Well after months of frustration with the same problem I've finally found a solution that has worked for me. Given the plethora of solutions I've come across I'm convinced that this issue probably has many causes & I don't expect this solution will help everyone. BTW, I'm running Outlook 2010 (64-bit) on a Windows 7 PC (64-bit); iTunes (v12.3.317 the latest at the time) & have an iPhone5S that I synchronise using a USB cable (I've never used iCloud to sync).
There were two (maybe three) issues at play for me:
- Inactive & missing add-ins in Outlook
- A "corrupted" SyncServices folder in Windows
- An old version of MobileMe Control Panel still installed on the PC
The solutions below were all from various blog & forum posts.
1. Missing add-ins in Outlook:
Inspecting the Outlook Add-Ins (open Outlook & go to: File - Options - Add-Ins) the "Outlook Change Notifier" Add-in was Inactive.
Select "COM Add-ins" in the Manage drop down-menu & click "Go..." to active this.
Missing was the "iTunes Outlook Addin".
This proved harder to resolve. I couldn't find the iTunesOutlookAddIn.dll file anywhere on my system but it did exist in an old back-up I had from over 6 months ago in the following folder:
C:\Program Files\iTunes\
Despite copying the file to this folder & being able to select it, Outlook wouldn't retain it in the Add-In list.
In desperation I tried copying it to both the following folders:
C:\Windows\System32\
C:\Windows\SysWOW64\
I thought I would see if I could select it from there in Outlook, but much to my surprise when I opened the Add-Ins page it had appeared as an Active Application Add-in (in the iTunes folder) without any intervention from myself.
I don't understand DLLs enough to explain what happened, all I can say is that it worked.
If you don't have a backed up copy of the iTunesOutlookAddIn.dll file I don't know how you go about acquiring one.
Although I now had the required Add-ins in Outlook it still didn't fix my problem.
2. A "corrupted" SyncServices folder in Windows
Following on piece of advice (which had helped many others) I renamed the sync services folder in Windows from:
C:\Users\<my account>\AppData\Roaming\Apple Computer\SyncServices
to
C:\Users\<my account>\AppData\Roaming\Apple Computer\SyncServices_OLD
When I started up iTunes next it created a new sync services folder & the option to synchronise my contacts & calendar with Outlook had returned. At last!
3. An old version of MobileMe Control Panel still installed on the PC
Finally I don't believe this issue contributed to this problem but I will include it for completeness just in case it did. I had been receiving a pop-up error message every time my PC booted into Windows 7 stating "AppleSyncNotifier has stopped working".
It may just be coincidental that this appeared around the same time I encountered the Outlook problems, but to resolve this matter I had to uninstall the long since redundant MobileMe Control Panel which still appeared in the Windows Control Panel under Programs and Features.
I'm not a guru with any of this stuff, but I'm mighty happy that I've finally found a way to fix things up. BTW, I never reinstalled iTunes or Outlook at any stage.
I hope this helps someone. Good luck!