When I install a new port, does it upgrade any already installed ports
if the new port depends on them.  And to upgrade any security fixes,
just running cvsup on the ports tree, then running portupgrade?

Also, is there any way to automate this, I have a freebsd mail server
setup for a company that I may not get to visit very often.  Then again,
it may not be the wisest to upgrade software with no one to monitor it.

Is there any way to select just major security and avoid upgrading ports
that just add features?

And does the freebsd kernel also get upgraded.  Would I have to
reinstall it or would the port do it automatically?

I sense much NT in you.
NT leads to Bluescreen.
Bluescreen leads to downtime.
Downtime leads to suffering.
NT is the path to the darkside.
Powerful Unix is.

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