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SMPT fails to authenticate as per the log below. What could the problem be

SendEmail: DllDate: Jan 19 2012 UnlockPrefix: cccc Username: TC6:username Architecture: Little Endian; 32-bit Language: .NET 4.0 recipients: TO: emailaddr totalCount: 1 --recipients renderToMime: createEmailForSending: xSigningAlg: sha1 Auto-generating Message-ID --createEmailForSending renderToMime: Elapsed time: 0 millisec --renderToMime SmtpConnect: SmtpSsl: 0 StartTLS: 0 Need new SMTP connection checkForExistingConnection: Elapsed time: 0 millisec SMTP_Connect: Connecting to SMTP server ConnectTimeoutMs_1: 50000 calling ConnectSocket2 IPV6 enabled connect with NO heartbeat. 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) --AddrInfo --AddrInfoList Connect using IPV4. ipAddress1: 251 myIP_3: myPort_3: 50746 connect successful (2) socketConnect: Elapsed time: 16 millisec InitialResponse: 220 mail..co.za ESMTP

    initialResponse: Elapsed time: 62 millisec
    sendingHello: EHLO TC6

    sendEhlo: Elapsed time: 0 millisec
    helloResponse: 250-.co.za Hi pc-00024..co.za []

250-PIPELINING 250-8BITMIME 250-SIZE 15000000 250 STARTTLS

    helloResponse: Elapsed time: 0 millisec
    This SMTP server did not list authentication methods.
    Defaulting to LOGIN authentication method.
    login_method: LOGIN
    500 Unrecognized command
    Failed to send AUTH LOGIN
    220 mail..co.za ESMTP

EHLO TC6 250-.co.za Hi pc-00024..co.za [] 250-PIPELINING 250-8BITMIME 250-SIZE 15000000 250 STARTTLS AUTH LOGIN 500 Unrecognized command

    Failed to login using LOGIN method
  checkOrMakeSmtpConnection: Elapsed time: 78 millisec

--SendEmail --ChilkatLog

asked Feb 07 '14 at 05:12

Mike's gravatar image


It appears that your SMTP server doesn't support the basic LOGIN method (nor does it report what methods it supports).

Try changing the SmtpAuthMethod property to "NONE", "PLAIN", "CRAM-MD5", or "NTLM" to see which one ultimately works. If you need NTLM authentication, then you may also need to set the SmtpLoginDomain property.


answered Feb 10 '14 at 20:52

jpbro's gravatar image

jpbro ♦

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Asked: Feb 07 '14 at 05:12

Seen: 1,738 times

Last updated: Feb 10 '14 at 20:52

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