Interessante

Microsoft Shuts off HTTPS in Hotmail for Over a Dozen Countries (Electronic Frontier Foundation):

Microsoft appears to have turned off the always-use-HTTPS option in Hotmail for users in more than a dozen countries, including Bahrain, Morocco, Algeria, Syria, Sudan, Iran, Lebanon, Jordan, Congo, Myanmar, Nigeria, Kazakhstan, Uzbekistan, Turkmenistan, Tajikistan, and Kyrgyzstan. Hotmail users who have set their location to any of these countries receive the following error message when they attempt to turn on the always-use-HTTPS feature in order to read their mail securely:

Your Windows Live ID can't use HTTPS automatically because this feature is not available for your account type.

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. 

[Isto aconteceu durante pouco tempo - essa opção já está funcionar nesses paises; pelos vistos tratou-se de um bug]