diff --git a/internal/agent/recording_cleanup_proof.go b/internal/agent/recording_cleanup_proof.go
index f63b620..dd249ec 100644
--- a/internal/agent/recording_cleanup_proof.go
+++ b/internal/agent/recording_cleanup_proof.go
@@ -93,6 +93,10 @@ func (r *RecordingRecovery) preserveCleanupProof(entry RecordingRecoveryEntry) (
 	if err := privateCleanupDirectory(dir); err != nil {
 		return "", err
 	}
+	// A prior attempt may have created the namespace but failed its sync.
+	if err := syncDirectory(r.Root); err != nil {
+		return "", err
+	}
 	before, err := r.readCleanupProof(path)
 	if err == nil {
 		original, marshalErr := json.Marshal(entry)
@@ -103,6 +107,11 @@ func (r *RecordingRecovery) preserveCleanupProof(entry RecordingRecoveryEntry) (
 		if !bytes.Equal(original, persisted) {
 			return "", errors.New("recording cleanup proof conflicts with current recording")
 		}
+		// Also retry a previously failed rename-directory sync before unlinking
+		// originals; seeing the receipt in this process is not durability proof.
+		if err := syncDirectory(dir); err != nil {
+			return "", err
+		}
 		return path, nil
 	}
 	if !errors.Is(err, os.ErrNotExist) {