diff --git a/src/pobsync_backend/retention.py b/src/pobsync_backend/retention.py
index 5136224..5c52908 100644
--- a/src/pobsync_backend/retention.py
+++ b/src/pobsync_backend/retention.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
 import shutil
+import stat
 from datetime import datetime, timezone
 from pathlib import Path
 from typing import Any
@@ -89,17 +90,17 @@ def run_sql_retention_apply(
             if snap_kind not in {"scheduled", "manual"}:
                 raise ConfigError(f"Refusing to delete unsupported snapshot kind: {snap_kind!r}")
 
-            path = Path(snap_path)
+            path = _snapshot_delete_path(path=Path(snap_path), dirname=dirname)
             if not path.exists():
                 actions.append(f"skip missing {snap_kind}/{dirname}")
                 continue
             if not path.is_dir():
-                raise ConfigError(f"Refusing to delete non-directory path: {snap_path}")
+                raise ConfigError(f"Refusing to delete non-directory path: {path}")
 
-            shutil.rmtree(path)
+            _remove_snapshot_tree(path)
             SnapshotRecord.objects.filter(host__host=host, kind=snap_kind, dirname=dirname).delete()
             actions.append(f"deleted {snap_kind} {dirname}")
-            deleted.append({"dirname": dirname, "kind": snap_kind, "path": snap_path})
+            deleted.append({"dirname": dirname, "kind": snap_kind, "path": str(path)})
 
         return {
             "ok": True,
@@ -180,3 +181,22 @@ def _snapshot_to_delete_item(snapshot: Snapshot) -> dict[str, Any]:
         "dt": snapshot.dt.isoformat(),
         "status": snapshot.status,
     }
+
+
+def _snapshot_delete_path(*, path: Path, dirname: str) -> Path:
+    if path.name == "data" and path.parent.name == dirname:
+        return path.parent
+    return path
+
+
+def _remove_snapshot_tree(path: Path) -> None:
+    _make_directories_user_writable(path)
+    shutil.rmtree(path)
+
+
+def _make_directories_user_writable(path: Path) -> None:
+    for directory in [path, *[child for child in path.rglob("*") if child.is_dir() and not child.is_symlink()]]:
+        mode = directory.stat().st_mode
+        if mode & stat.S_IWUSR:
+            continue
+        directory.chmod(mode | stat.S_IWUSR)
diff --git a/src/pobsync_backend/tests/test_sql_retention.py b/src/pobsync_backend/tests/test_sql_retention.py
index 846c38d..32302ab 100644
--- a/src/pobsync_backend/tests/test_sql_retention.py
+++ b/src/pobsync_backend/tests/test_sql_retention.py
@@ -1,6 +1,7 @@
 from __future__ import annotations
 
 import json
+import stat
 from datetime import datetime, timezone
 from io import StringIO
 from pathlib import Path
@@ -85,6 +86,42 @@ class SqlRetentionTests(TestCase):
             self.assertFalse(SnapshotRecord.objects.filter(pk=old.pk).exists())
             self.assertEqual(result["deleted"], [{"dirname": old.dirname, "kind": "scheduled", "path": str(old_dir)}])
 
+    def test_apply_deletes_snapshot_with_readonly_data_directory(self) -> None:
+        with TemporaryDirectory() as tmp:
+            prefix = Path(tmp) / "home"
+            host = HostConfig.objects.create(
+                host="web-01",
+                address="web-01.example.test",
+                retention_daily=0,
+                retention_weekly=0,
+                retention_monthly=0,
+                retention_yearly=0,
+            )
+            old_dir = Path(tmp) / "backups" / host.host / "scheduled" / "20260518-021500Z__OLD"
+            old_data = old_dir / "data"
+            old_data.mkdir(parents=True)
+            old_data.joinpath("etc").mkdir()
+            old_data.joinpath("etc", "config").write_text("preserved permissions\n")
+            old_data.chmod(stat.S_IREAD | stat.S_IEXEC | stat.S_IRGRP | stat.S_IXGRP | stat.S_IROTH | stat.S_IXOTH)
+            new_dir = Path(tmp) / "backups" / host.host / "scheduled" / "20260519-021500Z__NEW"
+            new_dir.mkdir(parents=True)
+            old = self._snapshot(host, old_dir.name, path=str(old_data))
+            self._snapshot(host, new_dir.name, path=str(new_dir))
+
+            result = run_sql_retention_apply(
+                prefix=prefix,
+                host=host.host,
+                kind="scheduled",
+                protect_bases=False,
+                yes=True,
+                max_delete=1,
+                acquire_lock=False,
+            )
+
+            self.assertFalse(old_dir.exists())
+            self.assertFalse(SnapshotRecord.objects.filter(pk=old.pk).exists())
+            self.assertEqual(result["deleted"], [{"dirname": old.dirname, "kind": "scheduled", "path": str(old_dir)}])
+
     def test_apply_respects_max_delete(self) -> None:
         host = HostConfig.objects.create(
             host="web-01",