I am thinking that because Voicemail Pro has been attempting TLS all these years and that lower versions were acceptable it might be the issue. What baffles me is that they say this however the IP Office itself does not have TLS checked/enabled and is sending email notifications absolutely fine. 12:07:20.275 - CSMTPConnection::Disconnect: Already disconnected from SMTP server, doing nothing RE: Voicemail Pro V9.0.3 cannot send voicemail-to-email TLS/SSL issue? derfloh (TechnicalUser) 1 May 19 18:52ĪACon - would you happen to know where Voicemail Pro TLS modifications are made? (To enforce a specific version) The IT team advised that TLS 1.2 was enforced last Friday within their Exchange environment so at least I now have proof that something had changed. 12:07:20.172 - CSMTPConnection::Connect: An unexpected HELO/EHLO response was received 12:07:20.070 - CSMTPConnection::Disconnect: An unexpected QUIT response was received 12:07:19.965 - CSMTPConnection::Disconnect: Failed in call to send QUIT command error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure 12:07:19.754 - CSMTPConnection::ConnectSMTP: An unexpected error occurred while sending the HELO command error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure 12:07:19.544 - CSMTPConnection::ConnectESMTP: An unexpected error occurred while sending the EHLO command error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure 12:07:18.694 - Successfully connected to host on port 587 12:07:18.591 - Attempting to connect to host on port 587, local bound address is (null) Here is a copy of the repeated SMTP Logs from Voicemail Pro which gets generated on every email attempt: Any insight or ideas would be greatly appreciated! I also tried to find information on disabling STARTTLS in an effort to test (which even though is not optimal I just want to know if this is the cause). Would anyone have an insight on what might have gone wrong? I am not sure what TLS version is supported on 9.0.3. Originally we were on port 25 but modified to be 587 still with no luck. If I use Putty and telnet to mail server and issue a STARTTLS command it fails as well. I think this is where things go down hill. Looking through these logs I see that Voicemail Pro (once it establishes a connection to the mail server and after the EHLO command) issues the "STARTTLS" command. The phone system (V2 on same version) is sending alarms/notifications without issues so I focused completely on VM Pro. Last Friday things took a turn and can no longer send voicemail to email. We regularly use Voicemail-to-Email for a majority of users. I have a client Voicemail Pro system (yes still running on Server 2008 R2) that has been running for past 2 years on 9.0.3.
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