What Microsoft have done is provide example integration in the form of IronPython Studio, which frankly sucks. Many important features are fragile, broken or missing altogether. Good IDEs like PyDev and Wing do provide these features, so it is definitely possible - it just requires a lot of work from scratch.
Now they have a good platform for dynamic developers to use, which they give away free, but the tools they charge for don't really support them. This puts them in a position of either bringing developers to their platform but not being able to make any money, or having their existing developers stay with their platform but losing dependence on the toolset. Neither option looks much good for Microsoft.
(NOTE: for those who can't wait for official Microsoft support and have Visual Studio 2010, try Jeff Hardy's IronPython for Visual Studio Extensions.)
Anyway, K. Scott Allen sees things a little differently and I understand his frustration:
Consider this …Of course here we are talking about Microsoft as if it was a single entity with a single intention. The reality of course is that Microsoft is a huge company with many divisions and even more individuals working there. In all likelihood the vast majority of Microsoft employees have never heard of IronPython. The relevant division is the programming languages group, which includes Visual Studio development, and where the majority of employees who are developers probably have heard of IronPython if not actually used it... Adding official dynamic languages support to Visual Studio would require substantial investment of time and effort, so even if everyone in this department was determined to add support it would still be dependent on forces from other parts of the company who have other needs and priorities...
IronPython got underway in July of 2004. Five years later it appears IronPython is still not a candidate to be a first class language in the .NET framework and tools. You can vote on this issue.
Microsoft first released IronRuby at Mix in 2007. Nearly three years later it appears IronRuby is still not a candidate to be a first class language in the .NET framework and tools. You can vote on this issue.
A first class language is deployed when the full .NET framework is installed. It’s as easy to find as csc.exe. It’s not a language you have to ask the IT department to install separately. It’s not a language that requires you to jump out of Visual Studio to edit or run.
Most of all, a first class language doesn’t require justification to higher powers. A first class language is pre-certified and stamped with a seal of approval. It’s as easy to use in the locked-down big corporate setting as the company paper shredder.