Server 2008 32 Bit Password Not Available

Question

Instance ID: i-01e25f6fb84f7d4a7   
  
This instance was created from a custom AMI that was built by using EC2ConfigService to shutdown with sysprep while having it set so a random administrator password will be generated.  
  
When I stand up an instance using this AMI and I go to retrieve password I get the message:  
Password is not available.  
Please wait at least 4 minutes after launching an instance before trying to retrieve the auto-generated password.  
  
I've tried starting multiple instances using this AMI and they all have this issue. Why is it not generating a password?

Answer

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

Server 2008 32 Bit Password Not Available

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