<human>: Can you give me the gist of the text in a nutshell?

Reddit - can I get your advice?  During college (I just graduated), I volunteer tutored/taught weekly for 3 years a medium security youth prison. I grew very attached (not romantically) to several of my students, and in particular, one that I have tutored consistently the last 3 years. He is still in prison until next January, but is taking a deal with the US Army that wipes his record. He is very bright and motivated and I am so proud of his accomplishments. With the deal, his dream to become a lawyer is actually a possibility.

As a volunteer, we were given a very strict set of guidelines of what not to do (touch prisoners, give/take anything, exchange information etc.) which includes contact after we leave the program. But I'm tempted to write to him and see how he's doing  and continue to teach via letter...?

Is this is a very bad idea? I am worried it'll be misconstrued. I vacillate between thinking it's not such a big deal (just letters, would be really helpful to him, I have a little bit of mother-teresa syndrome where I probably think I have a bigger impact than I actually do) and where I think it's a really poor decision (...he is still in prison. I am putting myself at some level of risk).
<bot>: I used to teach at a prison during college, want to write to a former student who has potential to really change his life, don't know if it's too risky/naive of me.