Has anyone looked at the Exchange server log yet? That should show the authentication failure as well. I don't know if that will give you more information as I've never looked at an Exchange server log myself but the files you included don't provide any info on why authentication failed. Does your Exchange server require SSL? If so that's your problem as your E-mail Engine mailbox setting is No.
To test that you could try doing a telnet from your E-mail Engine server to port 25 of the Exchange server and try to log in that way to see if that gives you any extra info. I saw a few articles about your "530 5.7.1 Client was not authenticated" error and they pointed to a property not set correctly on the Exchange side. They were regarding anonymous access but there still might be something on the Exchange side that needs to be corrected. Example article: http://krypted.com/windows-server/resolve-530-5-7-1-client-was-not-authenticated-error-in-exchange-2010-2012/ Apparently there can be multiple Client Connectors configured in Exchange so checking the Exchange log might show that your session is hitting a different connector than the Exchange admin expected it to hit. -Rick -----Original Message----- From: Action Request System discussion list(ARSList) [mailto:arslist@ARSLIST.ORG] On Behalf Of Hennigan, Sandra, CTR, DSS Sent: Wednesday, October 29, 2014 10:45 AM To: arslist@ARSLIST.ORG Subject: Outgoing Email New install of 8.1.01. - Working to configure Outgoing SMTP The Config, std.err.log & stdout.log are attached. We are fighting "530 5.7.1 Client was not authenticated" error in the stderr.log - Outgoing email messages error out and are not sent. NOTE: The mailbox information was not entered during the installation as the mailbox was just created this week. The Exchange Admin made sure that the ARS server was in the SMTP relay & that the user information was correct. The AR System does not require authentication. The TCP port is correct. Port 25 is open for use. The password has been retyped. We have switched between using the User name or the Email address as the Email Server User. The AR Email service was restarted between changes. Any assistance is appreciated. Thank you, Sandra Sandra Hennigan _______________________________________________________________________________ UNSUBSCRIBE or access ARSlist Archives at www.arslist.org "Where the Answers Are, and have been for 20 years" _______________________________________________________________________________ UNSUBSCRIBE or access ARSlist Archives at www.arslist.org "Where the Answers Are, and have been for 20 years"