Outlook.com + Windows Phone + Windows 8 = HEAVEN

By | June 13, 2013

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Let’s face it, Windows Phone, Windows 8, and Outlook.com are purpose-built to work together. And why not – their polygamist marriage is f***ing AWESOME. If you’re using a 3rd party for your e-mail instead of Outlook.com and are as gung-ho about the rest of the Microsoft ecosystem as I am, you’re an idiot.

I was until yesterday.

A few weeks back I caught a headline in my ZDNet daily newsletter by a fellow Microsoft fan, Ed Bott. It was titled Why I use Outlook.com for my custom email accounts (and how you can too). Whoa… wait what? I can use Outlook.com w/ my OWN domain? Hells yeah! I put it on my “to read” list and finally carved out time last night to have a gander and even tackled the whole deal.

In the post, Ed explains why you should and also walks you through setting up Outlook.com to field your own e-mails from you@yourdomain.com. I love this because I use, and have used, ONE @bc3tech.net e-mail address for MANY years. If you’re reading this, you probably have done so as well.

And you know what I’m about to point out.

Using one e-mail address for a long period of time gives you 2 things:
1) People now know where/how to reach you via e-mail. They never have to wonder if you still have that address anymore
2) Spam. Lots and lots and lots of Spam.

The 2nd part of that list is what I have recently started struggling with. I HAD to find a way to trim that down, and either these bastards are getting smarter, or SpamAssassin is getting dumber. And I doubt it’s the latter. Unfortunately as I tweaked my SpamAssassin settings on my Hostgator control panel to be more strict – which did help – I started getting GOOD messages sent to the Junk folder, which started to annoy me. When Mr. Bott pointed out how one of the awesome advantages here is you get the power of MICROSOFT (a champion, btw at shutting down numerous botnets in the past few years) filtering your spam, I knew I had to at least give it a try.

So I walked thru Ed’s post and got everything set up. As I closed in on the final moments of testing it out, I found one primary catch that I couldn’t overlook.

You can’t set up an e-mail forwarder to another address in your Custom Domain handling.

For me this was a deal breaker. For each of my Windows Phone apps, I set up an e-mail address to use in the app for people to send me support/feedback/hate mail. That e-mail address is set up in my Hostgator CP to forward right on to my personal mail. It doesn’t have its own box, no login, nada. Just a straight up dummy account that drops it somewhere else. The benefits of this are 1) users don’t get my personal address and 2) I can still filter based on the “To” line of the e-mail and drop it in a special folder w/in my own mailbox.

If I wanted to do this on my new Custom Domain in Outlook.com, I would have to:
1) Create a mailbox for each forwarder
2) Log in to each mailbox, go to Settings, set up mail forwarding
3) Make sure I log in once every 365 days or the account “looks inactive and could be deleted”

Screw that. Not only would it end up being horribly tedious, but it also – in effect – creates a whole Microsoft Account for that *dummy* e-mail address (from what I could tell). That annoyed me.

So what to do? It’s worth noting that the answer is to not go through w/ what Ed proposed (set up a Custom Domain handler w/ Outlook.com), but rather a slight modification using the beauty of Outlook.com “aliases”:

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When Outlook.com first launched, I was sure to nab the @outlook.com address I wanted. I simply added this as an alias to my Microsoft Account on Outlook.com

See where I’m going?

I never used the @outlook.com address. Until now.

Notice that in my Aliases setup, I have a bc3tech.net account as my primary alias – this will be key later on, so if you aren’t set up like this, get there by going to your Outlook.com settings:

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It’s also there that you can ramp up an @outlook.com address of your own as an alias – which you’ll want/need for this to all work.

Keep in mind that all the steps I’m about to do are only necessary because I’m a lazy bastard and don’t want to chew up Microsoft Accounts and spend my time logging in to about 40 different forwarders once a year. I don’t have >50, but if I did that would also be another forcer as you can only have 50 e-mail addresses in your Microsoft Outlook Custom Domain before you have to manually request (and maybe pay) for more. Since each forwarder would in effect be an e-mail account, they’d count against your quota.

Before we get too far, let me describe how my current mail is handled.

Hostgator fields my mail. It runs it through a list of forwarders first – if one’s found it follows the trail. In some instances I have multi-chain set up (one goes to another and then finally goes to me) to break down redundancies.
After it finally gets to my account, it goes through an account filter ruleset that I have set up. In this rule set are things like “if ‘to’ contains ‘bizsaver’ move to ‘app support\bizsaver’” and such.

