After briefly reading the comments I decided to chime in a little bit.

First, 30 years on the inside...crazy. I don't think it is possible to put that in perspective. Cellphones were uncommon, the internet was still using "prodigy" and the likes, pagers were the "in thing". Forget trying to use the internet...these people have issues with the "number of decisions" in the grocery store (it is one of those areas where people quite literally freeze up, if you don't know feel free to look up the commissary options this person has had for 30 years).
Nothing looks the same, not neighborhoods, cars, clothing, people... You have been staring at guards for the last 30 years and an PA announcement has told you when/where to move and when to eat. Every day has been on repeat...

Now...30 years has passed and they let you out. What do you do...nothing but choices and a nearly constant flood of situations and experiences which you don't fully understand. Every task is something new to learn. And if you ask for help you are likely going to need to explain why you don't understand this stuff which may cause those people who were willing to help to second guess themselves and/or judge you.
You have nothing...assume your family/friends have mostly moved on (this happens even when you are not in prison often) and your only hope to have enough to get back on your feet is to fill out the mountains of forms required to get a portion of what you really need to live. Now imagine your only way to get those forms is to use the internet...it is very fortunate this person had a case worker who was willing to spend the time to help...many don't.

There is a non-zero amount of recidivism which is intentional. People get out and then decide the world moved on without them. They were better off not having choices or options they did not understand. Often, the hoops of parole are too much and they prefer to "top out" their time so they are not required to do things like keep a job which has paystubs (often you get paid way more under the table, as well as having bosses who don't undervalue your pay due to your criminal past), or find proper housing (halfway houses are required often for parole if you do not have someone who will vouch for you in a written letter). Not to mention that staying sober is hard at times, decide to get drunk on the wrong night or share a joint with someone and you are likely to face repercussions from your Parole officer.

It is a difficult situation. I have nothing but the utmost respect for the case manager. She very likely kept this person from either reoffending or worse killing themselves.

The programs on the inside are often not the best (depends on the state, program, and facility...some are private). If you think there is any way you can or would like to help in this situation maybe get in touch with some of the halfway houses or probation offices in your area. Your tech skills and abilities to navigate paperwork are much more valuable than you might understand. From there...you could look into possibly helping inside the prisons too (there may be other restrictions). Maybe even just look into mailing some books to the library there (last I checked they had to be shipped in by the vendor/bookstore). That book on Python may very well be the thing that changes their life...and possibly society.