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I might be having a similar issue (except I'm not seeing any error related to tls certificate).
I can open a separate issue if this is unrelated. If you need any testing or additional logs, please let me know.I also just recreated the TalosUpgrade resource, and it proceeds normally. link to my config
2026-01-07T15:23:46.164393387Z 2026-01-07T15:23:46Z INFO Starting reconciliation {"controller": "talosupgrade", "controllerGroup": "tuppr.home-operations.com", "controllerKind": "TalosUpgrade", "TalosUpgrade": {"name":"talos"}, "namespace": "", "name": "talos", "reconcileID": "5ba2deca-3989-40a3-9882-8da270105d00", "talosupgrade": "talos"} 2026-01-07T15:23:46.164606370Z 2026-01-07T15:23:46Z DEBUG Starting upgrade processing {"controller": "talosupgrade", "controllerGroup": "tuppr.home-operations.com", "controllerKind": "TalosUpgrade", "TalosUpgrade": {"name":"talos"}, "namespace": "", "name": "talos", "reconcileID": "5ba2deca-3989-40a3-9882-8da270105d00", "talosupgrade": "talos", "generation": 3} 2026-01-07T15:23:46.164653818Z 2026-01-07T15:23:46Z DEBUG Upgrade already completed or failed {"controller": "talosupgrade", "controllerGroup": "tuppr.home-operations.com", "controllerKind": "TalosUpgrade", "TalosUpgrade": {"name":"talos"}, "namespace": "", "name": "talos", "reconcileID": "5ba2deca-3989-40a3-9882-8da270105d00", "talosupgrade": "talos", "generation": 3, "phase": "Completed"} 2026-01-07T15:25:58.318964941Z 2026-01-07T15:25:58Z INFO Starting KubernetesUpgrade reconciliation {"controller": "kubernetesupgrade", "controllerGroup": "tuppr.home-operations.com", "controllerKind": "KubernetesUpgrade", "KubernetesUpgrade": {"name":"kubernetes"}, "namespace": "", "name": "kubernetes", "reconcileID": "d4cdae99-3a78-4e57-b930-f6ba4deae872", "kubernetesupgrade": "kubernetes"} 2026-01-07T15:25:58.319395443Z 2026-01-07T15:25:58Z DEBUG Starting Kubernetes upgrade processing {"controller": "kubernetesupgrade", "controllerGroup": "tuppr.home-operations.com", "controllerKind": "KubernetesUpgrade", "KubernetesUpgrade": {"name":"kubernetes"}, "namespace": "", "name": "kubernetes", "reconcileID": "d4cdae99-3a78-4e57-b930-f6ba4deae872", "kubernetesupgrade": "kubernetes", "generation": 4} 2026-01-07T15:25:58.319444687Z 2026-01-07T15:25:58Z DEBUG Kubernetes upgrade already completed or failed {"controller": "kubernetesupgrade", "controllerGroup": "tuppr.home-operations.com", "controllerKind": "KubernetesUpgrade", "KubernetesUpgrade": {"name":"kubernetes"}, "namespace": "", "name": "kubernetes", "reconcileID": "d4cdae99-3a78-4e57-b930-f6ba4deae872", "kubernetesupgrade": "kubernetes", "generation": 4, "phase": "Completed"}
Originally posted by @tscibilia in #65
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