Outlook.Com–Just Say No

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I was one of those that was irritated that Google (and the NSA) were snooping through my email and sending me ads based on the fact I was sending mail about camera lenses. But then again, I didn’t use the Gmail email client so I didn’t see the ads; I use Office’s Outlook—I always have and I’ve grown to trust it and understand it. I still do.

About 10 days ago, I forgot my basic mantra “If it’s working don’t fix it.” I was lured in by promises of… well, to quote Microsoft Outlook.Com’s own blog:

    • A fast, modern UI that shows you more of your email with less clutter
    • An address book that connects to Facebook, Twitter and LinkedIn, so all your contacts are in one place
    • Pictures from Facebook in messages from your friends, messaging that lets you chat with your friends on Facebook right from your Inbox
    • Great tools to help handle newsletters, deals and more
    • SkyDrive and Office built-in to make it easy to share and collaborate

It sounded appealing. And I was actually thinking, wouldn’t it be nice to have my Office Outlook contacts and calendars sync with Facebook and my iPhone and my laptop without having to use gSyncit (a third-party sync tool). Admittedly, I didn’t think that through. My Facebook friends are not the same as my business and personal contacts. And I was thinking the all-Microsoft solution one with Office Outlook on one end and Outlook.com on the other would better integrate with my Windows 8 OS. Perhaps I would give up my iPhone for a Windows 8 phone. Yea, pretty thin reasoning in hindsight. But I assumed that Microsoft would not lead me astray. I was wrong.

Converting my Custom Domain

So, since I have my own domain and email address, I was lead to a site that walked me through the process of setting up my MX and TXT records to point to the Outlook.com mail host and validating the configuration so Outlook.com ‘trusted’ my site. Totally understandable and while the process was a bit clunky, Peter Blackburn and I got it done in an hour or so. Too bad my site wasn’t really trusted.

Consider that Google also provides these custom MX and TXT records but also provides an easy to use step-by-step wizard to set them up. I’ve used it before and as we’ll see, I used it again just recently. Fortunately, I had been using the free version of Google’s custom domain service for years so when they started to charge for it, I was grandfathered in. To the rest of the world, creating a custom domain with Google means a $50/year fee.

This conversion went fairly smoothly, despite having to figure out some of the finer details as to priority and timeouts myself (with the help of Peter Blackburn, my IT guru). The one important fact that the blog post left off, there is no way to get your mail out of your Gmail account into Outlook.com but I’m getting ahead of myself.

Getting Connected

So in Office Outlook 2013 (OO13) I was not able to connect as many of the blogs described because I did NOT need the Office Outlook Connector. This (apparently) has been removed and replaced with a version of ActiveSync (EAS). This means that the server name you provide must be m.hotmail.com and not m.outlook.com. And that’s just the beginning. All-in-all many of the blogs are outdated and don’t apply to Office 2013 where a lot of things have changed.

Once connected with OO13, I discovered that three new calendars were born:

  • Birthdays
  • US Holidays
  • INETA (a speaker’s bureau I once belonged to)

Swell. Now my calendar (and my iPhone) were filled with birthdays for people I barely know and a litany of religious and national holidays. BUT my own calendar entries were nowhere to be found. Nothing I tried could get my OO13 calendar entries to sync with the Outlook.com calendar. I did notice that items added to the Outlook.com calendar appeared in OO13 (eventually) and on my iPhone which I had connected to Outlook.com without issue but not those items changed/added in OO13. They remained on my laptop.

I eventually (more blogs) found that if I changed the category of all of the OO13 calendar entries they would sync. This took hours to complete. So now I have my appointments in sync. But OO13 did not let me delete the birthdays or holidays—they were read-only. I eventually found that I had to do that in Outlook.com browser app. The disconnect here is that the “support” people on the forums did not know anything about Office Outlook (any version) or if they did, they didn’t know anything about Outlook.com (or so it seemed). 

I also discovered that (some of) these calendars can be removed in the Outlook.com interface but not in Office Outlook (any version)—but not all of them.

No Way to Import Mail From Custom Domains

Since I have a LOT of mail and archived historical data stored on Gmail, I needed to get that all imported into Outlook.com. The blogs said there were custom apps like TrueSwitch. Too bad it doesn’t work for custom domains like mine. My host “Betav.com” was not on the ‘recognized’ domains list despite being recognized by the MX and TXT records by Outlook.com and the world-wide DNS providers.

