Exchange 2010/Outlook 2007 send connector not delivering all emails externally
Posted on 2014-02-24
I have a client with Exchange 2010 on a SBS 2011 box and Outlook 2007 on all workstations.
Here is the setup:
1. Mail is delivered to the mail hosting company and sits on that Server (web.com).
2. Using program POPCON to retrieve emails every 3 minutes to the Exchange Server 2010 which is on a SBS 2011 box at the office. POPCON leaves the messages on the mail hosting company Server for 1 day because of #4.
3. People use Outlook 2007 at the office to send and receive email.
4. People have iPhones or Droids to also retrieve their email using a POP account direct from mail hosting company's Server.
Until they can afford an SSL cert and that setup so they can use Exchange Sync they are fine with this setup to get emails onto smartphones and realize no contacts or calendar will sync.
HERE IS THE ISSUE:
When they send emails from Outlook 2007 to fellow employees, not selecting them from the Global Address book, actually typing in firstname.lastname@example.org and send it's like they skip the Exchange Send Connector like all other emails do. It appears they get delivered directly to their Exchange mailbox and never leave the building. Problem is these emails don't make it to the mail hosting company's Server and the employees cannot get those emails on smartphones.
To try and work around this for now I setup a pop account in Outlook 2007 as the send from this account by default but that only fixes the issues on new emails. I found out during testing that replies and forwards in Outlook 2007 just picks which email account it feels is best to send on and it keeps picking Exchange. The Outlook 2010 and 2013 registry hack to force account to send from does not work on Outlook 2007.
How can I get Exchange to use the setup Send Connector for employee to employee emails locally?