My family shares information in Mac-land, but I have Outlook inflicted on me at work. This weekend we moved from MobileMe to iCloud. Upgraded both Macs to Lion, all 3 iPhones to iOS5, and migrated the MobileMe data to iClould. In general everything was very smooth with the exception of Calendar syncing under Outlook. I have installed the iCloud Control Panel on my Windows 7 machine and enabled Calendar syncing. At first the calendar shows up just fine, but later in the day I noticed it was not tracking changes that were being made on my Mac or Phone. I searched the web and found no mention of this issue. Late yesterday, I: - closed Outlook - went to the iCloud Control Panel and disabled Calendar syncing - restarted Outlook - closed Outlook - restarted Calendar syncing from iCloud Control Panel - restarted Outlook At that point syncing worked PERFECTLY! I could add a meeting in Outlook and it showed up in less than a minute on my Mac and Phone. I could then delete from either device and within a minute, my Outlook calendar showed the change. I was happy. This morning when I booted up a work, the calendar was there, but when I modified it to add a meeting it, once again, did not show up on my Phone. I went through the above procedure of disabling and re-enabling and it once again is syncing very promptly. There has to be a better way. Has anyone had the syncing survive multiple reboots of the Windows machine? I'm going to reboot again and see if syncing continues. I'll post later on success or failure.