I was also lead to a number of blog posts that said you could simply drag your messages (in Office Outlook) from one folder to another. All you need to do is setup accounts for both the Outlook.com and Gmail hosts in Office Outlook and start dragging. Okay, I have about 45,000 messages in about 70 folders (about 1.3GB of mail) and I actually tried this (I thought I had 3 days to waste). Sadly, it didn’t work—at least not completely (okay, almost not at all). As far as I can tell, Office Outlook and/or Outlook.com got overwhelmed and while it might recreate the folders, it does not always copy the mail. And if the folders have any special characters like parenthesis, the process fails with an irrelevant (generic) error message. And it ONLY works if you are using an Office 2010 or 2007 that has the old (but functional) Hotmail Connector.

So I spent 3 days painstakingly copying folders from one account to another using an old Office 2010 system. Yes, some of the Gmail folders survived the trip so I had to go back and check one-by-one against the Outlook.com folders (using the IE interface) and repeat the process over and over again until they were all there. Thank the stars that I had backed up my Gmail account (Gmail backup) and was able to restore it totally as I accidentally “moved” instead of “copied” some of the folders.

Now that my mail was (mostly) in Outlook.com on my old Office 2010 laptop, I went over to my OO13 system. Was all of my mail there? Ah, no. Only a portion of the folders were synced—lots of empty folders. Swell. Again, no amount of pleading or syncing or slamming the system in the side with a board would get it to sync. I even left it running overnight. Yes, more folders seem to be populated, but it was like being on the end of a tight-string-and-two-cans broadband connection. At every step Outlook.com was painfully slow. My broadband connection? 25mb/25mb and the system is a i7 980x.

I started hunting around for another third-party solutions to import mail and found a few—none of them support Outlook.com. Roadblock.

Support? Ah, No.

At this point I started looking for help from Microsoft. I went to the MSDN developer blogs and was sent packing. Yea, I agree, it wasn’t a “development” issue. I was sent to Answers.Microsoft.com and bounced from one forum to another, but got mostly canned responses that didn’t help. I finally had someone ask for a private session, I sent some screenshots and my account details and apparently he “fixed” something. After that I noticed that at least 50 messages where missing and I was no longer able to connect to my account from OO13. I waited for 24 hours before giving up.

Junk Mail?

Some of the proponents of Outlook.com mention the ‘stellar’ junk mail handling in Outlook.com when compared to Gmail. I’ve worked with Gmail for a decade and I get about 2 false positives and 2 false negatives a month from messages that slip through Gmail’s spam/junk filters. I had about the same result in the week I tried Outlook.com. However in Outlook.com, there was no way to create a permanent filter to make sure that messages from specific clients were not thrown into the Junk mail folder.

What Really Works

So let’s go through the list of features that were promised and the reality of what was delivered.

  • A fast, modern UI that shows you more of your email with less clutter.

I agree that the Outlook.com is less cluttered. It’s less cluttered with necessary features. For example, in Gmail I can easily manage filters to move mail to folders based on content or sender’s email address. There are a several cool options for the filters as in “Never send to SPAM” or “skip the Inbox”—these were missing in the Outlook.com filters. And guess what? Even when a message was filtered to a folder, it still triggered the “New Mail” event. I did like Outlook.com’s list of folders but since I have about 70 of them, it’s pretty clunky when you have that many. I also didn’t like the fact that the OO13 rules were not kept in sync with the Outlook.com ‘rules’. Gmail also has a host of other options from the ability to customize the UI to managing visibly of folders (labels), to being able to assign an email message to more than one folder.

  • An address book that connects to Facebook, Twitter and LinkedIn, so all your contacts are in one place

This would be cool if it actually worked. As it is, my business calendars and contacts were contaminated with my acquaintances and friends in Facebook and LinkedIn. Synchronization of calendars and contacts only started to work when I reactivated my gSyncit application. 

  • Pictures from Facebook in messages from your friends, messaging that lets you chat with your friends on Facebook right from your Inbox

Ah, I’ve heard any number of reports of being unable to attach files of to email and how the cloud censors pictures someone thinks are offensive. I didn’t try any of this. I didn’t get that far.

  • Great tools to help handle newsletters, deals and more

I have no idea what this means.

  • SkyDrive and Office built-in to make it easy to share and collaborate

I have SkyDrive and Cloud (Apple) and Google’s Cloud Drive already. How is this an Outlook.com feature?

None of the Outlook.com features mean anything at all if the product is unreliable. I need mail to be up 99.999% of the time. In the one week that I used Outlook.com, it was down several times with “intermittent” failures and down completely for the last 36  hours—right up to the time I pulled the switch and changed back to Gmail.

In Summary

My advice to those who are thinking about Outlook.com as an alternative to Gmail? Think long and hard before doing so. You may hate Google for snooping in your mail, but what’s more important? Getting your mail quickly and making sure its available 7/24/365 or having another ad pop up trying to sell you a camera lens that you might really want in the first place? And no, I’m no longer considering the Windows 8 phone.

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This page contains a single entry by William Vaughn published on June 28, 2013 12:40 PM.

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