And now, the disclaimer: Doing this will not keep the e-mail in your current mailbox. In fact you can’t (or I couldn’t figure out how to) move it to Outlook.com. It is only effective from now going forward.

For this reason I did the following to backup my current mailbox:
1) Create an IMAP (or POP3 if you want) account in Microsoft Outlook (proper, not metro) that goes at my current e-mail server/setup. If you choose POP3, elect to download all messages and you’re done.
2) [IMAP] Elect to keep all mail offline
3) Create new data file (pst) w/in Outlook
4) Copy all folders from IMAP acct –> new data file

You now have a PST file in Outlook that represents all your “before I got smart” e-mail.

Now back to business.

I thought to myself “hmm… what would happen if I put a forwarder on my actual e-mail address, that one that has the actual mailbox I log in to check?” and in true Brandon fashion, I just did it. I created a new forwarder for me@bc3tech.net and pointed it to me@outlook.com.

Bam. E-mail showed up in Outlook.com. What’s more, since me@bc3tech.net is set as my Primary Alias on Outlook.com, when I sent mail it showed as coming from me@bc3tech.net, not me@outlook.com – exactly what I wanted. This setting can be tweaked on Outlook.com in the same area as your

But there was one glitch.

When I sent mail to bizsaver@bc3tech.net, it didn’t come to me@outlook.com. The rules I had set up in Hostgator were nabbing it, moving it to the folder w/in IMAP, and stopping all further processing. Dammit.

I played around w/ various configurations and layers of indirection here for a good hour before I finally arrived at the solution that works (for me). If the rules are running and intercepting the message, but I don’t want to delete the rules in case this all doesn’t work. Just create a new (first) rule that stops all further rules. GENIUS!

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All mail that comes to me@bc3tech.net is now forwarded to me@outlook.com without fail. Keep in mind that this involved no MX record or other DNS modification. It’s basically just another “forwarder” that picks up my bc3tech.net mail and sends it on over to Outlook.com where I can read it. On top of doing this, I also shut off the spam filtering on Hostgator so I am now fully using Outlook.com’s. For good measure, I also put in an E-mail Forwarder on me@bc3tech.net that sends stuff over to me@outlook.com. From what I can tell this is the one that gets hit first, then if something is sent from another forwarder to me@bc3tech.net, the user-level rule shown above picks that up and sends it to Outlook. So far it’s working perfectly.

The added bonus here is that you get this integration now on your Windows Phone. Y’know that Microsoft Account you set up when you first got it? The one where you unchecked the box next to ‘Email’ under ‘Content to sync’?
Go turn that back on

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And look you now get push mail (as items arrive)!

That IMAP account you still have on your phone, desktop, tablet? Still works. You can leave that hanging around to access your “before I got smart” e-mail because it’s still a mailbox in the same old spot on the same old server – all its incoming mail’s just getting intercepted and sent over to Outlook.com now.

The same goes for the Microsoft Account you set up in Windows 8 and unchecked the ‘Email’ option for:

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Now you’re fully tied in to your Microsoft Account in all its glory. No more dependencies on IMAP/POP.

The added beauty for me with this setup is that I could now get my personal e-mail inside Microsoft Outlook. My company blocks IMAP/POP outgoing connections, but not Exchange ActiveSync. Since that’s what Outlook.com uses, boom.

Here is how you set up Microsoft Outlook (2013) with your Outlook.com account (when using it in this manner):

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Note the password here is the password to your Microsoft Account, not the one to your mail server (that is still sitting there w/ your IMAP access)

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Notice how it automatically knew to use Exchange ActiveSync to hit the m.hotmail.com server.

And you’re done. You’ll now get not only Mail, but Calendar information right in Microsoft Outlook, integrated w/ your other devices using that Microsoft Account as well.

Hope this helps you, like me, see the light and enjoy the beauty of Outlook.com’s interface and its power in helping you with your e-mail by filtering spam and giving you other sweet tools like automatic newletter deletion & unsubscribing and mailbox cleanup. It’s also worth noting that the same rules I talked about setting up at Hostgator which would sort my bizsaver@bc3tech.net mails to special folders are able to be set up within Outlook.com to do the same kinds of things!