If you take a supply job with a destination at a military airport, you have a problem, that you cant plan a flight to go there. When you try to plan a flight, you cant select that military airport as a destination, because the “Choose” button is grayed out.
As a workaround you can plan a flight at any other airport and simply land at the needed military airport and finish tracking of your flight there.
Since you dont get a penalty for landing at a military airport without a permission, it looks like the supply job correctly issues you a permision, but “Plan a flight” page doesnt see it or doesnt check for it.
I dont have screenshots, but it was the supply job finished with the 69484 flight