Why I use Outlook.com for my custom email accounts (and how you can too)

Why I use Outlook.com for my custom email accounts (and how you can too)

Summary: 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.]


[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 "Microsoft ends support for custom domains in free email 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.

Topics: Networking, Microsoft

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  • Only 50 addresses?

    Too bad they don't allow catch-all addresses.
    • .

      haven't MS ditched catch all email addresses even in exchange 2010 and upwards?
      • ...

        Not sure. I've primarily used webmail providers for the past 8+ years. ;)
    • Outlook.com is a total fail

      Many things are very disturbing and if they don't change it (I doubt they will change it) I never gonna switch.

      1. No catch-all (solution is to create a full mail account for each alias and forward it to the main account, totally absurd, also one has to login to each mail alias account every x days)

      2. Skydrive is censored. I am not allowed to upload as a backup for myself (no sharing!) the beach photo of my wife. The TOS forbid it and many users have been locked out because of such thing.

      3. No IMAP. I know probably only 1% need IMAP. I need it.

      4. No custom display images for address book contacts.

      5. Indian Microsoft support with copy and paste answers in their forums

      6. Spam filter is as bad as the Gmail spam filter.
      • Nope it is not

        @JamesDevon, I didn't agree with you, especially on #3I am using my outlook on my Andriod and Windows Phone, using Exchange, so though techincally Imap is not there, but I can still use it like IMAP.

        #5 that is true for all Tech support of any company, so why you include that in outlook failure only ?

        #6 Outlook has better spam protection as I feel, though both Gmail and mS are all good.
        • I'll agree and add to it

          2. I don't know what specific issue you're having, but I haven't been rejected for any file ever on Sky Drive. Even if it's in TOS, why would a photo of you're wife on the beach be "censored"?

          3. Exchange active sync is effectively IMAP on steroids. It functions the same, is much more reliable, and works on ALL my devices. IMAP is antiquated so IMO "doesn't have IMAP" in this case is a good thing.
    • Just one email address fill up fast, i could not imagine 50 email addresses

      Just one email address fill up fast, i could not imagine 50 email addresses
  • Google already has this.

    Mr. Bott, I am not sure if you know this, but free-Gmail already has this feature. As a matter of fact, I have been using it for years. As for their anti-Spam feature, not only has THAT been around for years, but it's also considered to be Legendary and superior to other free and non-free email solutions.
    • I already use my own domain with Gmail

      How do I create multiple accounts for family members with one free Gmail address?

      By the way, the real problem with Gmail spam filtering is that it puts a lot of legitimate email in the spam box. The last two times I've looked,. my Gmail spambox has been 100% legitimate email, and it's often 30-50%. Outlook.com lets a little spam through but it never (so far) puts legitimate email in the spambox.

      Whether this makes Gmail "better" is another question, but it's one reason I shifted my wife's account from Gmail to Outlook.com: she's much more reliable at deleting spam than she is at retrieving Gmail mistakes from the spambox.
      Jack Schofield
      • Outlook.com false positive

        While I've had an Outlook.com account for a while now, I only started actively using it recently. The first e-mail that appeared in my Junk folder at Outlook.com was a legitimate e-mail (an account activation e-mail from a service I had signed up for).
      • Gmail spambox

        The only legitimate email I see in my Gmail spam is email from companies that I consistently delete without reading. For instance, I've bought clothes for my wife from a couple of online stores. I don't want to read their email specials unless it's close to anniversary, Christmas or birthday, so they get deleted a lot. After awhile, I will see that stuff start showing up in Spam. This is part of "training" Gmail to recognize spam.
        big red one
        • I temporarily used Gmail for journal purposes...

          While moving my mail archiving from a local box to a cloud provider. Gmail randomly moved messages from my users into spam. I created specific rules and wildcard rules for every user / domain in my organization and still kept finding hundreds of messages in there every week.

          Also, automatically deleting the messages once they had been archived via my archiving application didn't work because Gmail doesn't actually delete anything when you click delete. I Would have to log into the account and manually delete all the messages every day. Sometimes it would crash / freeze if I had over say 5 GB of messages to delete at once, so I would have to go through and select / delete them 100 at a time.

          TLDR; I now hate Gmail.
      • Been using Outlook much as Ed has.

        I see about one peice of spam per month in the inbox. Absolutly great I would say. No good email has gone to the junk folder yet!

        I also have a business account that my company uses through Gmail as also brought up. I also have a personal Gmail account. Personally I just like the Outlook better.

        To each his own I guess.
      • gmail spam filters work for me

        gmail spam filters work extremely well for me. Not much spam gets through and very few legitimate emails get filtered as spam. I have a custom domain hosted by gmail and, like Ed, I've had that same email address for about 20 years so I get a lot of spam.
    • Gmail is no more free

      $50 per account per year.

      Old domains which were free continue to get their pre-claimed quota.
    • You're grandfathered in

      Google stopped offering this feature as a free offering last year. Costs $50 per user now.
      Ed Bott
      • Incorrect and misleading!

        I still use it and enable such configurations for my colleagues and family. These have been set up in such a way, no one can tell from which email address or which device one responds... For example, if you have received a mail on your POP server that can't be accessed through WAN, when you respond using gmail from whichever device form whatever place, it goes as a response from your POP account without the hint from where it has been sent. I simply disagree with the evidence at hand. I don't say that now Outlook.com does not have these features.... they may very well have it, but to suggest that this is the first and is charged, It is incorrect and misleading. I have mentioned everything that has been possible for me to do with the free individual account.
        • You're just forwarding email

          You can do that with any account, but then your mail goes through two servers before it gets to you. The advantage of this type of setup, just as with Office 365, Exchange, or Google Apps for Business, is that your account is a full-fledged mailbox on the back end.

          If all you want to do is aggregate stuff from POP servers you can do that with Gmail, Outlook.com, or anything you want. But it's not the same thing at all.
          Ed Bott
    • Google SPam Filter

      I guess Google might have good Spam Filters because they are responsible for about 90% of the SPAM on the Internet already. It's sickening to look at all the companies that Google owns that are SPAM related.
    • Are you talking about the same thing?

      Be certain you aren't confusing the ability for G-Mail to fetch e-mail from your other accounts and send replies in that account's name as what this article is discussing.

      Could you set up sending and receiving e-mail from "mail@mydomain.com" without having another server somewhere receiving e-mail for that account? If not, it is not the same as what is being discussed here.

      Fortunately, I am grandfathered in to my free Google Apps account, but it is nice to have this information for clients and friends.