We're using IIS 6.0 SMTP Virtual Server to receive and forward e-mails from our website hosted on the same dedicated machine. Everything worked fine, up until we recently transfered the e-mail service to Online.net (that also hosts our dedicated web server)
on a Cloud based service. I updated the Smart Host in IIS SMTP server to smtp.cloud.online.net, as well as the Authentication credentials (e-mail + password). Problem is messages sent from our website arrive to the mail server as they used to but got stuck
in the Queue folder.
The Logs do not mention any particular error, but strange enough they never go further, to the Authentication process. Here is an exemple:
When switching back to the former Smart Host SMTP server and Authentication credentials, the messages are sent just fine. Here is an exemple of the Logs from a proper transaction:
217.76.129.126, OutboundConnectionResponse, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 63, 0, 41, 0, 0, -, -, 220 smtp-02.serveursdns.net ESMTP Postfix,
217.76.129.126, OutboundConnectionCommand, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 63, 0, 4, 0, 0, EHLO, -, MUSIQUE,
217.76.129.126, OutboundConnectionResponse, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 94, 0, 31, 0, 0, -, -, 250-flse665-a15.serveursdns.net,
217.76.129.126, OutboundConnectionCommand, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 94, 0, 8, 0, 0, STARTTLS, -, -,
217.76.129.126, OutboundConnectionResponse, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 141, 0, 28, 0, 0, -, -, 220 2.0.0 Ready to start TLS,
217.76.129.126, OutboundConnectionCommand, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 219, 0, 4, 0, 0, EHLO, -, MUSIQUE,
217.76.129.126, OutboundConnectionResponse, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 266, 0, 31, 0, 0, -, -, 250-flse665-a15.serveursdns.net,
217.76.129.126, OutboundConnectionCommand, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 266, 0, 4, 0, 0, AUTH, -, -,
217.76.129.126, OutboundConnectionResponse, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 297, 0, 16, 0, 0, -, -, 334 UGFzc3dvcmQ6,
217.76.129.126, OutboundConnectionResponse, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 344, 0, 35, 0, 0, -, -, 235 2.7.0 Authentication successful,
217.76.129.126, OutboundConnectionCommand, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 344, 0, 4, 0, 0, MAIL, -, FROM: SIZE=3211,
217.76.129.126, OutboundConnectionResponse, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 375, 0, 12, 0, 0, -, -, 250 2.1.0 Ok,
217.76.129.126, OutboundConnectionCommand, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 375, 0, 4, 0, 0, RCPT, -, TO:,
217.76.129.126, OutboundConnectionResponse, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 422, 0, 12, 0, 0, -, -, 250 2.1.5 Ok,
217.76.129.126, OutboundConnectionCommand, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 422, 0, 4, 0, 0, DATA, -, -,
217.76.129.126, OutboundConnectionResponse, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 468, 0, 35, 0, 0, -, -, 354 End data with .,
217.76.129.126, OutboundConnectionResponse, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 531, 0, 34, 0, 0, -, -, 250 2.0.0 Ok: queued as 1FA3620CD4,
217.76.129.126, OutboundConnectionCommand, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 531, 0, 4, 0, 0, QUIT, -, -,
217.76.129.126, OutboundConnectionResponse, 31/10/2017, 11:51:11, SMTPSVC1, MUSIQUE, -, 562, 0, 13, 0, 0, -, -, 221 2.0.0 Bye,
Does anyone have a clue why the new SMTP server smtp.cloud.online.net do not ask for (or would not accept) authentication from our IIS SMTP server? Everything works fine when using this same server and credentials on Outlook.