Okie girl, when Difficult Child was in jail the first two or three times, I sent books, wrote letters and cards, accepted phone call charges, visited and put money on his account for clothing and snacks and other things.
As he continued to go back to jail (final count was I lost count!!! It was 8 or 9 times before he got scared straight, as he calls it) I slowly stopped doing all of it, over time, except write him very short postcards.
when I found out that he was playing cards all day long and gambling the things I had been paying for (his canteen stuff), I stopped putting money on the account.
Like most things with him, I learned over time what I was willing to do and what was really going on. I know being in jail must be really hard. I hate that my precious son put himself there for even one minute.
But over time, I began to realize jail must simply not be that bad, because he kept going back there, over and over and over again. And I came to be relieved when he was in jail, because that meant he was "somewhere" in my mind, instead of sleeping outside on the street, which was very hard for me to live with. It was a relief when he was in jail.
I think you have gotten good advice here. I would call the jail and ask the questions that you have. I found that the people here in Tennessee were nice when I called and they answered my questions.
Hang in there. This too will pass. Your son is now somewhere with three hots and a cot, as they say. We're here for you.