I deploy Tekpub, on average, 3-5 times a week. This used to scare me every single time I did it - for various reasons: no rollbacks, I’d overwrite some of Avery’s changes, I’d forget something. Imma go ahead and say it: ASP.NET Deployment is a joke.

I agree with Rob that the state of deployment for ASP.NET applications is lacking. Issues arising from deployment is something that the team I work with continually have to deal with. It seems that the build and deployment tools that Microsoft provides are so complex that it requires a dedicated person solely responsible for managing them. When we moved to Team Foundation Server 2010 we wanted to incorporate deployment as part of the build process. However, trying to adapt Windows Workflow to a custom build process is an absolute nightmare. I’m not saying having an automated build and deployment process is trivial, but it doesn’t need to be that complex.