The difficulty with social engineering training is that one of the core reasons social engineering works is that no one believes it will happen to them. Very few people believe that anyone is capable of talking them out of their millions (or thousands or whatever) but it does get done. They think 419 scammers and the like, while really social engineers look just like normal people with normal jobs and normal lives; they just occasionally talk their way into a little bit extra. This lack of belief from the majority of people makes social engineering training actually easier to do in a live environment than in a test environment, as a role player will know they are to be social engineered and will hold onto whatever secret information they have with tooth and claw. There are, however, some methods of simulating a live environment.

It's important to note that it is incredibly unethical to social engineer private information out of people for further...