I was able to transfer points to my brother's account but when we tried to transfer the points back due to a change of plans, the transaction wouldn't process. It was odd since these attempts were deducting points from our annual cap. I reached out to Lauren quite recently and she's trying to find out what happened. When I first reported the issue to Hilton, the Fraud Department was the first department to respond back and all they really had to say was that the account was clear and to try again. However, the transfers still didn't go through.
Hopefully, Hilton can get this resolved ASAP.