diff --git a/.gitea/workflows/deploy.yml b/.gitea/workflows/deploy.yml
index c8606b6..915b006 100644
--- a/.gitea/workflows/deploy.yml
+++ b/.gitea/workflows/deploy.yml
@@ -1174,8 +1174,11 @@ jobs:
             if printf '%s' "${message}" | grep -q 'rancher-webhook'; then
               echo "Kustomization ${name} is blocked by Rancher webhook admission; waiting for webhook endpoints and retrying"
               wait_for_rancher_webhook_if_present
-              kubectl -n flux-system annotate "kustomization/${name}" reconcile.fluxcd.io/requestedAt="$(date +%s)" --overwrite >/dev/null
-              kubectl -n flux-system wait --for=condition=Ready "kustomization/${name}" --timeout="${timeout}"
+            fi
+
+            echo "Forcing retry for Kustomization ${name} after failed readiness wait"
+            kubectl -n flux-system annotate "kustomization/${name}" reconcile.fluxcd.io/requestedAt="$(date +%s)" --overwrite >/dev/null
+            if kubectl -n flux-system wait --for=condition=Ready "kustomization/${name}" --timeout="${timeout}"; then
               return 0
             fi