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3513 :: Can't send email via port 587 with TLS

• alexsad (orginal) [2018-01-29T16:12:53+01:00] view original

  How send email via port 587 with TLS?

  trying:

  import smtp, net
  
  let ctx = newContext(protVersion = protTLSv1, verifyMode = CVerifyPeer, certFile = "mycert.pem", keyFile="mycertkey.pem")
  let smtpConn = newSmtp(useSsl = false, debug=true, sslContext = ctx)
  smtpConn.connect("smtp.office365.com", Port 587)
  #smtpConn.connect("smtp.gmx.net", Port 587)
  smtpConn.auth("***", "***")
  Run

  get error: Error: unhandled exception: Expected 334 reply, got: 504 5.7.4 Unrecognized authentication type [DB6PR04CA0034.eurprd04.prod.outlook.com] [ReplyError]

  for gmx.net: Error: unhandled exception: Expected 334 reply, got: 530 Must issue a STARTTLS command first [ReplyError]

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• dom96 (orginal) [2018-01-29T16:34:04+01:00] view original

  Tried with useSsl = true?

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• alexsad (orginal) [2018-01-29T16:42:23+01:00] view original

  Yes.

  Then:

  Error: unhandled exception: error:1408F10B:SSL routines:SSL3_GET_RECORD:wrong version number [SslError]

  exception on: smtpConn.connect("smtp.office365.com", Port 587)

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• woggioni (orginal) [2018-01-29T19:44:38+01:00] view original

  @alexsad what is your OS and which SSL library are you using? It might be that you SSL library doesn't support SSLv3 which is now deprecated and unsupported on some linux distros (e.g. I'm using archlinux and here OpenSSL is compiled without SSLv2 and SSLv3 support)

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• alexsad (orginal) [2018-01-30T09:48:03+01:00] view original

  @woggioni no, here other issue if set parameter useSsl = true in newSmtp then error raise in net.nim

  when defineSsl: #in our case true!
      if socket.isSSL: #in our case true!
        # RFC3546 for SNI specifies that IP addresses are not allowed.
        if not isIpAddress(address):
          # Discard result in case OpenSSL version doesn't support SNI, or we're
          # not using TLSv1+
          discard SSL_set_tlsext_host_name(socket.sslHandle, address)
        
        let ret = SSLConnect(socket.sslHandle)
        socketError(socket, ret) #in our case here error
  Run

  sorry, I don't understand this block :)

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• woggioni (orginal) [2018-01-30T21:49:00+01:00] view original

  Anyway that error is related to the SSL protocol version the client and the server are trying to negotiate. See here for example. I think it little nothing to do with Nim SSL wrapper, you could try to connect with curl with a command like this

  
  curl --url 'smtps://smtp.office365.com:587' --ssl-reqd --mail-from '[email protected]' --mail-rcpt '[email protected]' --upload-file mail.txt --user '[email protected]:password' --insecure
  Run

  and check if you obtain a different result

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• alexsad (orginal) [2018-01-31T13:54:17+01:00] view original

  Couldn't render post #21985.

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• woggioni (orginal) [2018-02-01T08:52:10+01:00] view original

  If you see this

  
  error:1408F10B:SSL routines:SSL3_GET_RECORD:wrong version number
  Run

  STARTTLS has already happened and OpenSSL has already come into play since that message comes from 'ssl_err.c:665' in OpenSSL source code (the line number refers to version 1.1.0g). There must be some problem with Nim's usage of OpenSSL in the net module (which is where the library is called, you will not see it in smtp.nim)

  UPDATE: I think the problem is in net.nim at line 496:

  newCTX = SSL_CTX_new(SSLv23_method()) # SSlv2,3 and TLS1 support.
  Run

  I suspect that, despite the comment, SSLv23_method just supports the old SSLv2 and SSLv3 protocols which are now deprecated on many servers, it should use TLSv1_method by default. Check here for documentation

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• echo (orginal) [2018-02-05T04:34:52+01:00] view original

  When you use SSL, you need to specify this parameter when compiling:

  
  nim c -d:SSL xx.nim
  Run

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• pauline5 (orginal) [2019-12-03T07:38:24+01:00] view original

  The following forum resolved my issue. I have another query. I am getting an issue that whenever I am trying to sign in to a Microsoft cloud service such as Office 365, Microsoft Azure, or Microsoft Intune, I am receiving the following error message from ADFS that "There was a problem accessing the site. Try to browse to the site again.".I have contacted the helpdesk support and followed accordingly https://supportprop58.com/office-setup/how-to-login-microsoft-office/.Guide us if anything I have missed out.

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