There are lots of hoops and traps dealing with money now days because of 9/11 and Enron. My dental insurance company sent my Dentist a check for services I'd already paid for, so he just signed the check over to me. Couldn't do anything with it except start a fire. Reason? No check, regardless of the amount, written to a company can be deposited in a personal account without a legal representative of that company appearing in person and authorizing the transfer. New banking rule thanks to Enron.
As far as Fidelity, my employer used them for 401K accounts and I had accounts with them from previous jobs. When I retired I had no problems moving my money around. It might have a lot to do with the agent assigned to your account as to how easy things work.
