Outlook automation failing to send e-mails via Exchange.

I'm not sure if this is the correct place to post this but here goes:
We  have an application written in VB6 which automatically generates e-mails in Outlook . The customer in question was using use Outlook 2010 with Exchange 2003 they have recently migrated
to Exchange 2013. Since migrating all generated e-mails have stopped being sent out and are all being bounced back with:
Remote Server returned '550 5.1.0 RESOLVER.ADR.InvalidInSmtp; encapsulated INVALID address inside an SMTP address (IMCEAINVALID-)' 
When I go into Outlook to try to resolve the issue and drive down into the properties of the recipient of the e-mail the e-mail type field is blank (see screen shot below) where as before the migration the e-mail type always defaulted to SMTP. I'm
not sure if this is what is causing the issue but its the only difference i can see post migration.
I have looked at the Outlook object model and cannot see where I can set the E-Mail Type property. Can anybody advise my how i can programatically set the E-Mail Type property to SMTP
Thanks in advance
Chris

How are those systems configured to send through your Exchange server? Are they configured to send as an authenticated user, or is it basically anonymous?
If they're not configured to send as a valid user then your scenario makes sense. When sending to an external address via the server you're effectively asking it to relay the email. Exchange will naturally block any relay attempts from unknown sources, otherwise
anyone could send spam via your server. When sending to a distribution list the destination is local to Exchange, therefore relaying isn't required and the message is allowed.
I imagine if you receive the failure reports when you try sending to
[email protected] that the report will be something along the lines of "550 relay denied".
I suspect your best option will be to setup a user in Exchange for the purpose, and then configure those apps to authenticate to Exchange using that login, but that obviously depends on the capabilities of those apps and how they connect to your server.

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