* a UI change to check the box this information is on
* UI change to view whether the box is already checked or not
* a data model change to store the information
* business logic change that modifies some critical code that calculates when someone should be released
* security/access control change to decide who is allowed to check this box
* auditing logic to keep logs of this stuff
* possibly new UI/management code to add/remove members to this group of people who can check the box
* together with adding some procedures for tracking who completes what, documentation, training and auditing.
* Testing the whole thing.
Probably for piles of who knows what where the original author is long gone and the test code is no longer functional.
Just to keep things in perspective.
2. What I described is not the actual fix, it is the temporary stopgap. The prison department isn't going to pay someone to click checkboxes all the time for tens of thousands of inmates each year. They will want this info to be set automatically -- e.g. an integration from whatever software system(s) are used to track completion of the coursework to this system, so you are not hiring another employee to sit and click all the time nor do you need to create reporting procedures to get that info into the hands of the person who is clicking. The appropriate design then requires automation, which will require security controls, and it's a pain. It could easily be more than a year of work, again depending on how many systems they need to integrate against, what types of sign off/controls are required, how much paperwork is required, etc.
For example, maybe the coursework has no software tracking, in which case they need to throw up a portal and have the people running the course fill out who did what, and then throw up another portal to have someone else review that.
Lots of stuff ends up being passed around by ftp or csv uploads. I've seen horror stories. So it really depends on how they plan to do this integration -- the manual button clicking was just an example of a least effort system that relied on a lot of manual labor, but perhaps this is not in their budget either.