Okay let me see if I can think of something...
Basically crashing on the assertion here ?
https://github.com/ultralytics/yolov5/blob/d95978a562bec74eed1d42e370235937ab4e1d7a/train.py#L495
Could it be your are passing "Args/resume" True, but not specifying the checkpoint ?
https://github.com/ultralytics/yolov5/blob/d95978a562bec74eed1d42e370235937ab4e1d7a/train.py#L452
I think I know what's going on:
https://github.com/ultralytics/yolov5/blob/d95978a562bec74eed1d42e370235937ab4e1d7a/train.py#L452
does not specify a type: specifically it can take boolean or string pointing to a Path.
What's going on is that it gets "False" as string from the cloned Task, then the automagic does not cast it to boolean because the definition of the args is "nartgs="?"" and no type, so it leaves it as string, then the assertion fails because it checks if this is a string.
Does that make sense ?