Custom Windows Instance on AWS OpsWorks

Spent today trying to get a custom Windows-based AMI instance to work within AWS OpsWorks. Here are the steps that worked for me:

1. Launch new Windows 2012 R2-based instance (in our case it was the MS 2012 R2 w/ SQL Server 2014 Web AMI)
2. Log into new instance and run EC2ConfigService Settings
3. Navigate to “Image” tab
4. Choose “Random” under “Administrator Password”
5. Click “Shutdown with Sysprep”
6. Wait for instance to shutdown and then create AMI from it (Right-click->Image->Create Image in the EC2 Instances Console)
7. Create a new OpsWorks stack (choosing “Microsoft Windows Server 2012 R2 Base” or “Use custom Windows AMI” for the “Default operating system”)
8. Create a new layer in your stack
9. Add a new instance to your layer (choosing the AMI you created in Step 6 under Advanced -> Operating system)
10. Start your new instance
11. Wait to see instance status change from “booting” to “running_setup” (may take quite some time, 20+ minutes)

Hope this helps someone else. The part I was missing originally was steps 2-5 which resulted in the OpsWorks instance starting but failing to configure and remaining in the “booting…” state.