Email sent from Outlook with CRM for Outlook client installed, shows as Received/Incoming when using Server Side Sync in Microsoft Dynamics CRM 2013
Server Side Synchronization processes all folders of the users email and promotes them as received emails (directioncode of incoming). This includes tracked items sent from Outlook that reside in the Sent folder on Exchange. This has been identified as product limitation in Microsoft Dynamics CRM 2013.
There are a few options to work around this issue.
1. Use the CRM for Outlook Client or Email Router for the Incoming and Outgoing email access type for these users
1. Set the OrgDbOrgSettings SendEmailSynchronously setting to 1 and restart the Outlook clients. This setting forces the email promotion to occur at the time the email is sent. For more information on changing this value, see the link below:
This is being reviewed to be changed in a future release of Microsoft Dynamics CRM