Gmail SMTP not accepting credentials from Jira

[Hermeus Corporation]

When setting up an email via SMTP to send emails from Jira, authentication is not working.

A little background on my Gmail setup

• Using Gsuite account (user, not admin)
• Two-factor authentication is turned on
• "Less secure apps" are allowed
• Application-specific password setup for Jira

When logging in with my regular account password, I get the following error:

Unfortunately no connection was possible. Review the errors below and rectify:

• AuthenticationFailedException: 534-5.7.9 Application-specific password required. Learn more at 534 5.7.9 https://support.google.com/mail/?p=InvalidSecondFactor d123sm96315ywb.11 - gsmtp

When logging in with my application-specific password, I get the following error:

Unfortunately no connection was possible. Review the errors below and rectify:

• AuthenticationFailedException: 535-5.7.8 Username and Password not accepted. Learn more at 535 5.7.8 https://support.google.com/mail/?p=BadCredentials z6sm4341608ywg.40 - gsmtp

When logging in with an incorrect password:

Unfortunately no connection was possible. Review the errors below and rectify:

• AuthenticationFailedException: 535-5.7.8 Username and Password not accepted. Learn more at 535 5.7.8 https://support.google.com/mail/?p=BadCredentials x4sm2253722ywc.89 - gsmtp

When I change my Gmail account setup to deactive 2-factor authentication, I get the following error (logging in with regular account password):

Unfortunately no connection was possible. Review the errors below and rectify:

• AuthenticationFailedException: 535-5.7.8 Username and Password not accepted. Learn more at 535 5.7.8 https://support.google.com/mail/?p=BadCredentials z6sm4341608ywg.40 - gsmtp

Any thoughts on other things to try, either on the Gmail side or the Jira side? FWIW, I have the same issues in Confluence.

[Patrick]

Hi @Hermeus Corporation ,

I was just having the same issue and I was able to do it by "enforce access to less secure apps for all users (not recommended)".  I am also the admin for my gsuite account.

Hope this helps.

[brbojorque]

Maybe it is locked due to multiple incorrect logins.