Solving the iCloud Outlook Sync Horror

I want to start this off by thanking the folks at CodeTwo for an absolutely elegant solution to the overly complex disaster area in the making for users of Apple’s iCloud solution to sync between iDevices and Microsoft Outlook. My tale of “Fear and Loathing in Sync City” follows.

I had been using MobileMe with Outlook 2010 for over a year. While Contacts synced between MobileMe and my PST file, MobileMe created its own Calendar, necessitating a kludgy manual process of copying items between thee Calendar in my PST file and the cloud based MobileMe calendar. While you can use MobileMe on its own as your Outlook Calendar, full functionality in Outlook (Outlook Today) other integration is missing. So I religiously copied calendar items back and forth. It was a real mess accepting appointments/meetings since after copying to MobileMe from Outlook, the originator received another confusing acceptance (which was non suppressible).

Apple had been sending gloom and doom reminders about the eminent demise of MobileMe and I was dreading the move from MobileMe to iCloud for a lot of reasons, but was particularly unhappy about the addition of another set of Contacts in a Cloud based folder and losing the ability to sync Contacts with my local PST file. I couldn’t accept another set of manual work arounds to keep things in sync so I procrastinated and ignored the invitations to move to iCloud.

I was even more apprehensive after checking fellow MVP Diane Poremsky’s assessment at http://www.slipstick.com/outlook/icloud-and-outlook-problems/ Diane further documents the issues at http://www.slipstick.com/outlook/icloud-outlook-problems-syncing-calendar/ and http://www.slipstick.com/outlook/icloud-outlook-problems-syncing-contacts/ – and on the bottom of the contacts sync problem page, there was a section of tools and a link to http://www.codetwo.com/sync-for-icloud/

Diane has a stellar reputation for only highlighting tools and procedures that work, so I didn’t feel the need to research the add-in or the company behind it, CodeTwo, aggressively. Upon visiting CodeTwo’s web site, it was obvious that they were a class act with a well designed site that included great documentation, videos, descriptions, and support links.

I really wondered if I was dreaming and if a simple elegant tool could solve the potential horror of Apple’s flawed implementation. Realizing that sooner or later I would have to move from MobileMe (the devil I knew) to iCloud (the devil I didn’t yet know), I decided sooner rather than later was the best approach (hopeful that I would beat the rush at the end of June when everyone left on MobileMe would apparently be forced to migrate).

I first made several backups of my PST files and stored them in various places. Then I exported my Calendar, Contacts, Notes, etc. to individual PST files and made copies of those in various places. That might have been overkill, but it made me feel better.

Surprisingly, the actual migration from MobileMe to iCloud was relatively painless. I did hold my breath while I watched Contacts disappear from my iPad (but they reappeared rapidly when the migration was completed). Migration was uneventful on my iPhone as well. I slowly exhaled as I started up Outlook. I saw the MobileMe calendar disappear and I saw the new iCloud calendar appear. And I verified I had my original Contacts and the new iCloud based contacts.

 

I then installed CodeTwo’s iCloud Sync. Configuration was as simple as documented and I set up two way sync. I ran a couple of tests from my iPad, iPhone and from Outlook and was (and still am) amazed at how seamless this sync up is. CodeTwo has a large number of screen shots and videos on their site, and I encourage readers to take a look. The between an entry in a local PST file and iCloud is in real time.

I literally finished typing Meet Ellen for Breakfast in the local PST based Calendar when iCloud Sync copied it to the Outlook Calendar stored in iCloud. I immediately checked my iPad and iPhone and the new appointment appeared there as well. CodeTwo documents that sync between Outlook and iCloud on devices depends on connection speed, etc., but in my experience, these devices are syncing nearly in real time.

I’m impressed. And I’m happy. I’ve got two more Windows 7 OS based computers to add to the mix and I’ll wait a while longer before attacking that. For now, I’ve got my main Windows PC and iCloud sync under my control, thanks to CodeTwo’s iCloud Sync.