In our tests, we have seen no issues syncing between Outlook for Mac 2011 and the Apple Contact and Calendar apps in Apple's latest OS releases, OS X 10.7.5 (Lion) and OS X 10.8.2 (Mountain Lion). NOTE: Microsoft has published a support article with the following information: "With OS X Mountain Lion, Apple no longer maintains active support for Sync Services. You can also set up two-way sync between Outlook for Mac 2011 and these apps to keep DejaOffice and Outlook 2011 in sync. CompanionLink for Mac synchronizes your Mac's Contacts/Address Book and Calendar/iCal apps with DejaOffice.
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