So, if you happened to notice that the OutlookSync service is missing or no longer functioning after the 2021.1 update – you may need to manually reinstall the services.

ConnectWise did release a KB article: https://docs.connectwise.com/ConnectWise_Support_Wiki/System/Calendar_sync_service_missing_on_premise_server. Unfortunately, working with support can be time consuming to fix a simple issue such as this.

You will want to open up PowerShell as administrator and run the following command:

New-Service -Name "OutlookSync" -BinaryPathName 'C:\Program Files\ConnectWise\OutlookSync\OutlookSyncService\OutlookSyncService.exe' -DisplayName "ConnectWise Outlook Sync" -StartupType Automatic -DependsOn MSMQ -Description "Synchronizes appointments between ConnectWise PSA and Exchange"

What we are doing is registering the OutlookSync.exe executable as a service, setting it to automatically startup, and adding a dependency on the MSMQ service. Once this is done, you can start the service.

Verifying/Reviewing Results

You can verify the service is functioning properly by opening the following file (as admin):

C:\Program Files\ConnectWise\OutlookSync\frontend\run.bat

You can also review the log files. They can be found here:

C:\ProgramData\ConnectWise\Outlook Sync\logs