Hi, as much as I hate to say this, if you give an addict money for drugs on the out and they request money for drugs whilst in prison (indirectly of course) then yes you are enabling. My partner used to ring me saying he needed phone credit, extra bits from the canteen and blah blah blah.
I stopped sending him money but he found other ways and when he was released from prison he was back on the drugs with a few hours. I know some people might disagree with me but I stopped visiting and removed all contact with him when inevitably he ended up in prison again because what is the point? I am all for supporting a person if they are determined to detox and battle their addiction but I'm no push-over and the lies he came out with were corkers! I remember getting a phone call from some drug dealer in prison demanding money and I basically told him to **** off and that I was having nothing to do with my partner. We split up after that and he's now seeing another drug addict so hey, at least they've both something in common and get romantically high with each other. Good luck to them. It's not a life I want and I gave him chance after chance. I did my bit and I cannot control the way he chooses to live his life.