voicemail to email failing

[Jeffnortel]

IPO 500v2 R9.1 w/vmpro on Windows OS

Can someone help me understand what's going on with vmail to email based upon the SMTP log below?

Backstory... vmail to email stopped a while back and the assumption was that the TLS version was no longer supported from the 9.1 IPO VM pro server to Office365. So the customers Office365 environment was configured to allow SMTP from no TLS devices.

https://www.youtube.com/watch?v=xS-ci5J51JE

Seems like a viable workaround but we're still having issues.

Any thoughts or advice is appreciated!


26/10/2022 20:32:57.139 - Attempting to connect to host companyabc123-com.mail.protection.outlook.com on port 25, local bound address is (null)
26/10/2022 20:32:57.250 - Successfully connected to host companyabc123-com.mail.protection.outlook.com on port 25
26/10/2022 20:32:57.659 - < 220 BN8NAM11FT067.mail.protection.outlook.com Microsoft ESMTP MAIL Service ready at Thu, 27 Oct 2022 00:33:02 +0000
26/10/2022 20:32:57.834 - ######## START OF CHUNK ######
26/10/2022 20:32:57.995 - > EHLO voicemail
26/10/2022 20:32:58.075 - ######## END OF CHUNK ######
26/10/2022 20:32:58.165 - < 250-BN8NAM11FT067.mail.protection.outlook.com Hello [70.xx.xx.146]
26/10/2022 20:32:58.165 - 250-SIZE 157286400
26/10/2022 20:32:58.165 - 250-PIPELINING
26/10/2022 20:32:58.165 - 250-DSN
26/10/2022 20:32:58.165 - 250-ENHANCEDSTATUSCODES
26/10/2022 20:32:58.165 - 250-STARTTLS
26/10/2022 20:32:58.165 - 250-8BITMIME
26/10/2022 20:32:58.165 - 250-BINARYMIME
26/10/2022 20:32:58.165 - 250-CHUNKING
26/10/2022 20:32:58.165 - 250 SMTPUTF8
26/10/2022 20:32:58.285 - ######## START OF CHUNK ######
26/10/2022 20:32:58.393 - > STARTTLS
26/10/2022 20:32:58.559 - ######## END OF CHUNK ######
26/10/2022 20:32:58.640 - < 220 2.0.0 SMTP server ready
26/10/2022 20:32:58.740 - ######## START OF CHUNK ######
26/10/2022 20:32:58.826 - > EHLO voicemail
26/10/2022 20:32:58.938 - CSMTPConnection::SendChunk: Failed to send data chunk error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure
26/10/2022 20:32:58.990 - CSMTPConnection::ConnectESMTP: An unexpected error occurred while sending the EHLO command. error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure
26/10/2022 20:32:59.068 - ######## START OF CHUNK ######
26/10/2022 20:32:59.130 - > HELO voicemail
26/10/2022 20:32:59.179 - CSMTPConnection::SendChunk: Failed to send data chunk error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure
26/10/2022 20:32:59.267 - CSMTPConnection::ConnectSMTP: An unexpected error occurred while sending the HELO command error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure
26/10/2022 20:32:59.313 - ######## START OF CHUNK ######
26/10/2022 20:32:59.359 - > QUIT
26/10/2022 20:32:59.409 - CSMTPConnection::SendChunk: Failed to send data chunk error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure
26/10/2022 20:32:59.459 - CSMTPConnection:isconnect: Failed in call to send QUIT command error:140790E5:SSL routines:SSL23_WRITE:ssl handshake failure
26/10/2022 20:32:59.517 - <
26/10/2022 20:32:59.568 - CSMTPConnection:isconnect: An unexpected QUIT response was received
26/10/2022 20:32:59.643 - CSMTPConnection::Connect: An unexpected HELO/EHLO response was received
26/10/2022 20:32:59.709 - CSMTPConnection:isconnect: Already disconnected from SMTP server, doing nothing

 

[sizbut]

Its still failing on security. There's a mismatch between what the IP Office is using and Office365 is expecting/allowing.

Stuck in a never ending cycle of file copying.

 

[Jeffnortel]

That's what I thought but why would I see TLS and SSL references if I'm using port 25 and authentication is not required?

 

[Nortel4Ever]

In my experience smtp.office365.com requires port 587 and TLS enabled

https://learn.microsoft.com/en-us/e...-send-email-using-microsoft-365-or-office-365

 

[Z-man]

Office 365 needs port 587 and TLS, and you have to go into the control panel and allow it to use SMTP client authentication from that mailbox.