enviar e-mail via SMTP Oauth2 do Gmail

Eu posso autenticar para SMTP, seguindoo exemplo do google.

Mas o problema agora é que não posso enviar o e-mail. Estou recebendo o seguinte erro sempre que tento enviar e-mails.

com.sun.mail.smtp.SMTPSendFailedException: 530-5.5.1 Authentication Required. Learn more at
530 5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 f5sm19578172pav.22

    at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2114)
    at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1618)
    at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1119)
    at javax.mail.Transport.send0(Transport.java:195)
    at javax.mail.Transport.send(Transport.java:124)

Primeiro eu estou recebendo não pode se conectar ao host local, assim eu adicionei algumas linhas de código para propery de sessão como abaixo para OAuth2Authenticator classe, ainda authenicated com sucesso. Mas não pode enviar o email.

props.put("mail.smtp.host", "smtp.gmail.com");
props.put("mail.smtp.port", "587");

Estou usando omesmo objeto de sessão e objeto de transporte SMTP que será retornado da classe OAuth2Authenticator quando eu tiver autenticado com sucesso pela primeira vez.

            Message message = new MimeMessage(session);


        message.setFrom(new InternetAddress(msg.getFrom()));
        message.setRecipients(Message.RecipientType.TO,
            InternetAddress.parse(msg.getTo()));
        message.setSubject(msg.getSubject());
        message.setText(msg.getBody());

        transport.send(message);

Registro de Depuração Completo

DEBUG: setDebug: JavaMail version 1.4.5
DEBUG SMTP: enable SASL
DEBUG SMTP: useEhlo true, useAuth false
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 587, isSSL false
220 mx.google.com ESMTP gj1sm1027169pbc.11 - gsmtp
DEBUG SMTP: connected to host "smtp.gmail.com", port: 587

EHLO E6410-PC
250-mx.google.com at your service, [202.xxx.xxx.xxx]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250 ENHANCEDSTATUSCODES
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
STARTTLS
220 2.0.0 Ready to start TLS
EHLO E6410-PC
250-mx.google.com at your service, [202.xxx.xxx.xxx]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH XOAUTH2
250 ENHANCEDSTATUSCODES
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN XOAUTH XOAUTH2"
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Authenticate with SASL
DEBUG SMTP: SASL mechanisms allowed: XOAUTH2
DEBUG SMTP: SASL AUTH command trace suppressed
DEBUG SMTP SASL: Mechanisms: XOAUTH2
DEBUG SMTP SASL: SASL client XOAUTH2
DEBUG SMTP SASL: callback length: 1
DEBUG SMTP SASL: callback 0: javax.security.auth.callback.NameCallback@100ab23
DEBUG SMTP SASL: no response
Successfully authenticated to SMTP.
NOOP
250 2.0.0 OK gj1sm1027169pbc.11 - gsmtp
Is SMTP still connected: true
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]
DEBUG SMTP: enable SASL
DEBUG SMTP: useEhlo true, useAuth false
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 587, isSSL false
220 mx.google.com ESMTP az8sm1466819pab.3 - gsmtp
DEBUG SMTP: connected to host "smtp.gmail.com", port: 587

EHLO E6410-PC
250-mx.google.com at your service, [202.xxx.xxx.xxx]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250 ENHANCEDSTATUSCODES
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
STARTTLS
220 2.0.0 Ready to start TLS
EHLO E6410-PC
250-mx.google.com at your service, [202.xxx.xxx.xxx]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH XOAUTH2
250 ENHANCEDSTATUSCODES
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN XOAUTH XOAUTH2"
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: use8bit false
MAIL FROM:<[email protected]>
530-5.5.1 Authentication Required. Learn more at
530 5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 az8sm1466819pab.3 - gsmtp
DEBUG SMTP: got response code 530, with response: 530-5.5.1 Authentication Required. Learn more at
530 5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 az8sm1466819pab.3 - gsmtp

RSET
250 2.1.5 Flushed az8sm1466819pab.3 - gsmtp
DEBUG SMTP: MessagingException while sending
com.sun.mail.smtp.SMTPSendFailedException: 530-5.5.1 Authentication Required. Learn more at
530 5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 az8sm1466819pab.3 - gsmtp

    at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2114)
    at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1618)
    at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1119)
    at javax.mail.Transport.send0(Transport.java:195)

Editado: agora eu chamei o comando AUTH explicitamente assim.

 byte[] response = String.format("user=%s\1auth=Bearer %s\1\1",
                    emailAddress, accessToken.getToken()).getBytes();
            response = BASE64EncoderStream.encode(response);
            System.out.println("token check : " + new String(response));

            transport.issueCommand("AUTH XOAUTH2 " + new String(response), 235);

mas a resposta continua a mesma.

