Serhiy Storchaka added the comment:

> Would there be a way to automatically switch the flag as necessary?
> (i.e. when writing more than 2GB, I guess)

Yes, there is a special flag for this in zipfile. It is named allowZip64.

The only reason to use allowZip64=False is when you expect to unzip a zipfile 
with a tool which doesn't support zip64 (PKUNZIP.EXE for DOS?) and you want to 
keep yourself from unintentional zipping a file larger than 2 GiB.

Perhaps sometime we should to change the default value for allowZip64 from 
False to True.

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nosy: +serhiy.storchaka

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Python tracker <rep...@bugs.python.org>
<http://bugs.python.org/issue17189>
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