The main application we ship is pretty big and complicated. Currently, the only way to install it is through the installer. The installation is, from what I’ve been told, pretty complicated. Installing the application by updating binaries and restarting IIS is not an option.

Recently, a teammate configured the installer to run headless by passing a XML to it with all of the properties needed to install and we’ve been dogfooding it within R&D to help ease the burden of installing builds. I wrote a PowerShell script to connect to the server we want to upgrade and performs the installation. It’s designed to run connect to a server using a remote PowerShell session, copy the artifacts over, backup the database, update the database, then update the application.

Now that we’ve gotten this far, I’m trying to implement a set of tests to run post install and pass/fail the build based on these additional criteria (Did it install? Did it pass all the tests?). I’m trying to have the running, at least nightly, by the end of the year.