I have long had my main address book in the cloud on what is now called Outlook.com’s People app. It not only is my central store of all contact information, it is also smart because it is connected to twitter, LinkedIn, Facebook and Google. As a result, my “master” contact card for any person is smart enough to show me not only what I have for them in my address book but also information that they have chosen to make available to me via any and all of those networks.

So, the central store and federation is a big deal. Coupled with those things, I am able to pull in this address book via Exchange Active Sync (read: 2-way, instantaneous push and sync) on all my devices: Windows Phone, Windows 8, iPhone, iPad, Android.

Needless to say, this has become indispensable for me. I love that I am able to forget about syncing and keeping a master record, and more importantly, not worry about losing that data if I lose or reset a device.

However, the downside is that when something weird happens, it instantly becomes a major cause for worry for me. Like a few weeks ago, my niece’s contact information disappeared from my iPhone. The way I realized it was through WhatsApp; her message showed up without a name and instead, just a nick and a phone number. I looked up my Contacts on the iPhone and couldn’t find her. I panicked. I had no idea what happened. Was I hacked? Was there something I did? What could delete this account? What else was deleted? All these thoughts started circling in my head. The problem of complete automation, I guess.

The good news was that the contact existed on People app on the web, and it also existed on my Windows devices. The phone number though, was missing. Bizarre. I added the number because I wanted to first get back on track and then troubleshoot. For whatever reason, I could not force a sync back to the iPhone. It is supposed to be instantaneous, but it simply did not bring that contact over to the phone! I contacted Microsoft support on twitter and posted on their forums.

Anyway, since it was so random, Microsoft support suggested I just remove and re-add the account on iPhone and see if that resolved the issue and it did. Problem solved, kinda-sorta. It was “solved” for the support team. Not for me. However, I had no idea what may be going on, and no time to investigate. So I ended the chapter there, with slight dissatisfaction of knowing I had not really solved the problem, only worked around it.

Today, I noticed that another family member’s phone number is missing from my phone’s contacts. Again, it showed up because in WhatsApp, her message showed just the nick and the number. I checked the phone, and the contact does not exist, and in this case, the contact as well as the phone number exists on the web as well as Windows devices.

Something really strange is going on with the way contacts are syncing from Outlook.com to iPhone via the “Outlook” account type (not “Exchange”). I am not sure if it is something Outlook.com needs to address or Apple, but I know that I am just not comfortable with the setup I have at the moment.

Time to create some backup plans. :-(

As you may or may not be aware, my personal email (with “vanity” domain) is hosted on Office 365. Yes, that business service which charges $6/month for Exchange, SharePoint and Lync Online. I have had it since they launched the small business and professionals plan.

Since then, Hotmail has gone from being the dull and boring email service no one wants to be associated with, to a beautiful and modern Outlook.com. While Hotmail always provided the ability to use custom domains, I never thought of using that option because it was not a great email service. For example, there was no easy way to connect to it from a desktop email client unless you use Outlook Express or Windows Live Mail. Outlook added a Hotmail Connector but it always felt like a hack. And of course, there’s mobile.

With Outlook.com, what’s nice is that it supports Exchange Active Sync out of the box. No connectors needed. No jumping through hoops. 2-way sync, push support and all that jazz. For free. I have been tempted to move my domain email to this combination except that my mailbox is fairly huge (5GB) and I was not sure if I will be able to move the entire thing and I was not even sure how long it would take.

So I did some quick experiments with my existing Hotmail account and realized that via IMAP, I am able to move my emails fairly quickly over Comcast’s speedy internet connection (and maybe a much better back-end on Outlook.com?). So, I decided to take the plunge and make the move.

I disconnected my email account from my domain on Office 365, “removed” the domain from Office 365’s management, added the same to Live Domains and set up my account there. With some small glitches here and there (my email was an alias on my existing Hotmail account, so I wasn’t able to add it as a new domain email account until I removed the alias), I was up and running with my new setup.

I used Outlook 2013 to connect to my Office 365 account (via normal “Exchange” connectivity) and Outlook.com account (via IMAP). I started moving emails by folders and realized most of the messages were showing up on the web fairly quickly. Except for two very large folders, I was done in a couple of hours. The large folders took a bit longer but not terribly so. Overnight, I was actually surprised that I was done with the email part. What remained was calendar and contacts, both of which created much pain.

I took it for granted that calendar can be moved as easily as email but I was in for an unpleasant surprise when I realized I was connected to Outlook.com via IMAP. That means, no calendar support. I saved the Office 365 calendar as an ics file (was not under “export” but under “save as” in Outlook 2013 - go figure) and imported it from the web. That was easy, except that the “save as ics” step did not save every single event! There was no obvious pattern in what was saved and what was omitted.

Another idea struck me: why not connect to Outlook.com via EAS in Outlook 2013 and then copy all calendar events from one account to the other? Great idea, except there is a massive bug in Outlook 2013’s EAS implementation which does not sync events if you mass-copy them on a calendar. If I did all 350-odd events one-by-one, it would have worked. But I was not in a mood to do that. So the workaround was to simulate an edit across all the events and that is easily achieved with marking them all as a new category. That seemed to trigger a forced sync and I started seeing the events show up on the web. What seemed to be missing was events that I had marked as private, or at least some of those private events. Again, the EAS bug comes to bite me because even after marking them all as normal sensitivity, I could not simulate a sync. At this point I kinda gave up on the sync and re-saved the calendar as ics and imported it from the web. Then, a sync happened that showed up in Outlook 2013. For all the stuff that was not correctly sync-ed, including some recurring events that ended up showing as one-time, I manually went to the web and added/updated. :-(

As for contacts, I moved to Outlook.com as my “single source of truth” for contacts long time ago. I have been pretty happy with the arrangement especially because most of the contact manipulation (adding/updating/deleting) happens on mobile devices and with EAS, I am seconds away from always being up-to-date. Additionally, I have linked my Microsoft account to LinkedIn, Facebook and Twitter and as a result, I have the “master” address book under People on my Outlook.com account. However, there is no way for me to link that account with the new account I created. No sharing, no linking, no sync-ing, and that’s a pity. I was hoping that just like I link a Facebook, Twitter or LinkedIn account with Microsoft account, I could another Microsoft account too. Not to be. So I went for the next best option, which was to export and import. I could export my Outlook.com contacts as a csv but shockingly, when I tried to import, I got a generic error that seemed to indicate that there are some special characters in some phone or email fields somewhere in that csv file. No partial import, no specific error on specific records, nothing. An all or nothing which to me ended up with nothing. In the end, I had to go back to Outlook 2013 and with EAS, I was able to copy contacts from one account to the other.

Despite those multiple hiccups, I am glad to say I am done with the migration much sooner than I thought I would be and most importantly, there were no issues with the email migration. I was afraid of duplicates and missed emails neither of which happened.

I will monitor for a few days after which I am going to cancel my Office 365 paid account but a practical limitation I am facing now is that at work where I prefer to keep personal email limited to a tab in a browser, I won’t be able to see my current Hotmail account and the new custom domain account in a single browser window. With Office 365 account, I was able to because they don’t share the cookie, I suppose, but with both the accounts now running off Outlook.com back-end, I am unable to. It is a pain to have two browser windows open, one of which is an InPrivate window, but I am sure it is something I can get used to over time.

And to finish off, can I just say that Microsoft has made a big mistake calling their webmail service Outlook.com which is very close to their email client Outlook. Searching for solutions to the various problems I had almost invariably landed me on help pages for Outlook the program vs Outlook.com the service. It was quite frustrating. :-(