Is there a way to centrally administer cygwin, i.e. run remote updates on multiple boxes from a central 'admin machine'?
basic goal: keep sshd up to date on all instances
stretch goal: keep everything up to date and in sync.
thanks
Cygwin's setup.exe
supports command line arguments. You maybe be able to manage packages with that. Just be aware that if 'cygwin1.dll' is updated in the process it may break running Cygwin sessions so they will need to be restarted.
The Superuser stack exchange site has a question that covers this in more detail.