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TIP: Mavericks won't sync Outlook & iPhone, but Exchange is a workaround

By John Rizzo

Readers are reporting that since updating to OS X 10.9 Mavericks, their iOS devices no longer sync calendars or contacts with Microsoft Outlook via iTunes. Workarounds are few because the problem is the result of Apple removing Sync Services from Mavericks. Sync Services was the core OS X software that enabled syncing of devices and Mac apps through iTunes.

Mavericks no longer supports direct Mac-to-device syncing. Instead, Mavericks only syncs with iOS devices through servers that use software protocols called CalDAV (for calendars) and CardDAV (for contacts) protocols. These servers include OS X Server and cloud-based services such as iCloud, Google Calendar and Yahoo Calendar. Unfortunately, Outlook for Mac does not support CalDAV or CardDAV, and can't sync through these services.

There is a workaround from Microsoft. Both Mavericks and iOS 7 (and earlier) still support syncing through Exchange Server. This will work with either Exchange installed on your network or with Microsoft Exchange Online. The latter is not free, but is only $4 per month for a single-user subscription.

(Sycning iPhones and iPads with Exchange isn't always trouble free, but Mavericks doesn't seem to have added any new problems with iOS 7.)

There is speculation that Microsoft will update Outlook for Mac to support CalDAV and CardDAV. Considering that these protocols are open standards that first appeared in Macs in 2005 with OS X 10.5 Leopard, it's not likely we'll see adoption of CalDAV and CardDAV from Redmond anytime soon.

There is one more (though more complicated) workaround: run Outlook for Windows on your Mac in a Windows virtual machine using Parallels Desktop, VMware Fusion, or Oracle VirtualBox. Although Apple hs removed Sync services from OS X, it continues to offer Sync Services for Windows, including Windows 8. Sync Services is included in the current version of iTunes for Windows, so you can do direct iOS-to-Windows syncing. Admittedly, installing Windows in a virtualization environment just to direct-sync iPhone to Outlook is a lot of expense in terms of dollars and Mac resources. But if you're already running Outlook for Windows in a virtual machine, this is an easy solution.