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Failed to send via smtp from Hesk RRS feed

  • Question

  • Hi everyone, I have a problem when I configure the sending of mail by a PHP application installed on IIS, it should use TLS authentication via SMTP to send mail externally to the network where the Exchange server is present.

    Currently, SMTP forwarding works only within the domain of the Exchange 2010 server (On windows server 2008 r2), setting the application on port 25 and without authentication.

    The reception of emails also works from the outside, on port 993, with the ssl protocol.

    The application is Hesk (an open source ticket system), installed on IIS on a Windows Server 2016 server in the same Exchange domain.

    The error I get when configuring TLS and authentication is as follows:

    Resolving SMTP server domain "mail.****.**"...
    Connecting to SMTP server "mail.****.**" port 587...
    Connected to SMTP server "mail.****.**".
    S 220 SRV****.****.** Microsoft ESMTP MAIL Service ready at Fri, 10 Apr 2020 08:53:56 +0200
    C EHLO srv****
    S 250-SRV****.****.** Hello [192.168.10.36]
    S 250-SIZE 10485760
    S 250-PIPELINING
    S 250-DSN
    S 250-ENHANCEDSTATUSCODES
    S 250-STARTTLS
    S 250-AUTH NTLM
    S 250-8BITMIME
    S 250-BINARYMIME
    S 250 CHUNKING
    C STARTTLS
    S 220 2.0.0 SMTP server ready
    Starting TLS cryptograpic protocol

    Can someone help me ? Could I have to configure in connector?

    Monday, April 13, 2020 4:20 PM

All replies

  • please provide the following information:

    • what certificates do you use for the smpt service on the exchagne side? (self signed or from a public CA, valid - also with matching names etc.)
    • do you can increase the log level of your receive connector you have configured to be used for your help desk application -> you should then be able to see the logs in the transport smtp receive directory.
    • your copy + paste of SMTP connection does not include any error - as your last step is starting tls -> and  this could be because of untrusted certificate, untrusted (no matching) ciphers to be used etc.

    Please remember to mark the replies as answers if they helped.

    Monday, April 13, 2020 4:47 PM