This honestly makes me think that we're missing a trick if an option for this sort of circumstance can't be "send a military fuel tanker up to refuel them in air" as a last ditch emergency measure (which IMO you would've triggered in this exact scenario).

The argument in favor is simply that we need in air refueling for the military, but justifying all that expenditure is a lot easier if it's dual use technology.

Isn't midair refueling notoriously difficult to get right? The headlines would become "airliner crashes after crew couldn't thread the needle for 45 min"

It's a ridiculous proposition.