Any mention of teaching behind bars tends to elicit a degree of interest and even respect that is quite disproportionate to the task performed. In response to questions, here's an account of a typical evening of teaching inmates. Be warned, though, that this will be quite prosaic. Adrenaline-charged teaching happens in urban high schools. Teaching in prison is relatively uneventful.
There are, of course, a lot of security measures. Instructors sign in and show ID cards three times on their way to the classrooms, and on your first trip the clanging gates and metal detectors do make a bit of an impression. Soon all of this recedes into the background, however, and your mind focuses on the "teacher lounge" chatter as you wait in line after line. You discuss the evening's lesson, your plans for the weekend, the weather. The cs geeks wrap themselves in an incomprehensible exchange about some arcane programming issue and you laugh at them or ignore them (all the instructors are volunteers, and most are grad students at nearby colleges, and many are friends from the same research departments). The most exciting thing that ever happens is that some newbie gets caught for having absentmindedly brought in his or her cell phone and has to return to the car with it and go through each gate over again.
Once all security checkpoints are passed the Corrections Officer (CO) who supervises the building unlocks the classrooms. You pick up the box of materials for your class from the locker, take out the sign-in sheet, and start writing the agenda on the board. Students trickle in, and go about doing what they're supposed to do: they sign in, sharpen their pencils, take out their materials, and take notes or do practice problems or take quizzes. You lecture or tutor, as the case might be, and give students feedback on their work. The students ask questions and hand you answer as best you can. After about an hour there is a break, and the "close custody" students leave. You have about an hour after that for more teaching, but out of consideration for the students that must leave early you avoid covering new material.
When class is over you pack your materials back into the boxes, put the boxes into the locker, and troop to the first of three checkpoints to sign out. The discussions among the instructors on the way home are often similarly mundane: Why are fractions so hard for the students? What's a better way of explaining the Ruler Postulate? Is the pacing of the course appropriate? How can we improve communication among instructors who teach on different evenings? And do we want Mexican or Thai food for dinner?
You read all the way to the end? I told you it wouldn't be terribly exciting. You get on with teaching math and afterward you go home and sleep. Actually, I'm lying a bit: the instructor team, predominantly made up of Ph.D. students in Math or Science, is a pretty agreeable bunch to hang out with. I mean, if you're a public school teacher you've got to love a group of remarkably bright people whose strongest interests include Math or Science and equitable access to education. The dinner discussions after class can be really entertaining, and on one occasion we built a fire on the beach and toasted marshmallows under a starry sky before going home. So there's that. As far as level of pedagogical and interpersonal challenges go, however, it does not compare with high school teaching at all. In fact, the students' level of focus, interest in the material and general politeness make this teaching a pleasant and relaxed summer vacation activity.