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One of the funniest malware I ever encountered was a Message Box that popped up whenever my brother's PC would start up into windows and say "poker?" (in small case). I always found it incredibly funny, especially because of the small case.
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Some malware are based on impersonation, it counts on the user to mis-recognize the displayed screen and think it is generated by a legitimate application. Some malware, however, do this very badly, which creates funny results. (red labels are impossible in regular Windows MessageBoxes, so are links.)
The interesting question (design-wise) is:
how bad can they get before normal users figure it out?
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