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Question:

Sending Email via office365.com

Jun 14 '15 at 15:26

I get the following error when trying to send email using outlook.office365.com: With old Version MAILMAN2 I dont'have problem... Thanks

ChilkatLog:
  SendEmail:
    DllDate: Dec  8 2014
    ChilkatVersion: 9.5.0.46
    UnlockPrefix: LINEASMAILQ
    Username: CS_LABS:Stefano
    Architecture: Little Endian; 32-bit
    Language: ActiveX
    VerboseLogging: 0
    recipients:
      TO: email@domain.com
      totalCount: 1
    --recipients
    renderToMime:
      createEmailForSending:
        xSigningAlg: sha1
        Auto-generating Message-ID
      --createEmailForSending
      renderToMime: Elapsed time: 0 millisec
    --renderToMime
    progressTotal: 566
    smtpConnect:
      SmtpHost: smtp.office365.com
      SmtpPort: 587
      SmtpUsername: loginname@domain.com
      SmtpSsl: 0
      StartTLS: 1
      SmtpConnect:
        Need new SMTP connection
        checkForExistingConnection: Elapsed time: 0 millisec
        Connecting to SMTP server smtp.office365.com:587
        smtp_host: smtp.office365.com
        smtp_port: 587
        smtp_user: mail@domain.com
        socketOptions:
          SO_SNDBUF: 65536
          SO_RCVBUF: 65536
          TCP_NODELAY: 1
        --socketOptions
        socketConnect: Elapsed time: 109 millisec
        SmtpCmdResp: 220 AM3PR01CA023.outlook.office365.com Microsoft ESMTP MAIL Service ready at Sun, 14 Jun 2015 10:04:49 +0000
        initialResponse: Elapsed time: 31 millisec
        ehloCommand: EHLO CS_LABS
        Will be using STARTTLS...
        sendCmdToSmtp:
          SmtpCmdSent: EHLO CS_LABS<crlf>
        --sendCmdToSmtp
        SmtpCmdResp: 250-AM3PR01CA023.outlook.office365.com Hello [79.0.45.38]
        SmtpCmdResp: 250-SIZE 157286400
        SmtpCmdResp: 250-PIPELINING
        SmtpCmdResp: 250-DSN
        SmtpCmdResp: 250-ENHANCEDSTATUSCODES
        SmtpCmdResp: 250-STARTTLS
        SmtpCmdResp: 250-8BITMIME
        SmtpCmdResp: 250-BINARYMIME
        SmtpCmdResp: 250 CHUNKING
        ehloResponse: 250-AM3PR01CA023.outlook.office365.com Hello [79.0.45.38]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
250-BINARYMIME
250 CHUNKING
        sendCmdToSmtp:
          SmtpCmdSent: STARTTLS<crlf>
        --sendCmdToSmtp
        expectCommandResponseString:
          SmtpCmdResp: 220 2.0.0 SMTP server ready
        --expectCommandResponseString
        clientHandshake:
          clientHandshake2:
            readHandshakeMessages:
              processHandshakeRecord:
                processHandshakeMessage:
                  processServerHello:
                    serverHelloExtensionsLen: 9
                    HelloExtension: status_request
                    HelloExtensionLen: 0
                    HelloExtension: renegotiation_info
                    HelloExtensionLen: 1
                  --processServerHello
                --processHandshakeMessage
                processHandshakeMessage:
                  processCertificateRequest:
                    tooShortLoc: 3
                    CertificateRequest message too short
                    totalLen: 4
                    msgLen: 6
                  --processCertificateRequest
                --processHandshakeMessage
              --processHandshakeRecord
            --readHandshakeMessages
          --clientHandshake2
        --clientHandshake
        Client handshake failed. (1)
        connectionClosed: 0
        Failed to establish TLS connection.
      --SmtpConnect
      checkOrMakeSmtpConnection: Elapsed time: 265 millisec
    --smtpConnect
    Failed.
  --SendEmail
--ChilkatLog

Accepted Answer