With a proper tubeless tyre on a proper tubeless rim you need to really crack it off the rim bed. You can lose all the pressure in the tyre without the seal around the bead breaking. Also once it's sealed the first time it's much easier to inflate in future.
Big hole= use two of the plugs.
You don't have to get it to stick to the rim as you never unstuck it (as you would have done to get a tube in).