的手动编辑：{files}\n如需一并恢复这些文件，请使用 /rollback <N> --all。"
     kept_oversize:         "↷ 已保留（文件过大无法纳入检查点，没有可恢复的存储副本）：{files}"
+    failed_deletes:        "⚠️ 无法移除（保留原文件）：{files}"
     restore_failed:        "❌ {error}"
 
   diff:
diff --git a/tests/tools/test_checkpoint_manager.py b/tests/tools/test_checkpoint_manager.py
index 62499fe71c..67cdaac9f6 100644
--- a/tests/tools/test_checkpoint_manager.py
+++ b/tests/tools/test_checkpoint_manager.py
@@ -527,6 +527,7 @@ class TestSafeRestore:
         assert not scratch.exists()
         assert "scratch.txt" in result["restored_files"]
         assert result["skipped_oversize"] == []
+        assert "failed_deletes" not in result
 
     def test_safe_restore_does_not_report_a_failed_delete_as_restored(
         self, mgr, work_dir, monkeypatch,
@@ -554,6 +555,7 @@ class TestSafeRestore:
         assert result["success"] is True
         assert stubborn.exists()
         assert "stubborn.txt" not in result["restored_files"]
+        assert result["failed_deletes"] == ["stubborn.txt"]
 
     def test_unsafe_restore_overwrites_everything(self, mgr, work_dir):
         base = self._checkpoint(mgr, work_dir)
diff --git a/tools/checkpoint_manager.py b/tools/checkpoint_manager.py
index 7c821fbeb2..1061874b41 100644
--- a/tools/checkpoint_manager.py
+++ b/tools/checkpoint_manager.py
@@ -1098,7 +1098,10 @@ class CheckpointManager:
         With ``safe=True`` (full-directory restores only), files the user
         hand-edited after Hermes' last write — per the agent-write ledger —
         are left untouched, and only Hermes-authored changes are reverted.
-        The result gains ``skipped_user_edits`` listing the preserved paths.
+        The result gains ``skipped_user_edits`` listing the preserved paths,
+        ``skipped_oversize`` listing paths kept because the size cap excluded
+        them from every checkpoint, and — only when a delete failed —
+        ``failed_deletes`` listing paths that could not be removed.
         """
         hash_err = _validate_commit_hash(commit_hash)
         if hash_err:
@@ -1146,6 +1149,7 @@ class CheckpointManager:
                         "directory": abs_dir,
                         "restored_files": [],
                         "skipped_user_edits": skipped_user_edits,
+                        "skipped_oversize": [],
                     }
 
         # Take a pre-rollback snapshot so you can undo the undo.