Anarchie is one of my favourite Mac OS applications, partly because I had so much input into its design. It also contains some of the most subtle human interface design I've yet encountered. In fact one of the most difficult things we've found with its design is that many users can't find it's cool features and hence never appreciate the program.
One of the steps we took to address this was active assistance. Anarchie watches your actions and, if you consistently perform actions "the hard way" it reminds you that there is an easier way.
The two examples of this are:
One of the most important things about this active assistance is that its implementation is not annoying. If you want to ignore the assistance and think "Damnit, I'm used to typing 'anonymous', and I don't want the computer telling me what to do anyway!", then you can ignore the hints and Anarchie will slowly back off, eventually only reminding you once in a blue moon.