So we'll keep using the pill box, and I'll enlist his participation in the weekly filling of it. And I believe I'll get him involved in the pharmacy refill aspect of this, too. He can at least watch me while I go through the steps. Then, perhaps in another few years he'll be able to take more control of this.
That's pretty much what we did with difficult child 1 and now with difficult child 3. We'd supervise the kids filling their containers, and with difficult child 1 I went with him to get other prescriptions filled (his dex is filled by mail order) and to also talk him through processing his doctors' bills (we have a direct phone line booth at the pharmacy, to the national health care provider - pick up the reciever and push the button, then follow the operator's instructions). Every little bit of info helps, every little experience and practice helps. It not only helps them in knowing what to do (and adapting it for other similar bits of paperwork) but they also get to increasingly appreciate what we do for them, without it usually being noticed.
And if you do this - then you know you are doing the best you can. After that, it's a roulette wheel plus guessing game, and we have to live with whatever falls.
Marg