Hello Raphi,
Seems that you have corrupt elements in CRM or Outlook that is generating C:\Program Files\Microsoft Office\Office 14\Outlook.EXE error message when trying to force synchronization.
You could verify corrupt elements in Outlook calendar to determine if you have corrupt appointments in CRM or in Outlook calendar that are blocking synchronization
1. Identify affected users
2. Verify CRM email configuration
3. Update CRM Outlook for all users to same server version
support.microsoft.com/.../3036179
4. Download Calendar Checking Tool in all machines same version as office 32 or 64 bits
www.microsoft.com/.../details.aspx
5. Unzip tool
6. Run calcheck application
7. Open CalCheckErr Excel file
8. Identify if there are corrupt items (empty file means no corrupt items)
9. Delete corrupt items in Outlook Calendar and CRM Activities if has relationship with CRM
10. Delete CalCheckErr Excel File
12. Run CalCheck application
13. Verify if file is empty, if not run process until file is clean
14. Configure CRM Server Side Synchronization and monitor behavior
15. To better troubleshooting activate warning alerts in organization until SSS configuration is stable
Removing corrupt elements will improve performance in Outlook and CRM, improve connectivity between CRM and CRM Outlook, reduce risks for Server Side Synchronization failures, reduce amount of warning and error alerts in CRM.
To detect in a better way corrupt elements in Outlook Calendar
a. Open Microsoft Outlook and click on the Calendar folder.
b. Go to the View menu and select Arrange By -> Current View -> Active Appointments to see a list of all of the active appointments for the current user.
c. Scroll through the list until you locate the damaged appointment. It should be easy to because it will be the same appointment for which Microsoft Outlook routinely displays reminders. If for some reason you don't know the name of the damaged appointment, you can try opening appointments -- damaged appointments usually won't open.
d. Once you have located the corrupt appointment, delete it.
Also verify that you have *.onmicrosoft.com, *.live.com, *.microsoft.com *.dynamics.com urls added in trusted sites if applicable, CRM Outlook uses IE to generate connection and password validation for CRM.
A recommendation is to run ccleaner to delete temp and cookies that could cause sync blocking: www.piriform.com/ccleaner
Another possible cause can be because there was a corrupt upgrade or installation and will be needed do a full uninstall to clean registers keys that are blocking synchronization.
community.dynamics.com/.../full-uninstall-of-microsoft-crm-outlook-client.aspx
social.technet.microsoft.com/.../11752.dynamics-crm-2011-outlook-client-uninstall.aspx
Hope this can be helpful for you and can solve the incident
Best Regards,