choco
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Support upgrading Cygwin packages
Cygwin setup supports --upgrade-also (see https://cygwin.com/faq/faq.html#faq.setup.cli) which allows Cygwin to perform an unattended upgrade of all installed packages.
choco upgrade -s=cygwin all
Related to #1355
Thanks for the issue and the contribution! We'll take a look at this in more depth hopefully in the next few weeks.
If this moves forward, consider also Python's PIP. (Will create as issue in the future if/when relevant.)
I'd like to reconsider this feature; the PR is still viable.