diff --git a/termstory/backup.py b/termstory/backup.py
index 5f08a1d..779b62e 100644
--- a/termstory/backup.py
+++ b/termstory/backup.py
@@ -46,8 +46,9 @@ def backup_db() -> str:
             oldest = backups.pop(0)
             if os.path.exists(oldest):
                 os.remove(oldest)
-    except OSError as e:
-        logger.warning("Failed to rotate old backups: %s", e)
+    except OSError:
+        # Rotation failure should not crash the backup process, but it must be visible.
+        logger.exception("Failed to rotate old backups in %s", backup_dir)
 
     return backup_path
 
diff --git a/tests/test_backup.py b/tests/test_backup.py
index e67a11c..6bc18e9 100644
--- a/tests/test_backup.py
+++ b/tests/test_backup.py
@@ -1,3 +1,4 @@
+import logging
 import os
 import pytest
 from termstory.backup import backup_db, restore_db
@@ -84,3 +85,46 @@ def now(cls):
     import glob
     remaining = glob.glob(os.path.join(backup_dir, "termstory_backup_*.db"))
     assert len(remaining) == 10
+
+
+def test_backup_survives_rotation_failure(tmp_path, monkeypatch, caplog):
+    db_file = tmp_path / "test_rotation_failure.db"
+    db_path = str(db_file)
+    monkeypatch.setenv("DB_PATH", db_path)
+    monkeypatch.setattr("termstory.config.get_db_path", lambda: db_path)
+    monkeypatch.setattr("termstory.backup.get_db_path", lambda: db_path)
+
+    db = Database(db_path)
+    db.init_db()
+
+    class MockDatetime:
+        counter = 0
+        @classmethod
+        def now(cls):
+            cls.counter += 1
+            from datetime import datetime as dt
+            return dt(2026, 6, 18, 19, 0, cls.counter)
+
+    monkeypatch.setattr("termstory.backup.datetime", MockDatetime)
+
+    # Fill past the rotation threshold so cleanup runs and hits the failing os.remove.
+    for _ in range(11):
+        backup_db()
+
+    def boom(_path):
+        raise PermissionError("cannot delete backup")
+
+    monkeypatch.setattr("termstory.backup.os.remove", boom)
+
+    # Rotation now fails, but the backup itself must still succeed and return a path.
+    with caplog.at_level(logging.ERROR, logger="termstory.backup"):
+        backup_path = backup_db()
+
+    assert os.path.isfile(backup_path)
+
+    # The rotation failure must be logged, not silently swallowed. A regression
+    # back to `except OSError: pass` would drop this record and fail here.
+    assert any(
+        "Failed to rotate old backups" in record.message
+        for record in caplog.records
+    )