Mine does yes, found conflicting information on the matter in gm's documents, one document says it should everytime and another say's it is normal for it to not turn on everytimeAgreed. Should be calibrated for whatever weight is normally in the vehicle.
Related: does your guys’ air suspension compressor kick on every time you start the vehicle? I literally never hear mine. And I’ve got realitivly new rear air shocks.
*that is part of the reason why I ever even messed with mine, the compressor wasn't coming on everytime and the shocks had a slow leak, so I just replaced both
I would say if your pump does not turn on everytime then there might be something wrong, if you have a tech2 and run the alc trimset you should hear the pump release the air, if it doesn't then the release valve may be bad and it's just holding air and therefore never needs to come on. just my guess... I think you can test the valve with the tech2 also in the same menu
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