I hate driving in the mountains.... I'm scared hahah

if there is a yard donkey where you are get him to raise it
otherwise have fun cranking

 

Can you drop the air suspension on your tractor?
I'll do that and if I can get a little run at it I can usually get under most of the low trailers, as long as the back of my 5th wheel will slip under the plate on the trailer.
A lot of our loads are so heavy cranking the gear isn't a very good option.

 

Well that's no fun, sounds like someone is dropping the trailer too low or has a lower truck.
I'm lucky in that my tractor has drop/tag axels so when that happens I drop them and then air the suspension up again to take the load off the landing gear so I can crank it down a bit and then drop the air and raise the tags again to get under the trailer with the fifth wheel.
Maybe if you don't have tags you could try just airing up the tractor suspension to raise the trailer a little with the frame so you can crank the gear down a bit and then drop the air again to slide under.

 

I always do a tug test even if I looked to see the jaws were locked around the pin.

 

Well if you looked and did a tug and still dropped the trailer I would demand the tuck get to the shop, no way I'd drive it and worry about dropping a trailer in traffic.