Outlook Sync "Could not open a trusted connection to Outlook"

This is often caused when the Outlook was open when the Outlook Sync was installed or updated, when the Outlook Sync add-in is either removed, disabled or inactive within Outlook or If the wrong bit version was installed.

Please note: Outlook Sync bit version needs to match that of Outlook, not the Windows Operating System. To find out which bit version of Outlook you are running, within Outlook navigate to File>Office Account>About Outlook.
(x86) = 23 bit

(x64) = 64 bit.

1. Close out of Outlook and re-open it by running it in Admin mode.

2. In outlook navigate to File>Options>Add-ins

• If you are seeing the Office Tools Outlook Connect Addin as shown above, click Go…
  Please note: If our add-in is listed under the Disabled Application Add-ins you may need to change Manage: to Disabled Items then select Go...
  

  Check the box for Office Tools Outlook Connect Addin

  
  
  Please note: If the Load Behavior states anything other than the above, Outlook may be forcing our add-in out of the Active Applications Add-ins and you should contact OfficeTools by CARET Technical Support.

  
  
• If you are not seeing the Office Tools Outlook Connect Addin in the list shown above, click Go… 
   
  From this window select the Add button and navigate to this file path: 
  C:\Program Files (x86)\Office Tools\Outlook Sync
  
  Then select OutlookConnect.dll and press OK.
  
  
  Press OK on the COM Add-ins Window
  
  
  Close out of Outlook and re-open it to run in regular mode.

3. After you have enabled our add-in, or re-added our add-in re-launch the Outlook Sync and verify that it launches in your system tray