Microsoft Ups Its Email Game With the New

There was a time, long ago in the mid-1990s, when Microsoft was the leader in email. Everyone who was anyone had a hotmail account. I remember mine well. It was [email protected] and it was my first foray into electronic mail.

The web has come a long way since those humble beginnings of the email awakening, and a lot has changed. I moved from Hotmail to Yahoo! Mail, then was a fairly early Gmail user (early 2004- thank you, dear Blooger account for getting me early access) and I’ve been on there ever since. As a matter of fact, I feel everything pales in comparison to Gmail. But when I found out that Microsoft was launching as a brand new email service,, I was curious and signed up. Let’s see what I found. Not Your Father’s Outlook

Note: You can easily convert your Hotmail account to the new Outlook, and can even still get an email address as an alias. Some screenshots provided by Matthew Guay are at the bottom, below the Conclusion.

Right off the bat I’ve got to say I love the Metro look (now known as the Windows 8 style UI); it’s clean and easy to understand. I was very happy to see that Outlook has applied that look- it makes email look clean again. Nothing against Gmail, but my Gmail account looks like Grand Central Station it’s so busy. Outlook is a refreshing change.


The inbox, as you can see, is simply one blue bar across the top, a sidebar, and your email. When you select an email, some new buttons are revealed. By clicking the New button, you can compose a new email, which to recipient information on the left and the writing area on the right. Again, this is really clean.

Compose an Email

Ok, you get it: Outlook is clean. But is it functional? Let’s take a look.


So how well does Outlook work? Like I said, out of the box it’s a really simple, intuitive interface with the core functions- Inbox and important links, Compose (New), and Search readily available. Clicking on an email will bring up the cotent as well as some context buttons for the typical email funcitons: Replay, Replay to All, Forward, etc. There is also a pretty interesting feature called “Sweep.”



Sweep will let you move or delete all messages from a particular sender very easily; this is really nice if you want to say, delete the massive amount of emails Facebook seems to send every day. You can also schedule cleanups, which seem to be similar to Filters in Gmail, and pretty robust. You can also create your own rules for Sweeps based on certain criteria.

Create Rules

You can even have Outlook only keep “the latest message” from a sender.

Schedule Cleanups

Another pretty neat feature of Outlook is the Quick views categories, featured in the left sidebar.

Quick views

Quick views serve as a sort-of favorites section for categories you want to get to, well, quickly. By deafult, there are a few interesting categories:

  • Documents, which appears to include most emails with attachements (automatically).
  • Flagged, which serves as a single place for any messages you flag. This is similar to the starred emailed in Gmail.
  • Photos, which will include any emails with image attachements (automatically).
  • Shipping updates, which I think is the most interesting. This one will automatically scan the text of your email for indications that something you ordered has shipped. Very cool.

With the combination of Quick views and Sweeps to create rules, you can finely tune your mailbox to really make it work for you. I’ve done the same thing in Gmail, but it looks really great in Outlook; it feels a lot less overwhelming and I really like that.

Other Features

Microsoft has also integrated other features from Hotmail into Outlook. One is what they are now calling, “Messaging.” This is similar to Google Chat, though a nice feature is that you can connect it to Facebook to chat with Facebook friends right from your email. That said, this service didn’t seem to be working when I tried it.

One of the things I love about Gmail is its advance search queries/selectors, and I was curious to see if Outlook had similar ones. It turns out that it does have a few, namely to:, from:, and subject:. You can also do an advanced search for attachements, keywords, dates, etc. The advanced search worked surprisingly quickly when I tried it, where as the sidebar search sometimes didn’t work at all. I thought that was strange, though I’ll attribute it to growing pains/Outlook still being in beta.

Advanced Search


Outlook also has a ton of great settings to really customize your email experience. From the top nav bar in your inbox, you can do things like change the color scheme, adding a reading pane, and ask for help/offer feedback. Clicking on “More mail settings” will take you to this page:

Settings Page

While I won’t go through all of the settings, I do want to point out a couple.

  • Sending/reveiving emails from other accounts: One of my favorite parts of Gmail is that I can use it as a hub for all of my inboxes, having all mail sent to it and being able to respond using any of my email addresses, not just my Gmail one. I’m glad to see Outlook has also added this funcitonality.
  • Create a Outlook alias: This will allow you to create what is essentially a separate email address that goes to the same account. This coupled with Sweeps/rules can serve as a great way to manage mailing lists or services you want to keep out of your main mailbox.
  • Rename your email address: On the same token, if you decide you’ve outgrown your current email address, you can change it. But don’t worry, you can decide what happens to the email that goes to the old one.


All in all I think Microsoft did a really great job with Outlook. It’s clean, easy to use, and has some very nice features. Hey, if I find I prefer Outlook’s interface over Gmail’s, I can essentially use my Gmail account through Outlook. Also, as a note, I did everything using Google Chrome on a Mac, so I don’t think we have to worry about lack of major browser support.

Did you start using Outlook? What do you think? How does it compare to your current primary email client/service?

Hotmail Upgrade Screens

As promised, here are a couple of screenshots from the Hotmail -> Outlook upgrade process

Microsoft asks you to give Outlook a try!

If you didn’t get the above prompt or decide to try it later, you can upgrade via the Options menu.

Here’s Outlook welcoming you into it’s warm embrace!

Summary is a new email service offered by Microsoft; it's a free upgrade from Hotmail and Live accounts.