send mail via SMTP Gmail Oauth2 issue

java smtp gmail smtp-auth google-oauth
kitokid picture kitokid · Dec 28, 2012 · Viewed 12.9k times · Source

I can authenticated to SMTP by following the google example.

But the problem now is I can't send out the mail. I am getting the following error whenever I try to send out mail.

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)

First I am getting can't connect to local host , thus I added a few lines of code to propery of session like below to OAuth2Authenticator class , still authenicated successfully. But can't send out the mail.

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

I am using the same session object and SMTP transport object which will be returned from OAuth2Authenticator class when I first authenticated successfully.

            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);

Full Debug Log

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)

Edited: I now called AUTH command explicitly like that .

 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);

but the response still the same.

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)

Answer

eddyparkinson picture eddyparkinson · Apr 15, 2013

Sorry people, answer is here: Javamail api in android using XOauth I tested, it works.

"SMS style login" failure - Secure accounts with 2 step login (via phone SMS) reject sending email via SMTP (both RAW password & OAuth style, fail with a Authentication error). They will let you create the OAuth token but will not send email.

Related questions

Using Javamail to connect to Gmail smtp server ignores specified port and tries to use 25

I'm trying to use javamail in a groovy script to send out an email via gmail. I've looked many places online and have been unable to get it working thus far. The error I'm getting when running my script is: …

Read More
javax.mail.AuthenticationFailedException: failed to connect, no password specified?

This program attempts to send e-mail but throws a run time exception: javax.mail.AuthenticationFailedException: failed to connect, no password specified? Why am I getting this exception when I have supplied the correct username and password for authentication? Both the …

Read More
Unable to send e-mail through Java

After going through post provided for the same problem, I have written the following code. But I am getting the following exception : javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 587; nested exception is: java.net.…

Read More