I'm not sure if this falls under a Sharepoint or Exchange issue but our environment is Sharepoint 2010 and Exchange 2003 SP2. We would like to send email directly from our Sharepoint portal but it currently cannot make it past the outbound smtp queue in Exchange.
In sharepoint Central Administration Outgoing E-Mail Settings we have the following configured.
Outbound SMTP Server - Using IP or DNS name for the Exchange server produces the same unsuccessful result.
From address - the smtp email address we are using.
Reply-to-address - the smtp address we are using.
Character Set - 65001 (Unicode UTF-8)
When an email from sharepoing is initiated it is received into our exchange smtp queue but it puts a very odd string on the email before the actual adress. If I right click on the email in the queue on the message properties this is what it lists as the sender.
It only stays in the queue for a couple minutes before it disappears but then comes back on a retry status and repeats that process over and over until I do a delete no ndr on it.
The acutal email address if firstname.lastname@example.org does not exist in our AD as according to sharepoint administraion documentation it does not need to but is set to forward to an external email adress outside our domain. We have no issues emailing to that address directly from inside our organization and even if we setup an address that does actually exist in AD to email from within sharepoint it produces the same result.