• Agent on laptop, Server on Kube - Fail

So I'm 100% sure there is something wrong with our ClearML Server deployment on Kube

Yeah that feels like a network config issue...

Is there a verbose setting in the agent that could help us diagnose,

yes running with debug turned on on.
since you managed to reproduce on your latop you can try to run the agent with --debug to test, specifically:

clearml-agent --debug daemon ....

if you are running it in venv mode (which I think the setup) you can also just specify the Task ID and test that (no daemon just execution)

clearml-agent --debug execute --id <task_id_here>