使用OAuth和JavaMail发送电子邮件

Question

I have an Outlook.com email account. I want my Java app to be able to send emails from that email account using JavaMail. To do that, I've granted my app access via OAuth.

I have been able to successfully connect via IMAP using the wonderful sample app available in msgshow.java. However, I'm trying to send an email through my Outlook.com email account via SMTP and I'm not having any luck. I've tried using both the msgsend.java and smtpsend.java apps. However, I haven't had any luck. I tried:

java -Dmail.smtp.starttls.enable=true msgsend -d -M smtp-mail.outlook.com -U myAddress@outlook.com -P [oauthAccessToken] recipient@domain.com

which returned:

550 5.7.3 Requested action aborted; user not authenticated
DEBUG SMTP: got response code 550, with response: 550 5.7.3 Requested action aborted; user not authenticated

RSET
DEBUG SMTP: EOF: [EOF]
DEBUG SMTP: MessagingException while sending, THROW: 
com.sun.mail.smtp.SMTPSendFailedException: 550 5.7.3 Requested action aborted; user not authenticated
;
  nested exception is:
    com.sun.mail.smtp.SMTPSenderFailedException: 550 5.7.3 Requested action aborted; user not authenticated

    at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2202)
    at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1693)
    at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1194)
    at javax.mail.Transport.send0(Transport.java:254)
    at javax.mail.Transport.send(Transport.java:124)
    at msgsend.main(msgsend.java:188)
Caused by: com.sun.mail.smtp.SMTPSenderFailedException: 550 5.7.3 Requested action aborted; user not authenticated

    at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1700)
    ... 4 more

I also tried:

java -Dmail.smtp.starttls.enable=true smtpsend -d -A -M smtp-mail.outlook.com -U myAddress@outlook.com -P [oauthAccessToken] recipient@domain.com

I got:

DEBUG SMTP: Attempt to authenticate using mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM 
DEBUG SMTP: AUTH LOGIN command trace suppressed
DEBUG SMTP: AUTH LOGIN failed
Got Exception: javax.mail.AuthenticationFailedException: 535 5.0.0 Authentication Failed

How do you send email via JavaMail through Outlook.com using OAuth?

Thank you!

Answer 1

Did you see the instructions on the JavaMail wiki ? They show how to do it in Java, but you can do the same using msgshow.java by setting the properties on the command line, eg, "-Dmail.smtp.auth.login.disable=true".