I'm having an issue sending email via SMTP AUTH on an Exchange server 2013, was hoping someone can give me some ideas on where else to check. I've had this working on other Exchange servers without any issues, but haven't been able to work out what's different with this particular server.
The MAIL FROM address I'm using is the default reply to address of the user that I'm authenticating as.
I've tried a few different accounts on this server, they all have the same issue.
The Exchange server is a fairly standard install single server with all roles.
On the Client Front End Receive connector, I've disabled 'Offer basic authentication only after starting TLS' so that I can test via telnet. Otherwise I have 'Basic Authentication', 'Integrate Windows Authentication' and 'Exchange Users' selected.
When I attempt to send an email via Telnet, I am able to Authenticate Successfully, but get a '550 5.7.1 Client does not have permissions to send as this sender'
EHLO
250-exchange Hello []
250-SIZE 36700160
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH NTLM LOGIN
250-8BITMIME
250-BINARYMIME
250 CHUNKING
AUTH LOGIN
334 VXNlcm5hbWU6
dXNlcm5hbWU=
334 UGFzc3dvcmQ6
cGFzc3dvcmQ=
235 2.7.0 Authentication successful
MAIL FROM:<username@mydomain.com>
250 2.1.0 Sender OK
RCPT TO:<recipient@somewhereelse.com>
250 2.1.5 Recipient OK
DATA
354 Start mail input; end with <CRLF>.<CRLF>
SUBJECT: Test Email
Hello
.
550 5.7.1 Client does not have permissions to send as this sender
On the exchange server with the issue, it lists 'AUTH NTLM LOGIN', it still accepts the 'AUTH LOGIN' command though - whereas another Exchange server that I am testing with that works correctly, lists 'AUTH LOGIN'
