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Again, not all prisons are the same.

There are federal and state prisons, and county jails. There are maxiumum security prisons and medical centers and juvenile detention centers and more. Each prison is different. Glad the prison your friend was at let you give money directly through the prison website, they don't all do that.

Same with book policies and shit. Each prison has different rules about the kinds of books they will accept and the companies they will accept them with. Whenever possible, people should of course buy books from local anarchist publishers like LBC and send books. And I never buy books from amazon directly (for a variety of reasons) though I have used amazon to buy used books from 3rd party sellers. But actually, not all prisons accept used books. Or they change their mind on that.

When it comes to prison support, really, there isn't a lot of consistent information to give other than: Find a friend. ask them what they need. Research the regulations at the prison they are at. And then follow the regulations. That's pretty much all it takes to do some solid shit for your friends who are locked up.