Here's how the logic works: MSFT does business in these countries. These countries have a sudden desire to monitor some citizens' communications (which include Hotmail accounts). HTTPS prevents this monitoring, so these countries lean on MSFT. Ergo, MSFT shuts down HTTPS access to Hotmail.
For a lot of these regimes, it's a matter of survival to crush dissent. MSFT just made that a little bit easier.
Let's say there are two options to consider: 1. There is a localization bug that affects the always-https setting. 2. Microsoft wants to do business with those countries and purposefully created a defect in always-https.
The first case is very plausible (to me at least). Defects happen, some are more visible than others.
The second case is less plausible to me. The current pattern of governments is to request by local-law the ability to monitor/control communications without the citizen knowing. An example similar to this hypothetical that is often in the news is countries that request a Blackberry messaging server in-country.
Q: Why would Microsoft collude with these regimes to crush dissent in such an obviously noticed and easily defeated way?
A: Because their evil regime assistance unit is incompetent.
Q: Why would you choose that over the more simple first case of a localization bug?
Governments buy truckloads of licenses and get to determine how much tax you pay. I'd say it would be completely unlike Microsoft not to have them. Their sales force is not the kind of people who would leave money on the table.
I've seen how government sales are made. There is a lot in common with sausages.
If MS sells them Windows and Server products, then it is not out of question.
Perhaps with so much to keep up with lately the NSA monitoring equipment is struggling to MITM that many TLS sessions, so MS cut them a break.
(mostly kidding...)