Another (OT) question. '99 chevey silverado

The engagement of the 4X4 system is even under 'puter conrol.

It looks at ABS (wheel speed) information, etc., before commanding the shift motor to engage.

You need to pull the trouble code(s) and see what the computer is "seeing" that it doesn't like... missing sensor information, or problems with the switch in the motor that tells the 'puter where it's at, for example.
 
Both my brother and I had the same problem on our 99's (one chevy, one GMC). The push button module for the four wheel drive will need to be replaced. I think when I did it a few months ago it was like $30.
 
Yes , it does have the buttom for the auto 4 X 4. I have never pushed that button. I do like the sounds of that push button modual replacement idea. That sounds like a simple fix to me. Sometimes when I go to switch from 4 wheel drive and back , I may have to do it 2 or three times before it changes. Still open to other opinions.
 
Before throwing money at it, get it "scanned". The 'puter will tell what's bothering it with a specific trouble code.
 
P.S....

What you are describing sounds more like a shift actuator unit failing. That is common. There is a motor in there, and a wiper switch that tells the 'puter that the motor has actually completed the commonded shift. If it doesn't shift, or takes too long, the 'puter turns on the warning light.

The shift buttons actually don't switch any current, just send commands to the 'puter that does the actual shifting. NOT to say the buttons can't fail, but it's not like they are actually carrying the current for the shift motor.

Replacement transfer case shift actuators are in the $125.00 to $250.00 range, depending upon rebuilt or new.
 
The button panel has a high rate or replacement on those trucks. I had the same issue with my 01. New panel and the problem went away. Had a buddy that worked at the dealership and said 75% of the problems are with the button panel on the dash.
 
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