I have seen images on the 2 quart fill of C8 DCT where suggested is using either the fill or drain plugs to inject 2 quarts of DCT fluid into the DCT
Really makes no difference if the fill one is used as seen is right by the DCT filter and doing this using air pressure can cause that pressure
through the DCT filter and I doubt it can handle pressure like that
Imagine a mistake and using 125 PSI for this type of fill process
Also have seen that only the whole left side of C8 be jacked up at a high angle
The car was not designed for that and could cause a weight shift/load and break something
I am first hand in that being doing as having driven 1,500 plus to race at ORR out of Texas
I had the local Chevy dealer then replace the engine oil
I then went to practice, was running over 160 MPH, went to slow down and C4 ZR-1 about flipped over and only decades of racing was I able to get car stopped
Got out of car to find Mobile I engine oil covering everything from front all the way to back end, including both left brakes soaked in oil and the tires

Turns out the damn tech at dealer did the same, instead of proper jacking of car they only jacked up the left side so car was titled up high causing shift/.stress
which broke a weld of external oil cooler
I still say it is a one time job to add a fill hose to top of DCT so hose then is placed where it can be reached easy in future fills,
car on the ground and no need of any compressed air being used.
One image example on how close the DCT filter is to where the OP suggests the fill be done: