This, it's also unclear who OP owes the money to, it sounds like the school directly. Not sure what the expectation was about the military covering thing proactively.

Nor do we really understand why this is a priority all a sudden. If the time constraint is that the old school needs paid before they will release a transcript so they can start at the new school this will need to be figured out first. This isn't an uncommon problem.

OP Needs to explain the situation in detail because we don't know the situation or the poster enough to infer the details.