In the comments, Robert Scoble asks what could they build that +would+ convince you [that Windows is better than Linux for a server]? It won’t be easy, but Microsoft needs to take the next step in trustworthy computing: Trustworthy Design.

True or not, Windows is perceived to be a complex furball of code. Patches to fix problems in one area create surprising new behavior in other areas. Fixing a Buffer Overrun in Kernel Message Handling can slow your system to a crawl. As a consequence, Windows is perceived to be less stable that Linux – not because of the relative numbers of bugs, but because of the complexity and ramifications of the bugs.

Microsoft needs to build trust in the design of Windows: trust that complexity is managed by good design and trust that components are isolated from faults in other components. Actions speak louder than words. And acts like embedding IE tightly into the OS speak quite loudly.