Bench update issues due to gitpython

[trentmu]

@Ubfacility_Saas

Retrying (Retry(total=2, connect=None, read=None, redirect=None, status=None)) after connection broken by ‘SSLError(SSLError(“bad handshake: Error([(‘SSL routines’, ‘tls_process_server_certificate’, ‘certificate verify failed’)],)”,),)’: /simple/gitpython/

seems to be the source of your problem. This link resolved a similar problem (but module was num2words instead of pip/pillow). Maybe try reinstalling pip/pillow this way

No matching distribution found for num2words==0.5.4

go to frappe-bench directory, then bench setup env ./env/bin/pip2 install --force-reinstall num2words==0.5.4 bench switch-to-master bench update --requirements bench retry-upgrade

Otherwise, have a look at this link to a link

ConnectionError when trying to access web service using zeep in custom app

Maybe this link could be helpful.