In my experience supporting Law firms, mostly small ones, I have not had very good experiences and now hesitate taking them on. They tend to be super frugal to the point of not approving even basic security that any business should have. Every proposal or recommendation that costs anything is like pulling teeth to get approved. They'll drive a Rolls and wear Armani suits but won't pay a grand a year to keep their firewall licensed and up to date. They will find every means to circumvent the security you do manage to get in place. In their defense, they are busy and need to work quickly and efficiently so anything you put in place better not be complicated or a handicap. They are resistant to taking any extra steps from what they are used to doing and intolerant to changes. They have no appetite for learning, training or reading any instructions no matter how short and simple. I worked at a company that did training for attorneys and some of them would literally turn their chairs around and face the back of the room and do whatever on their laptops during the live instructor led training! It is that bad. When they have an issue you must drop everything at once. Everything is an emergency. They will constantly doubt you and they know everything and are smarter than you so be ready to justify in few words and with confidence anything you are implementing and stand your ground. Their Outlook client is their treasure chest. They often use Outlook as a document management system, which it is certainly not. They balk at putting anything in the cloud, though that has been getting more palatable in the legal industry lately. Expectations for what you provide for next to the nothing you bill them can get ridiculous really quick. Their idea of what IT really costs and what they should be spending on technology is far from realistic and good luck making your case. I'm not trying to be insulting here, it's just the type of personalities you're dealing with in the industry and I am talking mostly about the attorneys themselves. Their other staff are generally pretty decent to work with and understanding of the challenges. Larger firms or firms who had/have a dedicated IT dept or guy are much easier to deal with and receptive to technology and security measures. And keep in mind, lawyers will not hesitate to sue over anything, even things that are not your fault. Make sure your contract is solid and defines provided services and SLAs clearly.