If you're struggling with quick disconnects (QD), then you're not alone. I have been brewing for years and I fight with them nearly every time I hook up a keg. I keep thinking there's a secret I'm missing, but I just can't seem to find it.
Make sure the poppet on the post is depressing smoothly - use a screwdriver to push it in. It should have resistance but not too much. It should also be flush with the post, not proud.
When you attach the QD, pull up on the sleeve first, place it on, lower the sleeve, twist a bit to ensure that it's seated, then lean on it with the butt of your hand. Fail? Keep trying. May need to re-seat it a few times.
I'm interested if others have better tips for us on this.