At my day job, I primarily deal with Microsoft products, and of those, my main project is implementing Office Communications Server. I had rolled out a stripped down version of OCS 2007 back around Christmas, and in February Microsoft released OCS 2007 R2. The difference between the two versions is not worth going into here, but they did change some substantial infrastructure elements with the upgrade.
As I was installing the 2007 version, I wanted to gouge my eyes out repeatedly, as the process to get the servers installed was painful to say the least. I was hoping they would fix at least some of this with the 2007 R2 release, but no, it is still just as painful. To sum up most of the frustration, I will say that the installer looks like an easy step-by-step walk-through, but there was a theme that kept recurring as I experienced this installation. You have to run different sub-steps of the installer from different servers under different usernames (Active Directory domain admins, schema admins, local administrators, etc.), and the error messages hardly gave a clue.
Anyway, I won't bore you with too many details, but I did come across two particular screenshots that I thought were funny. In true This Is Broken taste (which has moved to Good Experience since I was actively following it), here are two screenshots that show that OCS is written sloppily, and is simply "broken".
There is plenty more I could write about with regard to this product, but I thought those two pictures summed it up pretty well.