Why I use Outlook.com for my custom email accounts (and how you can too)
[Effective April 10, 2014, Microsoft ended the Custom Domains service described here. Existing customers can continue to use addresses that are already set up, but you can no longer attach your own domain to Outlook.com. For details, see
A personal email address was something you got for free from your ISP, while business email cost a small fortune.
With the rise of free webmail services, the personal email landscape has changed, but business mailboxes have remained expensive.
Now, thanks to the aggressive competition between Microsoft and Google, this situation has changed. You can get business class emails for a pittance. And if you don’t want to pay for a modern mail server but still want to use a custom address with your work domain, now you can get it for free.
I just converted several domains that were running on old POP servers to a modern cloud-based infrastructure. And it didn’t cost a dime. You can do the same.
First of all, a little history.
With 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 this new domain was attach it to a POP mail server and create a default email address.
I now own and use over a dozen domains, but that first domain is still going strong. I have been using this original email address for almost two decades now. During that time, I have lived in four states, changed ISPs half a dozen times, and moved the domain to different hosting providers without ever losing touch with my friends, colleagues, and family. I changed my default address to work email a few years ago, but I never stopped using that original address.
I could have chosen Google Apps for Business or Office 365, but either of those options would have resulted in 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 have tried a bunch of spam filtering options. None of them were near perfect, but SpamAssassin passed the test “fairly well” for a long time. A good decade, probably.
The problem with SpamAssassin is that its technology hasn’t kept up with the bad guys, and over the past couple of years the amount of spam bypassing filters and landing in my inbox has been steadily increasing.
And I’m not the only one who has a mailbox on this domain. My mom has her main account there and my wife always receives 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 down the POP server and move this domain to a cloud based service with its own spam filtering.
I could have chosen Google Apps for Business Where Office 365, but either of those options would have resulted in a hefty annual bill: $ 50 per user for Google’s solution, $ 48 per user (and more) for Microsoft’s plans. (These Google Apps accounts were free for up to 10 users, but Google
. If you create an account before the deadline, you are grandfathered, but there is no longer a free version of Google for custom domains, only for Gmail.com addresses.)
But these are mostly personal accounts, so why should I pay a minimum of $ 150 per year? Instead, I decided to go with Microsoft’s best-kept secret: the free online tool that lets you connect any domain to Outlook.com and sync emails, contacts, and calendars. on just about any device.
Man, I’m glad I did this.
Over the past three weeks, all three of these accounts, along with custom domains, now go through Microsoft’s mail servers. I also created new accounts, using 10 of the 50 addresses (and if I need more I can just create a support ticket).
Here is what I won:
- Incredibly good spam filtering. My main account receives between 300 and 500 spam messages per day, for a total of over 10,000 per month. I have been obsessively monitoring this file for three weeks. Only five messages over 7,000 that I considered spam arrived in my inbox. Less than 10 legitimate messages were intercepted by spam filters. All of them were bulk posts which I ended up deleting anyway.
- Cloud backup. The problem with these old POP servers is that they use a storage and transfer method that requires me to manage these archives in some way. Yes, I can use IMAP, but it’s still rudimentary compared to Exchange ActiveSync, which powers Outlook.com. And the same sync technology also allows me to keep contacts and calendar items in the cloud.
- Easy connections to Microsoft Outlook. I use Outlook 2013 for my business email, which is managed by an Exchange server. I can also connect any Outlook.com account (including my old Hotmail addresses) to Outlook. This support is built into Outlook 2013; for Outlook 2010 and 2007 you need to install the free software Hotmail connector.
- Server side rules. Microsoft calls this feature “sweep” and it’s a very smart implementation that allows me to define flexible ways to handle different types of messages. “Just keep the most recent Woot newsletter. Clean up daily news alerts from The New York Times after 10 days. Always move messages from the IPG mailing list to their own folder. Etc.
There is no free lunch, of course. The web version of Outlook.com includes discreet advertisements that appear to the right of the main email window. These announcements are not Contextual: The ad engine doesn’t use the content of the current message or other messages in your mailbox to determine which ads to show, like Gmail does. Incoming and outgoing messages do not include advertisements. (If you’re using a dedicated email client program like Outlook, you won’t see any ads.)
Better yet, I keep my personalized email address. If an alternative service presents itself at some point in the future and I decide to change, I can move my personalized address. It belongs to me. You cannot do this with an address in someone else’s domain, including Outlook.com and Gmail.com.
Oddly enough, the back-end service that makes this feature possible still uses the old Windows Live brand. This is very… 2007. There is a visual refresh and usability redesign to accommodate the look of the new Outlook.com services, although Microsoft has not said when that will happen. But you can use it today, without waiting for these changes.
Sadly, that promised visual refresh never happened. Instead, Microsoft
. If you want to use a domain you own with Microsoft’s servers, you’ll need to sign up for an Office 365 plan, costing $ 5 per month and up.
[Update, April 10, 2014. Microsoft has ended this service. Existing customers can continue to use addresses that are already set up, but you can no longer attach your own domain to Outlook.com. For details, see
I have removed the instructions that were previously on this page because they are no longer functional.