If I file 2 claims in less than 2 years, will my insurance think it is fraud?

Last year, I filed a claim after I had some jewelry stolen. I changed companies after that and specifically insured some of my more expensive jewelry. Recently, I lost a diamond bracelet - one I had specifically insured. I am worried about making a claim for a couple different reasons. I had one similar not too long ago, and also I feel like I was bit negligent in losing it. Will the insurance company think I am making a fraudulent claim? Will they cover it if I lost it due to my own negligence? What happens if I find it after the fact?

It depends on that specific writings of your policy. What you're talking about, "specifically insured jewelry" is referred to as a scheduled item. If your scheduled jewelry is covered for "mysterious disappearance" then you should be covered for this incident. In terms of your insurance company thinking it was fraud, I can't answer that. It's in the claims department's nature to be investigate any claim but that doesn't mean they will assume you are being fraudulent. I recommend being straightforward with them. Best of luck.