DEBUG: setDebug: JavaMail version 1.4.5
DEBUG SMTP: enable SASL
DEBUG SMTP: useEhlo true, useAuth false
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 587, isSSL false
220 mx.google.com ESMTP kl3sm6965596pbc.15 - gsmtp
DEBUG SMTP: connected to host "smtp.gmail.com", port: 587

EHLO E6410-PC
250-mx.google.com at your service, [xxx.xxx.xxx.xxx]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250 ENHANCEDSTATUSCODES
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
STARTTLS
220 2.0.0 Ready to start TLS
EHLO E6410-PC
250-mx.google.com at your service, [xxx.xxx.xxx.xxx]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH XOAUTH2
250 ENHANCEDSTATUSCODES
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN XOAUTH XOAUTH2"
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
Successfully authenticated to SMTP.
token check : abcdefgFuYUBnbWFpbC5jb20BYXV0aD1CZWabcdefgSEVTNlpUVlFTUXZfblZfZ01FaDF6WWtSQ2kzb1d5RElFQ19mb2NmWG5Sam93RUlBYVJRTldfNwEB
AUTH XOAUTH2 abcdefgFuYUBnbWFpbC5jb20BYXV0aD1CZWabcdefgSEVTNlpUVlFTUXZfblZfZ01FaDF6WWtSQ2kzb1d5RElFQ19mb2NmWG5Sam93RUlBYVJRTldfNwEB
235 2.7.0 Accepted
NOOP
250 2.0.0 OK kl3sm6965596pbc.15 - gsmtp
Is SMTP still connected: true
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]
DEBUG SMTP: enable SASL
DEBUG SMTP: useEhlo true, useAuth false
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 587, isSSL false
220 mx.google.com ESMTP vo6sm6969236pbc.8 - gsmtp
DEBUG SMTP: connected to host "smtp.gmail.com", port: 587

EHLO E6410-PC
250-mx.google.com at your service, [xxx.xxx.xxx.xxx]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250 ENHANCEDSTATUSCODES
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
STARTTLS
220 2.0.0 Ready to start TLS
EHLO E6410-PC
250-mx.google.com at your service, [xxx.xxx.xxx.xxx]
250-SIZE 35882577
250-8BITMIME
250-AUTH LOGIN PLAIN XOAUTH XOAUTH2
250 ENHANCEDSTATUSCODES
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN XOAUTH XOAUTH2"
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: use8bit false
MAIL FROM:<[email protected]>
530-5.5.1 Authentication Required. Learn more at
530 5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 vo6sm6969236pbc.8 - gsmtp
DEBUG SMTP: got response code 530, with response: 530-5.5.1 Authentication Required. Learn more at
530 5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 vo6sm6969236pbc.8 - gsmtp

RSET
250 2.1.5 Flushed vo6sm6969236pbc.8 - gsmtp
DEBUG SMTP: MessagingException while sending
com.sun.mail.smtp.SMTPSendFailedException: 530-5.5.1 Authentication Required. Learn more at
530 5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 vo6sm6969236pbc.8 - gsmtp

    at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2114)
    at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1618)
    at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1119)
    at javax.mail.Transport.send0(Transport.java:195)
    at javax.mail.Transport.send(Transport.java:124)

QUIT
221 2.0.0 closing connection vo6sm6969236pbc.8 - gsmtp
com.sun.mail.smtp.SMTPSendFailedException: 530-5.5.1 Authentication Required. Learn more at
530 5.5.1 http://support.google.com/mail/bin/answer.py?answer=14257 vo6sm6969236pbc.8 - gsmtp

    at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2114)
    at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1618)
    at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1119)
    at javax.mail.Transport.send0(Transport.java:195)
    at javax.mail.Transport.send(Transport.java:124)

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