The Emily Post Of Prison

A white collar criminal’s guide to behind-bars etiquette. There are rules for this sort of thing.

- Andrew Goldman

So you got caught. That porn star wasn’t about to pay herself to stay mum about her night with your boss, so you stepped up and took one for the team. Or perhaps your daughters were better at Instagram than calculus, so you spent half a million bucks pretending they were the best college athletic prospects since O.J. Simpson. Or maybe the SEC decided you were less of a “cryptoguru” and more of a charlatan.

From Lori Loughlin to Michael Cohen, nearly every day brings a notable figure face to face with a possible jail sentence—which, in turn, has given rise to a cottage industry: the prison consultancy. From companies like California’s White Collar Advice, which boasts a team of professionals with penal experience (as convicts or as employees of the Federal Bureau of Prisons) to individual entrepreneurs like Federal Prison Handbook author Christopher Zoukis, they have made it positively de rigueur for those more accustomed to sleeping between Pratesi than polyester to hire an insider who will lay out what to expect when expecting to be incarcerated. They charge thousands for their advice (and some six figures for help managing your affairs while you are inside), but we rounded up some of the top consultants—as well as some high-profile prisoners—to ask for their most crucial insights. Because, you know, you never know.

1 WHERE EXACTLY ARE YOU GOING?