Sam Gentile thinks that MS is at a crossroads in terms of web development.

He thinks with all the cool, free, cutting edgs stuff out there, like Ruby on Rails, MS may soon lose out on all the “alpha geeks”, who move on to newer and better things while MS stays locked in the past.

I’m not ready to crown RoR the winner of anything yet.  True, MS is usually not on the cutting edge, but they usually do a pretty good job adopting good ideas.  There are only a handful of serious RoR sites out there.  If that number grows a ton, then it will mean something. 

Martin Fowler has some similar concerns though, so maybe this will come to fruition.