iCloud + Outlook Equals IT Headache - InformationWeek
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iCloud + Outlook Equals IT Headache

Once Outlook is connected to iCloud, iCloud begins moving things around in Outlook. This is annoying for individuals, but could be a real enterprise support headache.

When the iPhone 4S launched with iOS 5 last month, it also came with the new iCloud service that synchronizes important data like appointments and contacts with the cloud. The service also comes with an Outlook conduit. The problem is, once Outlook is connected to iCloud, iCloud begins moving things around in Outlook. This is annoying for individuals, but could be a real support headache for the corporate environment.

Once you tell iCloud to connect to Outlook, iCloud begins creating a new primary folder in Outlook called "iCloud" and a number of subfolders called Contacts, Reminders as well as Home and Work calendars. It then proceeds to move data, without asking, from your main Outlook folder.

According to Bob Lewis at InfoWorld, the only way to reverse the operation is to uninstall iCloud and then restore your PST file from a backup. You do regularly back that up, right?

The problem with this in a corporate environment is there are no PST files, at least not for live data. Outlook keeps all of your key information in an OST file that is locked to your Exchange user account. When that data is trashed, the only way to restore it is through the backups in place by the IT department. Trust me, Exchange admins don't like being called during lunch to restore a user's mailbox because an unauthorized third-party tool deleted all of their contacts.

Office Watch has a few articles on how Outlook and iCloud interoperate. Both the iCloud and Microsoft Outlook and Problems with iCloud and Outlook articles recommend you avoid using these two pieces of software together.

There will always be a struggle between users that want to bring in outside tools they are comfortable with and IT departments that would have an easier time if PC's were locked down to just a few approved apps. Apple's iCloud is another example of why users should work with the IT department and not behind its back. Not only would they find out iCloud is a bad idea, they would learn they don't need it. Exchange is a far better cloud.

Even if you have a standalone version of Outlook, you should think twice before connecting it to iCloud.

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User Rank: Apprentice
1/7/2012 | 8:28:37 AM
re: iCloud + Outlook Equals IT Headache
Microsoft needs to stop protecting their Windows business and move e-mail entirely to the server side (as all the other major ISVs, SAP, Oracle, IBM, etc, did ten years ago with their applications) for easier synchronization and integration. Microsoft isn't making an effort to integrate their stuff with Apple in order to gate Apple entrance into the enterprise.
User Rank: Apprentice
12/30/2011 | 2:27:33 PM
re: iCloud + Outlook Equals IT Headache
And by the way, how about collaboration between iCloud and Outlook.
How came that iCloud claims to be entitled to "move around things", as you say, in outlook?
How came that Outlook allows iCloud (or an other third party) to do it?
If you invite me to do some work in your kitchen, would you allow me to move around anything without asking, just because I think I now better?

It's incredible how many things we IT-Professionals impose on others.
And it has nothing to do with Microsoft or Apple or Google, this attitude is IT-ecumenical.
User Rank: Strategist
11/7/2011 | 8:43:15 PM
re: iCloud + Outlook Equals IT Headache
I agree with your encouragement that end-users should work _with_ their IT departments, rather than behind the IT department's back. A little up-front discussion can save everyone a lot of hassle and headaches.

However, I do not agree that iCloud is a bad cloud, nor that Exchange is a better one. In fact, I don't think really consider Exchange much of a cloud at all. More like a fog bank. (And I don't mean that derogatorily ... it's just closer to the end user.)

iCloud is NOT an enterprise solution. Apple doesn't claim that it is, and -- as you point out with the Exchange conduit -- it doesn't behave like one.

But it's entirely possible -- probably even likely -- that iCloud will save some user's critical document that we, in IT, didn't even know existed. And us just asking the user, "Well, have you checked your backup that happens automatically via iCloud? It should be there." could allow IT to look like more of a helpful force within a company than one that's always highly restrictive and saying "no".

And iCloud could really be a god-send for entrepreneurs and super-small shops where back-ups are seldom performed otherwise.

In the end, there are pros and cons to most things that touch IT. iCloud is no different.
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