If

Dataset.upload()

does not crash or return a success value that I can check and

Are you saying that with this error showing upload data does not crash? (edited)

Unfortunately that is correct. It continues as if nothing happened!

To replicate this in linux (even with max_workers=1 ):
https://averagelinuxuser.com/limit-bandwidth-linux/ to throttle your connection: sudo apt-get install wondershaper
Throttle your connection to 1mb/s with something like sudo wondershaper wlo1 1024 1024
(where wlo1 is my network connection)
Run the attached script: python dataset_fail.py

(to stop throttling: sudo wondershaper clear wlo1 )