Author Topic: Handshake failed with exchange mail server with port 465 SSL enabled.  (Read 196 times)

mdilshad

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Can someone please help me with this.

ChilkatLog:

  SendEmail:

    DllDate: Aug  3 2011

    UnlockPrefix: SOCEANPTMAILQ

    Username: DILSHAD02:SYSTEM

    Architecture: Little Endian; 64-bit

    Language: .NET 4.0 / x64

    recipients:

      TO: manojk2@idc13.commvault.com

      totalCount: 1

    renderToMime:

      createEmailForSending:

        xSigningAlg: sha1

        createFromMimeText5:

          createFromMimeObject2:

            security:

              FromHeader: "Dilshad 02" <dilshad02@commvault.com>

              ToHeader: manojk2@idc13.commvault.com

      renderToMime: Elapsed time: 0 millisec

    SmtpConnect:

      SmtpHost: 172.16.60.100

      SmtpPort: 465

      SmtpUsername: Administrator@idc13.commvault.com

      SmtpSsl: 1

      StartTLS: 0

      Need new SMTP connection

      SMTP_Connect:

        Connecting to SMTP server 172.16.60.100:465

        smtp_host: 172.16.60.100

        smtp_port: 465

        smtp_user: Administrator@idc13.commvault.com

        ConnectTimeoutMs: 30000

        calling ConnectSocket2

        This is an IPV4 numeric address...

        AddrInfoList:

          AddrInfo:

            ai_flags: 4

            ai_family: 2

            ai_socktype: 1

            ai_protocol: 0

            ai_addrlen: 16

            ai_canonname: (NULL)

        Connect using IPV4.

        ipAddress1: 172.16.60.100

        myIP_3: 172.16.62.216

        myPort_3: 57079

        connect successful.

        clientHelloMajorMinorVersion: 3.1

        buildClientHello:

          majorVersion: 3

          minorVersion: 1

          numRandomBytes: 32

          sessionIdSize: 0

          numCipherSuites: 10

          numCompressionMethods: 1

        Timeout waiting to read socket or accept connection

        timeoutMs: 30000

        Failed to read TLS record (2)

        tlsRec_msg: 0

        msgLen: 8269

        Expected ServerHello but did not receive it.

        Client handshake failed.

        Failed to connect to SMTP server.

      checkOrMakeSmtpConnection: Elapsed time: 30016 millisec

    Failed.

Chilkat

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Re: Handshake failed with exchange mail server with port 465 SSL enabled.
« Reply #1 on: January 12, 2018, 12:48:43 PM »
You're using a very old version of Chilkat from 2011.  Update to the latest to see if the problem is already resolved.

In general, protocols such as TLS, SSH, etc. will evolve over the years to newer protocol versions, newer algorithms, etc.  Servers will begin disallowing what was previously secure in past years, but is no longer secure.  It is not a valid expectation that software (never updated), will continue to work when interacting with servers that are updated from time to time.  The current version of Chilkat (or anything else) in 2018 will surely not work with whatever exists in 2028, which hasn't yet been invented.

My recommendation is to avoid being too many years out-of-date.  If you are using something quite old, such as in this case, it is overwhelmingly likely that updating to the latest version will fix the problem.