From: DeskNow Knowledge Base
http://www.desknow.com/kb/

The automated sync does not work in Outlook 2007
http://www.desknow.com/kb/idx/17/202/article/

If you're using the SyncML Outlook connector with Outlook 2007 and Windows Vista or Windows 7, the 'Auto Sync' option does not seem to work if Outlook is running (it works when Outlook is not open)

This is caused by increased security checks done By Outlook and Windows. To solve this issue, make sure to open Outlook as Administrator (shift-click on the Outlook icon in the Start menu, and select 'Run as admnistrator').