diff --git a/internal/cutoverorchestrator/generalprobe_test.go b/internal/cutoverorchestrator/generalprobe_test.go
index 32976513..6fbac6c4 100644
--- a/internal/cutoverorchestrator/generalprobe_test.go
+++ b/internal/cutoverorchestrator/generalprobe_test.go
@@ -124,7 +124,7 @@ func (d *Dryrun) injectShiftedRetentionDate(ctx context.Context) (Outcome, error
 		}
 		tag, err := pool.Exec(ctx, `
 			UPDATE retention_objects SET retain_until = retain_until + interval '48 hours'
-			WHERE id = (SELECT id FROM retention_objects WHERE retain_until IS NOT NULL ORDER BY id LIMIT 1)
+			WHERE id = (SELECT id FROM retention_objects WHERE retain_until > now() ORDER BY id LIMIT 1)
 		`)
 		if err != nil {
 			return Outcome{}, err