Why I use Outlook.com for my custom email accounts (and how you can too)
Microsoft’s best-kept email secret is an online tool that allows you to connect any custom domain to its shiny new Outlook.com back end, for personal or business mail. It’s free, and it works amazingly well. [Update: Microsoft has ended this service.]
A personal email address used to be something you got for free from your Internet service provider, whereas business email cost a small fortune.
With the rise of free webmail services, the personal email landscape changed, but business mailboxes have remained pricey.
Now, thanks to aggressive competition between Microsoft and Google, that situation has changed. You can get business-class email for a relative pittance. And if you don’t want to pay for a modern mail server but still want to use a custom address with your business domain, you can now get that for free.
I’ve just converted several domains that had been running on ancient POP servers to a modern, cloud-based infrastructure. And it didn’t cost a dime. You can do the same.
First, a little background.
Back at the dawn of the commercial Internet, I registered a custom domain for my personal and business use. One of the first things I did with that new domain was to attach it to a POP mail server and create a default email address.
I now own and use more than a dozen domains, but that first domain is still going strong. I’ve used that original email address for nearly two decades now. During that time I’ve lived in four states, changed Internet service providers a half-dozen times, and transferred the domain to different hosting providers without ever losing contact with my friends, co-workers, and family. I switched to a different default address for business e-mail a few years ago, but I have never stopped using that original address.
I could have chosen Google Apps for Business or Office 365, but either of those options would have meant a hefty annual bill.
As you can imagine, a 20-year-old email address, especially one with a common name to the left of the @ sign, attracts a lot of spam. Over the years, I’ve tried a bunch of spam-filtering options. None of them were close to perfect, but SpamAssassin passed the “good enough” test for a long time. A good decade, probably.
The trouble with SpamAssassin is that its technology hasn’t kept up with the bad guys, and over the past year or two the amount of junk mail that was bypassing the filters and landing in my inbox was steadily increasing.
And I’m not the only one with a mailbox on that domain. My mom has her primary account there, and my wife still receives some personal and business messages through an account there.
When the two most important women in my life both complained that the spam had gotten out of hand, I knew it was time to act.
So I decided to shut off the POP server and move that domain to a cloud-based service with its own spam filtering.
I could have chosen Google Apps for Business or Office 365, but either of those options would have meant a hefty annual bill: $50 per user for Google’s solution, $48 per user (and up) for Microsoft’s plans. (Those Google Apps accounts used to be free for up to 10 users, but Google dropped that option last year. If you set up an account before the cutoff date, you're grandfathered in, but there is no longer a free Google version for custom domains, only for Gmail.com addresses.)
But these are primarily personal accounts, so why should I pay a minimum of $150 a year? I decided instead to go with Microsoft’s best-kept secret: the free online tool that allows you to connect any domain to Outlook.com and keep email, contacts, and calendars in sync on just about any device.
Boy, am I glad I did that.
For the past three weeks, all three of those accounts, complete with custom domains, are now going through Microsoft’s mail servers. I’ve created some new accounts as well, using up 10 of the 50 addresses (and if I need more I can just put in a support ticket).
Here’s what I’ve gained:
Amazingly good spam filtering. My main account gets between 300 and 500 spam messages per day, for a total of more than 10,000 per month. I’ve been monitoring that folder obsessively for the past three weeks. Only five messages of more than 7000 that I considered spam actually made it to my inbox. Fewer than 10 legitimate messages were caught by the spam filters. All of them were bulk messages that I ended up deleting anyway.
Cloud backup. The trouble with those ancient POP servers is that they use a store-and-forward method that requires me to manage those archives somehow. Yes, I can use IMAP, but that’s still a crude technology compared to Exchange ActiveSync, which powers Outlook.com. And the same sync technology allows me to keep contacts and calendar items in the cloud as well.
Easy connections to Microsoft Outlook. I use Outlook 2013 for my work email, which is handled by an Exchange server. I can connect any Outlook.com account (including my old Hotmail addresses) to Outlook as well. This support is built in to Outlook 2013; for Outlook 2010 and 2007, you need to install the free Hotmail Connector.
Server-side rules. Microsoft calls this feature “sweep,” and it’s a very clever implementation that allows me to define flexible ways of handling different types of messages. “Just keep the most recent newsletter from Woot. Clean out daily news alerts from The New York Times after 10 days. Always move messages from the IPG mailing list to their own folder.” And so on.
There’s no such thing as a free lunch, of course. The web version of Outlook.com includes unobtrusive ads that appear to the right of the main email window. Those ads are not context-sensitive: the advertising engine does not use the contents of the current message or other messages in your mailbox to determine which ads to display, as Gmail does. Incoming and outgoing messages do not include ads. (If you use a dedicated email client program such as Outlook, you’ll see no ads at all.)
Best of all, I get to keep my custom email address. If an alternative service comes along at some point in the future and I decide to switch, I can move my custom address. I own it. You can’t do that with an address in someone else’s domain, including Outlook.com and Gmail.com.
Oddly, the back-end service that makes this feature possible still uses the old Windows Live branding. It feels very … 2007. It’s scheduled for a visual refresh and a usability makeover to fit in with the look and feel of the new Outlook.com services, although Microsoft hasn’t said when that’s going to happen. But you can use it today, without waiting for those changes.
Alas, that promised visual refresh never happened. Instead, Microsoft pulled the plug on the Custom Domains service. If you want to use a domain you own with Microsoft's servers, you'll need to sign up for an Office 365 plan, at a cost of $5 a month and up.