Just reporting back on my findings. Thanks again WyrTwister for the awesome tips. Very helpful especially someone like me that is no too savvy on a/c work. I put some dye in the a/c system and saw a leak near the connectors on the compressor. I installed new o-rings and followed your advice. So far it's working great! It has been a week and so far no problems with brakes. Problem solved??? I wouldn't call it that just yet since the problem was intermittent and had no set pattern. But it looks promising so far. I did keep the old brake booster hose and did a little research with a hand vacuum pump. It turns out the valve would get stuck when vacuum was applied. Another words when I applied vacuum to the booster side, vacuum holds. Now when I apply vacuum to the intake side of the hose I got a vacuum! This just happened once and after that the valve operated normally without fail and air flowed freely. So my theory is.. if the valve wont open when vacuum is applied then that would cause the problem we've been having with loss of brakes. As I said I won't call this "problem solved" just yet. If the brakes works for a month without fail then it's fixed! I hope this information helps people who comes across this problem. I've done some Googling on this subject for a while and it seems like a common issue. Could this check valve not opening up as it should be the root cause of this? Hhhmmmm.. Was installing a new brake booster and master cylinder was a waste of money?? Well yes and no.. The car is 11 years old and I can rest easy knowing the car has all new brake system. Also I don't feel as bad knowing the GM tech did catch this either. Probably good for another 100k miles. Plus brakes is not something you want to skimp on either. If any one has any questions let me know. I will report back again if I find anything else.