Moxie Marlinspike, public face of Open Whisper Systems, identifies with anarchism. They include political radicals in most of their images of the application. It's not promoting criminality, except insofar as opposing state repression is criminal. Opposing state repression is the raison d'etre of OWS. I can't speak for them, but I suspect the fact that they're using software to do it is a secondary consideration.

Could be a fun tip of the hat (so to speak) to the old saying: "When freedom is outlawed, only outlaws will be free."

OWS quite often use anarchist figures and quotes in their example images for blog posts, this is nothing new.