Weird, I've just checked and the achievement seems to be unlocking fine overall (44% unlock according to true achievements, which is normal).
The objectives are here, and they come in waves so it CAN be easy to miss one:
- Hire more workmen to speed up demolition (Simply press cn_right, go to Hire Staff and pick Workman - I had 30 at the end)
- Handle the food need of your prisoners
- Handle the recreational needs of your prisoners
- Handle the environmental need of your prisoners
- Have 3 prisoners pass the Alcoholics Group Therapy program
- Have 3 prisoners pass the Drug Addiction program
- Build a Laundry Room
- Hire 10 Janitors
- Handle the clothing needs of your prisoners
The other thing I normally suggest, if you're sure you're hitting them all, is restarting the game and seeing if it pops then.