Question for exclusively pumping mamas

My baby just turned 5 months and has become really fussy with nursing. If he doesn’t get a letdown within 10 seconds he’ll start screaming and crying which is exhausting, especially at night. I can deal with it during the day because I can usually calm him down and get the letdown to happen, but I’m considering pumping at night because I’m so tired and don’t have the patience to listen to him cry.

So my question is: for those of you who pump at night, what do you do? Set an alarm for a specific time to pump and then do bottles only when baby wakes up? Or do you pump right when baby wakes up and give a bottle then? The problem with that is he will probably get too fussy waiting.. but I also don’t want to wake up just to pump, and then again to give a bottle. Any advice would be appreciated!