The Electronic Frontier Foundation has some good perspective:
Microsoft debuted the always-use-HTTPS feature for Hotmail in December of 2010, in order to give users the option of always encrypting their webmail traffic and protecting their sensitive communications from malicious hackers using tools such as Firesheep, and hostile governments eavesdropping on journalists and activists. For Microsoft to take such an enormous step backwards-- undermining the security of Hotmail users in countries where freedom of expression is under attack and secure communication is especially important--is deeply disturbing. We hope that this counterproductive and potentially dangerous move is merely an error that Microsoft will swiftly correct. The good news is that the fix is very easy. Hotmail users in the affected countries can turn the always-use-HTTPS feature back on by changing the country in their profile to any of the countries in which this feature has not been disabled, such as the United States, Germany, France, Israel, or Turkey. Hotmail users who browse the web with Firefox may force the use of HTTPS by default--while using any Hotmail location setting--by installing the HTTPS Everywhere Firefox plug-in.
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