t seems there is some async behavior going on. After ending a run, this prompt just hangs for a long time:

2021-04-18 22:55:06,467 - clearml.Task - INFO - Waiting to finish uploads

And there's no sign of updates on the dashboard

Hmm that could point to an issue uploading the last images (which are larger than regular scalars) could you try flushing and waiting ?
i.e.
task.flush() sleep(45)