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. :-(