How Does The New Hotmail Stack Up To Gmail?

This may come as a surprise, but the new Microsoft Hotmail is actually pretty good. But how does it stack up to Google's email champion, Gmail? Here's a look at the good and bad of both services.

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Where Hotmail Gets High Marks Inbox ZERO

The new Hotmail focuses heavily on reducing your cluttered inbox and keeping your email organised. New one-click filters let you focus on senders in your Contact List, social updates (via Twitter, Facebook, Linked In, etc.) and more.

You'll also find Quick Views useful when looking for certain types of emails, such as those that contain photos or documents or even shipping updates.

Conversation View feels a little late to the game as threaded conversations are a Gmail staple. However, if you prefer not to view your email messages as threaded, Hotmail allows you the option to toggle Conversation View on and off. The choice is welcome.

While these types of filters can be useful, the more exciting addition is Sweep. Sweep allows you to move or delete all messages from selected senders as well as tell Hotmail to automatically continue with the chosen Sweep action in the future.

While each of these features is technically possible via Gmail's search—and certainly more versatile—Hotmail succeeds in making every one of these actions both fast and easy to accomplish.


Hotmail has an elegant new way of handling attachments. Integrating with SkyDrive, Microsoft's free online storage offering, you now have the ability to attach up to 10GB of files per email. This probably sounds both incredible and excessive, and that's probably because the 10GB number is more of a marketing gimmick than a reality. While you could, technically, attach 10GB of files to an email you have a limit of 50MB per file and 200 files per message. SkyDrive also comes with a 25GB limit. Chances are you'll do just fine with these limitations, but nonetheless it's fine print to be aware of.

Attachments in Hotmail go straight to your SkyDrive and are sent as links to your recipients. Nonetheless your files appear just as you'd expect attached files to appear. Hotmail detects kinds of attachments, such as photos. When you send photos, Hotmail not only generates a gallery but a slideshow as well.

The new way Hotmail handles attachments is great but it's also very specific. It forces you to use SkyDrive and Microsoft's design for certain types of content. Power users may find this off-putting and favour Gmail for attachments, but Hotmail's new methods are a definite bonus for the average user or anyone looking for simplicity and ease.

Embedded Content

Hotmail introduces a new feature called Active View that embeds web content in emails. YouTube links come with thumbnails and can be played back within the message, Flickr links become photo galleries and LinkedIn requests can be accepted without every leaving Hotmail.

My personal favourite, however, is how emails with shipment tracking numbers are handled. Hotmail recognises the tracking number and displays the latest tracking information within the email. While most of these features are available in Gmail already (or via Labs), Hotmail's implementation takes it a bit further and is really well done.

Microsoft Office Integration

If Microsoft's own product didn't offer the best Office integration they'd have a lot to worry about. Fortunately, for them, they've done a great job of integrating Office into Hotmail. The new integration offers a lot more than just opening and editing Office documents; it also handles versioning, corrections, collaborative editing and seamless transferring of files between the web and desktop apps (if you're using a Windows PC, anyway) thanks to SkyDrive. These features get pretty in-depth, so if you're interested in the details Microsoft put together a decent overview (which requires Silverlight—yeah, yeah, I know).

Hotmail's Office integration is very well thought out and offers some noted advantages over Gmail and Google Docs, though it is worth noting that some features (such as collaboration) are available in Google Docs as well. Check out our comparison of the Office WebApps and Google Docs more information.

Where Gmail Holds Strong Speed

Although Gmail is fast, it's the speed in which it lets you work through your inbox that gives it a leg up over Hotmail. Gmail excels in getting out of your way. Hotmail, on the other hand, likes to sit and chat. Sending email in Hotmail, for example, displays a dedicated success page after sending. It prompts you to add the recipient to your contact list or network if they're missing from either. This may save you a step if you want to add people to your list or network but is an encumbrance if you don't. This is the general downside of Hotmail, in my opinion. It always wants to help you do this or that and inform you of every little choice it makes. While it seems this exists to assist the less tech-savvy in their foray into the world of email—which is a legitimate choice on Microsoft's part—the interruptions begin to feel relentless when all you want to do is reply quickly. I think even the most basic of users, should they have a fair amount of email, will find these interruptions annoying.


Google's a tough opponent to beat in search and they still win out here. While Hotmail's added search suggestions as you type to help find focused results, Google's search not only remains incredibly accurate but versatile in the search terms it accepts. Hotmail's search has improved, but Gmail is still very much the king.


Hotmail has a nice and generally attractive layout, and definitely isn't disorganised, but Gmail does a phenomenal job at organising your mail with filters and labels. Along with powerful sorting features, messages can easily be identified by type and status based on colours, shades and labels.

