Patching

There are very few Operating Systems that have an adequate patching process for applications. The only two I recommend to someone who is too busy to track all of their installed applications is FreeBSD and Debian GNU/Linux. Apparently you can do this with RedHat and its offspring, but I've heard about a lot of issues with "dependancy hell."

It should be noted that "dependancy hell" is usually because the SysAdmin has installed packages from different distributions. For example, installing SuSE packages on a RedHat system is asking for trouble. Packages built for a specific RedHat version almost always work, as do packages rebuilt from .src.rpm files. (RedHat and other RPM-based systems are quite a bit nicer once you learn to rollo your own RPM .spec files)

Debian

Using Debian GNU/Linux it's as simple as

apt-get update
apt-get dist-upgrade

and all of your installed applications will now be up to date. You can modify where you get your updates from the /etc/apt/sources.list file.

FreeBSD

I've created two shell scripts which I've named update, and upgrade. You will need portsnap, portaudit and portupgrade installed to use these:

 #!/bin/sh
 # update
 /usr/local/sbin/portsnap fetch && /usr/local/sbin/portsnap update && pkg_version  -v -l < #EOF
 
 
 #!/bin/sh
 # upgrade
 portaudit -F && portaudit
 portupgrade -a
 #EOF

Windows

Use internet explorer to go to Microsoft update. Let it scan your computer and install all of the high-priority/recommended updates. If you have an issue installing a patch, say for example KB913580, take a look for the log file in C:\Windows for patchname.log. i.e.

C:\WINDOWS\KB913580.log

open the file in notepad.exe, at the bottom of the file you will hopefully find a searchable error message or error code.

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Rumour has it that OpenBSD is building a portupgrade-ish tool, and I will surely switch to them at that point, based on their security history.