Holidays are coming, so here is a list of some of my favorite, can't live without 'em software utilities
Exam Diff Pro - best software I know for examining differences in files and directories. Incredibly easy to use, to customize and very reliable.
FinePrint - allows you to do all sorts of fancy printing, but I use it to print pages 2-up and cut my paper and toner usage in half.
Hypersnap DX - screen capture. Virtually every screen capture in all my books for the past 5 years have been done with this software. Saves to virtually any format.
Roboform - For IE (6 or 7). I don't know how anyone lives without this. Fill in your information and it fills forms for you (including, if you want, credit cards, etc.) Can be password protected. Remembers login and password info for sites you visit, can provide password generation. Many more features. Invaluable.
Trillian - Integrates AIM, Yahoo, MSN, and others and the interface and ease of use (and logging of chat records) is superior to the native interfaces.