Via Steve Jacobs: The Communications of the ACM has an analysis of what happened to OLPC. It has a lot of generalized statements - I'd like to have seen it backed up by more specific stories - but it is a good summary, as far as I can understand it.
Information technologies are not standalone innovations but... socially embedded systems, the use of which cannot be isolated from the social and cultural environment or from local norms of practice... The fact that OLPC was much stronger in developing innovative technology than in understanding how to diffuse it may reflect the engineering orientation of the organization and its lack of understanding of the needs or interests of the nontechnical people who will ultimately buy and use the innovation.
I'd also like to see a similar thing written on Sugar Labs (now that it's nearing its one-year anniversary) by someone with an MBA-like mentality who can step back and see more of an operational picture rather than just technology or education alone (though "learning" has to be the metric of success, somehow).
As an aside to the students and alumni of my alma mater: I'm deeply thankful for the education I got at Olin. It didn't necessarily teach me everything about how to make innovative technologies or how to diffuse them (what academic program can?) but it did teach me that I needed to learn both, and gave me the tools to do so. I feel like I can absorb a lot more learning from experiences like working on OLPC because of the things my undergrad years gave me to reflect on. Working on these kinds of things definitely showed me why our profs tried to teach us the way they did.
Finally, I do agree with this comment from Julian Bass:
The OLPC appears to prioritise a technocratic solution to what is essentially a social problem. Large scale educational change requires a social movement.
...and I suppose that's why I've moved into community work over the past few years, though I didn't realize that was what I was doing for quite some time. Sometimes you need to do technology work because the tools that people need to change things don't exist. Sometimes you need to do policy work because they're not legally allowed to. Sometimes you need to do journalism and marketing because they don't know about it. Sometimes you need to do education work so they can teach themselves to understand. Sometimes you need to move between them all (and more), busting bottlenecks in whatever disciplines they come up in.
It's interesting to watch people and organizations adapt to better save the world.