Hi @Rafe Kemmis , I understand that you have several App Services using ASE v2. You are trying to enable Health checks but some of your App Service plans do not have Health check option available.
I think you referred to this document about Health check not supported on ASE v2:
Does Health check work on App Service Environments? Yes, health check is available for the App Service Environment v3, but not for versions 1 or 2. If you are using the older versions of the App Service Environment, you can use the migration feature to migrate your App Service Environment to version 3.
Could it be that your dev/staging environment uses Free or Shared App Service Plan? Or has it been upgraded to ASE v3? Does your ASE use ILB (Internal Load Balancer) or ELB (External Load Balancer)?