I’ve been working on being able to use Octopus Deploy to deploy ASP.NET Core applications through IIS and I was faced with an interesting challenge. When publishing to a File System through the Visual Studio Publish command, it will trigger a PowerShell script that essentially will call Microsoft Web Deploy V3 (msdeploy) to put your FileSystem up to date with your release. But before calling MSDeploy, it will update (or should I say overwrite) your web.config with the proper handlers that match your application. This means that it will create a generic web.config and removing all the settings you may want. The ASP.NET team is aware I believe of the fact that the publishing tool is limited and thus in need of some customization features…