Licensing Not Updating On Phone User

I've assigned a US/CA Unlimited Calling Plan / Pro Features · Unlimited Domestic license to a user, but the user is still getting a message sorry you cannot place this call, your calling plan does not support calling to this destination. They are placing an external call via a desk phone (Yealink T54W)

I've already tried to remove the license and readd it, I've also tried deleting the user and recreating it. Still getting the same results. It's been around 12 hours since I setup the new user and am still getting the same results, so I dont believe it's because the system hasn't synced or anything. I've also tried resyncing the phone.