When I debug a web application, the web.config transforms are not applied. I simply find that the configuration in web.config is not applying the transform for the configuration I'm currently using.
Yet if I build a deployment package then I find that the web.config does have the current transforms applied.
Are transforms not applied when debugging? I'm starting to wonder if this is the case, but I have coworkers insisting that it works for them.
Web.config transforms are only applied when publishing or deploying.
Jared Harding provided a link where a member of the .NET Team answered this question in the response here: VS2010 Clean Web.configs - not updating
The link he provided for ease of reference is: http://forums.asp.net/p/1532038/3711423.aspx
You can start a transform by introducing a "AfterBuild" entry in your project file as described here. Downside: you have 2 web.config files...
http://kfigy.blogspot.ch/2010/03/making-visual-studio-2010-webconfig.html