It appears that Microsoft will not continue to fund IronRuby. Hopefully it will continue to flourish as a community project; I wish them luck. This does raise the question of whether IronPython will meet the same "fate"; in the absence of word from the IronPython team (it is the weekend, after all), I think I'll indulge in some wild speculation.
Mr. Schementi's last day at MS was July 23, meaning he probably gave his two weeks' notice an July 9. Thus, the writing was on the wall by the and of June/beginning of July. That's my rough timeline. But, something doesn't fit.
On July 1, Enthought announced that they would be porting NumPy and SciPy to IronPython and .NET. I would imagine that they would have gotten some assurance from Microsoft that the IronPython project would continue. Or, they've gotten shafted - it happens.
My hypothesis - that IronPython will continue to be funded, for now. The team has said that there are/were potential customers within Microsoft (the Dynamics team was one, I believe), which is critical for continued support. However, I believe there may be one other unexpected saviour - the Windows High-Performance Computing (HPC) team.
Python is the scripting language of choice in the HPC community, largely because of the NumPy/SciPy libraries mentioned earlier. I wouldn't be surprised if Microsoft was making a push to get Windows and .NET deeper into that space (it's small but profitable), and IronPython with NumPY/SciPy support could be a key part of that play.
Also, both teams had releases on July 16th – IronRuby 1.1 and IronPython 2.7 Alpha 1. I think that Alpha is an important signal of the team's expectations.
This is what happens when I have insomnia. Hopefully this will still make sense in the morning.