Instant Messaging

Hotmail's late to the party with IM, and you're required to use MSN Messenger. Though it offers nice features like tabbed messaging and SMS, Gmail is still far ahead with audio and video chat and AIM support.


With this new release, Hotmail introduces a better app for the mobile web (primarily the iPhone). Still, it has yet to match the functionality of Gmail on a mobile phone. Additionally, Gmail not only performs well as a web app but integrates beautifully into the Android mobile operating system. While we may see a great implementation of Hotmail in Windows Phone 7, it's not here yet.

Where it's a Draw: Spam Filtering

Microsoft made big strides when improving spam filtering in Hotmail. They call it SmartScreen and it implements a number of spam filtering features that have been present in Gmail for some time. One method used is the record of spam messages and spam senders that is generated by Hotmail users, allowing commonly reported spam messages to be automatically filtered out of everyone's inbox. SmartScreen also scans message content to try and determine if it is spam or not, checking sender IDs and whether or not if the message is authenticated. This is all welcome but nothing revolutionary.

Where Hotmail takes it a step further is with your interaction, and this is both a good and a bad thing. Hotmail will track your behaviour with certain messages and make relevant suggestions. For example, if you're frequently deleting messages from the same sender without reading them, Hotmail will suggest that you unsubscribe from their mailing list. If the sender does not honour your unsubscribe request then Hotmail will suggest you block that sender. While this is certainly smart and sounds nice in theory, in practice you're being pestered by Hotmail with some regularity. Because Hotmail likes to interact with you, make frequent suggestions and constantly keep you abreast of every choice it makes on your behalf you may feel like getting from point A to point B is more work than you'd prefer.

One of Gmail's best features is how it gets out of your way and allows you to concentrate on your email. Because this extends to spam filtering, which requires a little as marking a message as spam on the rare occasion Gmail doesn't catch it for you, I personally favour Gmail's spam filtering. Hotmail, however, does offer some smart new features for dealing with messages that lie in between spam and regular mail (Microsoft calls these messages "gray mail"). While it's not for me it may be for you, so I say it's a wash.

It's worth noting that we love Gmail here at Lifehacker, so while this is was an attempt to be fair and even-handed we may often favour Gmail because, well, we like it. Nonetheless, there are some great new additions to the new Hotmail and things are still missing from both. What would you like to see in future iterations? What do you like about existing features? Let us know in the comments.


    Sorry Microsoft. Lack of decent mobile out there (SMTP is a *must*) means i'll be sticking to Google. Pity since I did want to move my email to you using Live Domains...

      @Thomas Hambleton: Hotmail had SMTP/POP3 support for a long time. The new version is said to have Exchange ActiveSync support too for mobile phones.

    Are they still appending ads to the end of hotmail emails ? uggggghhh

    I have been amazed/annoyed at the ads appended to the bottom of Hotmail users emails for many years now. Sometimes borderlining on crude or at least WAY out of context "Meet singles in your area". Who would choose this? Do they still do this? Friends and colleagues sending you ads, unbelievable.

    What, STILL no sync with alternative mail clients (i.e. IMAP)? Pfft!


      Seriously... Where is the IMAP support?

    Microsoft have announced on the Hotmail blog that they are removing those tag lines from their emails form this version on.

    In the past this was a very valid marketing approach, now days it's a little redundant and thus has been removed :)

    @Thomas Hambleton - You clearly haven't had a play with the updated mobile hotmail.

    @Tim - Windows Live Mail gives you access to synching. It's a great client which I use day in, day out :) Worth taking a look.

      Thanks James, but as a Mac user I'm still left out in the cold. Most frustratingly, they've allowed ActiveSync over wireless devices (i.e. iphone, android) but I want a solid DESKTOP client for my hotmail. Give me an Entourage or solution and I'll be happy, Microsoft!

      p.s. For those who want Hotmail on their wireless devices, it's active now for all, whether your account has been upgraded or not...

    Hotmail still can't do filtering of incoming emails into folders.

      You can tell hotmail is from an American company; where else would a company feel unashamed enough to use such twat to users from throughout the world? And the joke is that I get more junk with my hotmail account than with any other service. I only use hotmail when I have to provide an email address to register online.

      What? I've been filtering email to folders for years and years and years with hotmail...

      Well it is there but the functionality is obscurely hidden in the settings area so most people probably don't know, but it is there.

      I've only recently started using gmail, but it seems to be extremly slow when expecting to recieve emails. Hotmail has always been almost instantanious.

    I would like to try it.

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