Vehicle in question is a 2001 Silverado with 4.8, RWD.

So, I've been trying to research this problem and nearly every video or Reddit post describes the issue as the compressor turning on and off randomly due to a faulty pressure switch, but that isn't what mine is doing.

My A/C blows ice cold when it is working. If I get up early in the morning when it's like 70 degrees out, it runs and runs and while driving about 10-15 minutes, it'll turn off and never turn back on. If the temp stays around the 70's and the truck sits for a few hours, the compressor will work again and repeat the same issue.

If the temp starts climbing to 80 and higher, the compressor will never turn on, even if it's at night.

I remember years and years ago when it would do it when sitting at a stop light, but when the truck got moving again after a minute or two, the compressor would cycle back on, but it no longer does that.

Could this still be the pressure switch failing or is it a problem with the clutch? I have not checked the relay yet, I'm going to check that tomorrow when it's light out.

 

It could be the due to a failing clutch coil or a weak clutch coil such that when it is "cold" the magnetic field produced by the clutch coil is strong enough to hold the compressor clutch in. Then when it heats up the magnetic field is not strong enough to pull the clutch in and hold it in position.

You could try to lessen the air gap of the compressor clutch to see if that helps. If it does not then you'll need to either replace the fan clutch and coil assembly or replace the compressor.

Good Luck!