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Exchange 2010/Outlook 2007 send connector not delivering all emails externally

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 name@domain.com 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?

Regards,
Torrey
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Torrey Bates
Asked:
Torrey Bates
1 Solution
 
Hypercat (Deb)Commented:
There is no way to do this.  Exchange recognizes internal email addresses and won't send them through an external connector. It is "authoritative" for those addresses, so it sends them directly to the local mailbox.

You do not have to have a 3rd party SSL certificate to use Activesync.  You can use the self-signed certificate, although the users may get prompted when they set up their smartphone mail to download and install the certificate.  Most smartphones these days are capable of doing that.  Also, I don't know why they would think they can't afford an SSL certificate. You can purchase one from GoDaddy (UNC certificate, which is what Exchange 2010 needs) for around $150 for one year.
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Simon Butler (Sembee)ConsultantCommented:
You can get SSL certificates suitable for Exchange for a lot less than $150, more like $70/year. Dropping the POP3 connector completely would be the best option here, as already explained, the behaviour you are seeing is to be expected.

SBS 2011 SSL certificate installations can be tricky, I have instructions here:

http://semb.ee/sbs2011ssl

Simon.
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Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
Until they can afford an SSL cert

This is what fascinates me.  As Simon noted above, the certificate should be about $70/year or less if you use a GoDaddy promo code.

Let's assume that this organization has at least 12 users?  We're talking about $5.00 PER USER to get this done -- which is equivalent to as much time as they spend each day trying to figure out why their email on their phone is not the same as their computer.

It is costing them much, much more for you to screw around with trying to create an alternate solution!
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Torrey BatesPreidentAuthor Commented:
1st to clarify no way to do what is needed with what is in place.

1st to clarify a free self-signed SSL cert can be used with Exchange ActiveSync until a 3rd party UNC certificate can be purchased.

Side note - Affiliated with GoDaddy,  a Starfeild Technology partner priced a cert at $50 per year.
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