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I've read that with YUM it automatically will download and install whatever dependencies it has when you tell it to install/upgrade a package.
I have a RHEL server that only has up2date on it, which I've read doesn't automatically do dependencies. So before I tell it to update a certain package, are there certain things I need to check for first before I issue the command? I've read the following link but am still confused http://www.cyberciti.biz/faq/howto-use-up2date-command/
Up2date does resolve dependencies. It will let you know that it is resolving them too (if it does have to). It gives you a graphical interface so it's real easy. If you're coming into the box remotely, do an 'ssh -Y root@<yourbox>' and you'll pop the X interface back to the box you're coming from. Since you are unfamiliar with it, this would be easiest.
I always do dry runs before actually applying updates. Check the man pages for yum and up2date for the options to check for whatever packages will be marked for updates and you can then make sure nothing that is updated will potentially break your system.
I always have a spare machine not part of a production environment I use to test before applying to machines that matter.