AutoEntry Sync normally runs as a windows service, which is outside the scope of user interactive mode in Windows.
If the connection to Sage hangs, Sage may be trying to display a pop-up window, which is not possible when running as a Windows Service.
1.) Stop the AutoEntry Sync service and verify all processes exit
2.) Navigate to C:\Program Files (x86)\OCRex\AutoEntry\Service and then run the file ( AutoEntry.DesktopSync.Service.exe ) Leave the command prompt screen open and go to next step.
3.) Navigate to C:\Program Files (x86)\OCRex\AutoEntry\Client and run AutoEntry.DesktopSync.Client.exe by double clicking it, this runs the service in User Interactive Mode, under the current user's account.
Test connecting to Sage 50 again through the AutoEntry sync app, additional error messages may appear if they were being blocked when AutoEntry Sync was running as a Service.