For example, did you ever have an appointment reminder pop up on your screen when you're in the middle of typing something important? The reminder ''steals'' the keyboard, so suddenly you're typing your job application cover letter into your doctor's appointment reminder. Ghastly.
There should be a special place in hell for those folks who turned Skype into nag-ware. Can you imagine if your cell phone kept jumping out of your pocket and yelling "Isn't it time you called your friends?" (I shouldn't have said that. Now someone will make just such a phone.)
How about Facebook's continual revision of privacy policies, requiring you to modify your settings repeatedly to avoid having your personal information go out on WikiLeaks?
And of course Facebook also brings this perennial favorite:
Of course, Adobe Photoshop also gives us helpful messages like this one:
And let's not forget all Web sites that start blaring audio as soon as you land there. Mandatory sentencing. Likewise for sites that require you to download and open a PDF to find the information that should have been on a Web page in the first place!
As for punishment, I kind of lean towards the stocks, or some other form of public humiliation.
I'll add to this list as I think of more. Feel free to comment with your personal favorites.