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So I ended up figuring this out myself.
When I did sysprep and created the first AMI I'm positive I selected to generate a random password but no matter what I did I could never get a password to generate. I also noticed that when I was using terraform to try and stand the server up the script that I specified under user_data wouldn't run. I went ahead and created a new AMI from my base image and this time selected random password and also checked the box to Enable UserData execution for next service start and did another sysprep with generate random password checked. After creating an AMI from that machine the random passsword would actually generate so it appears there may be a bug where random password doesn't work unless you also enable User Data