Gmail smtp not able to send email javax.mail.AuthenticationFailedException:

Posted November 17, 2019 8.3k views

I have set gmail for less secure app already Also set IMAP forwarding

Locally sending emails works but the problem occurs in

digital ocean droplet [without ssl or domain] via ip address

Email Setting using java simple mail

private EmailMailer(){
        setMailer(new Mailer(new ServerConfig("", 587,EmailConstants.EMAIL_ID, EmailConstants.EMAIL_PASSWORD),

Checked Digital ocean was able to connect to port 587

Getting error while sending mail

Caused by: javax.mail.AuthenticationFailedException: 534-5.7.14 <
ww-app_1    | 534-5.7.14 ywow3CZ7TbpX5mHNs0LChqgXAsXoucspMfedy2oAIDqjP0MH4RO8M_1bLvhh6f3Ha0Fj_a
ww-app_1    | 534-5.7.14 RhfPx0WlDHIfsXUR8rbVLiSrSAr-hfc0PsOweMs0xMqQhHb6LhXMusyjtsfGzF> Please
ww-app_1    | 534-5.7.14 log in via your web browser and then try again.
ww-app_1    | 534-5.7.14  Learn more at
ww-app_1    | 534 5.7.14 a6sm8956026qth.74 - gsmtp
ww-app_1    | 
ww-app_1    |   at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(
ww-app_1    |   at com.sun.mail.smtp.SMTPTransport.authenticate(
ww-app_1    |   at com.sun.mail.smtp.SMTPTransport.protocolConnect(
ww-app_1    |   at javax.mail.Service.connect(
ww-app_1    |   at javax.mail.Service.connect(
ww-app_1    |   at javax.mail.Service.connect(
ww-app_1    |   at org.simplejavamail.mailer.internal.mailsender.MailSender.sendMailClosure(
ww-app_1    |   ... 59 more
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1 answer

Hello, @cbondy

Can you confirm if you have 2 factor authentication enabled as well? I had a similar case and I’ve needed to turn less secure app ON test my code and and then turn it off again.

Have you tried doing so?