I recently bought a new domain name for a side venture, and registered for a free email with domains.live.com. It is the hosted domain equivalent of an Outlook.com address. The premise is identical to Google Apps for Your Domain (GAYD). But, because GAYD is no longer free, I decided to give Microsoft’s alternative a chance. It excelled in document creation and editing (as one would expect from the creator of Microsoft Office) but the e-mail couldn’t keep up with Google.


Don’t get me wrong. The interface for Outlook.com and its hosted counterpart is slick. It loads quickly and it’s easy to navigate. There are “Quick views” preloaded to easily find photos, documents, or shipping information in e-mails. There is a search feature and archive feature, as you would expect. The e-mail window even lets you chat directly with Facebook friends or MSN messenger contacts.

The Outlook.com mail also has a reading pane, which will be familiar to anyone that has used Microsoft Outlook on the desktop. And users can set up other addresses as “send from” accounts. But there is no way to automate different signatures for each account like you can with GMail and GAYD.

Overall, I like the interface and enjoy using the web client. Unfortunately, where the Windows Live hosted e-mail falls unforgivably short is the lack of IMAP support. The system only supports POP access. This means that there is no two way synchronization between inboxes. If you use a desktop client and it checks your e-mail, that e-mail is pulled from the server and either deleted or marked as read. The same applies to your smartphone. That means you can’t move an e-mail to a folder, or mark it as unread from your phone.

In 2013, this lack of support is astonishing. Back in the day, it made sense to use POP for e-mail access. If everything stayed on one computer, that’s all anyone needed. The inbox was treated as an inbox, and e-mails were printed or archived from the inbox. But now we check e-mail on the go and need to have access to it from different machines. We need to be able to categorize, flag, and move e-mail while keeping it synchronized across devices.

Thanks to commenter Avi Frisch for pointing out in the comments that Outlook.com supports Exchange ActiveSync. This is great news. I had only been searching for IMAP and forgot to research ActiveSync.

Editing Documents

Like Google Apps, Windows Live offers cloud-based document editing. Unlike with Google Apps, former Microsoft Office users will feel right at home. The interface is almost identical to the regular Office suite. And, unlike Google Apps, Office documents are uploaded with little to no formatting issues.

But if simplicity is your goal, you won’t like Microsoft’s online document editors. Like its Office suite, the online editor tries to give you access to many tools. Unfortunately, this results in a cluttered work space.

Calendar and Contacts

The calendar worked pretty much as expected. Adding events and inviting people is simple. But the calendar is not searchable. This sounds like a minor gripe, but I rely heavily on Google Calendar’s search. When clients call, I can quickly search to find out when their next hearing is. And at tax time I search for different meetings to make sure I didn’t miss any deductible mileage. The idea of losing that feature was tough to swallow.

Contacts were also intuitive. Outlook allows you to link your Google Contacts, Facebook friends, LinkedIn connections, and Twitter accounts. I don’t see the point of Twitter, so I didn’t bother with it. But my Facebook friends’ contact info was imported, including e-mail addresses. Their birthdays were added to the calendar automatically, which was nice. But if you don’t want their birthdays added, it seems you are out of luck. Once the account is linked, I could not find a way to hide Facebook birthdays.

Annoyingly, this created a lot of duplicate contacts. Anyone I already had in my Google contacts that I’m friends with on Facebook had two contact cards. Luckily, there is an easy-to-use feature that lets you merge duplicates very quickly.


After only a week with this account, it’s too early to ditch my Google Apps accounts. SkyDrive definitely makes it tempting. The integration with Microsoft Office is very easy. The contact linking is also a nice feature. And, unlike some Facebook integration services, Microsoft pulls your friends’ email addresses.

Unfortunately, the e-mail is a dealbreaker. I check my e-mail on my phone, my tablet, my laptop, and my desktop. Sometimes I use native clients, sometimes I use the web app, and I even use the occasional third party client. I need all of these to sync up and let me organize my messages into different folders. Coupled with the lack of a searchable calendar, Outlook.com isn’t ready to replace Google Apps quite yet.

As I stated above, the e-mail is no longer a dealbreaker. With Exchange ActiveSync I can keep everything organized the way I like. The idea of switching is still tough with no searchable calendar, but much more appealing.

6 responses to “A Week with Outlook.com”

  1. Kash Khan says:

    There is an Outlook.com app for both iOS and Android that was just recently updated to look and function exactly like the website. It also syncs with the phone’s built in calendar.

    Additionally, you can setup a Live Domain email using the Hotmail settings on your mobile device/computer, and you essentially get IMAP- like features in your native e-mail app.

    Yes, it’s not as intuitive as Google Apps, but once you figure it out, Microsoft’s offering works extremely well. I’ve been using Live Domains for my firm since January and it’s been great.

  2. Avi Frisch says:


    Outlook.com supports exchange activesync on both desktop and mobile and it syncs calendars, contacts and email. Whether you like other aspects of gmail is for you to say, but it is misleading to say that you cannot sync your emails on your phone.

    • Josh Camson says:

      Thanks Avi. I had only looked into IMAP, and not ActiveSync. I appreciate you pointing it out. I’ve changed my account on my phone and updated the post. Are you using Outlook.com as your main e-mail provider?

  3. Avi Frisch says:


    I use outlook.com for my personal email, having switched from gmail about a year and a half ago (when it was still hotmail). About four months ago, I switched from Google Apps to Office 365 for my business email and have largely been happy ith the switch.

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