That's not going to work, extend_order_lease will be executed before do_sub_with_timeout gets called, so there'll be no chance for it to interrupt.

OP: How much code is in do_sub_with_timeout? Since the subroutine/method call is making it less readable, maybe there's no benefit in putting it in a subroutine? Maybe what you really want is a sub like handle_timeout which gets called if the timeout is exceeded.