Configure the "Connect with HTTPS" settings for your Hotmail account

An earlier tutorial gave you an overview of the Hotmail Sign in options and security settings; in this tutorial, we will focus on a new security feature the Windows Live team has released to all Hotmail users, which called "Connect with HTTPS". This feature is still new, and using it comes with a few caveats, but you'll be up to speed by the end of this page. In theory, you should absolutely use this feature - in practice, it depends on your case (see first section below for more details). Note that the latest version of Hotmail always uses a secure, HTTPS connection for the Sign in screen, login process, and select account configuration pages, and then optionally reverts to unencrypted "HTTP" for other, more mundane pages.

Tip: you may have heard of "SSL", which stands for Secure Socket Layers - a technical term to designate a safe and encrypted connection between your web browser and the website (web server, really) whose content you are using or looking at - in plain English, this is when you see a padlock icon in the address bar. "HTTPS" basically means the same thing - with a securely encrypted internet transaction, you'll see that everything starts with "https" in the URL:

A secure HTTPS connection in Windows Live Hotmail


Overview and limitations of "Connect with HTTPS"

You can check your Hotmail account from a web browser, from an email program (like Microsoft Outlook or Windows Live Mail), or both. If you only, or mainly, login to Hotmail from a web browser (Internet Explorer, Firefox, etc.) turning on the Connect with HTTPS setting is a no brainer: doing so will make your webmail experience much, much more secure - it will be "encrypted" at all times.

If you mostly check your Hotmail account from an email client, however, you will first need to test if "Connect with HTTPS" works without hiccups. There is no point in turning on this security feature if it prevents you from checking your emails altogether! But as you'll see, enabling or disabling it only takes a couple of clicks, so it is definitely worth trying. Because of its popularity, Hotmail (like Yahoo Mail and Gmail, really, and any other popular online service like Facebook) is often the target of hackers.

This is all it takes to enable HTTPS at all times for your Hotmail account; next time you check your email messages from an email program, keep in mind that you are now using the most secure Hotmail configuration. If you are receiving weird, "Cannot login to mail server" or "Cannot authenticate"-type error messages, you may probably need to disable HTTPS until your email client is updated.

Tip: Microsoft has recently added support for HTTPS to check Hotmail from Microsoft Outlook. Learn more in our tutorial on Outlook Connector + Download. In early July 2011, Microsoft added support for SSL in Windows Live Mail.

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