RedKhan16 added a comment.

  Here is all the log entries file for this command
  F33997715: upload-bot.log <https://phabricator.wikimedia.org/F33997715>
  Just in case you are wondering - I'm running pywikibot from Windows Subsystem 
for Linux.
  
  As for the restrictions made by the site. That's what I initially thought and 
here is their answer:
  
  > From what I am reading from here: 
https://www.mediawiki.org/wiki/API:Upload#Upload_warnings ignore_warnings must 
be set to reupload. I do see, however, that pybot is giving an error in 
reference to ignore_warnings. As far as I am aware, nothing has changed in 
reference to our API that would differ it from core MediaWiki 1.33. If you have 
the latest version of pybot and are ignoring warnings, I would suggest filing a 
bug with pybot here: 
https://phabricator.wikimedia.org/maniphest/task/create/?projects=PHID-PROJ-orw42whe2lepxc7gghdq
 (Or hop on their IRC server for consult/triage/bug reporting: 
https://webchat.freenode.net/?channels=pywikibot)

TASK DETAIL
  https://phabricator.wikimedia.org/T271871

EMAIL PREFERENCES
  https://phabricator.wikimedia.org/settings/panel/emailpreferences/

To: RedKhan16
Cc: Multichill, Xqt, Aklapper, pywikibot-bugs-list, RedKhan16, JohnsonLee01, 
SHEKH, Dijkstra, Khutuck, Zkhalido, Viztor, Wenyi, Tbscho, MayS, Mdupont, 
JJMC89, Dvorapa, Altostratus, Avicennasis, mys_721tx, jayvdb, Masti, 
Alchimista, Rxy
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