Issue with setting up email: Job exception: Net::SMTPAuthenticationError

Obviously, this has something to do with my email configuration. I’m learning to setup my own Discourse instance, currently as a droplet in Digital Ocean. I have the instance setup, and it’s available at

I’ve gone through the troubleshooting doc with no luck:

I am looking to use my Google Workspace (gmail) account as my email provider. Here are my smtp email settings:

## TODO: List of comma delimited emails that will be made admin and developer
  ## on initial signup example ','

  ## TODO: The SMTP mail server used to validate new accounts and send notifications
  # SMTP ADDRESS, username, and password are required
  # WARNING the char '#' in SMTP password can cause problems!
  DISCOURSE_SMTP_PASSWORD: "myemailpassword"
  #DISCOURSE_SMTP_ENABLE_START_TLS: true           # (optional, default true)

  ## If you added the Lets Encrypt template, uncomment below to get a free SSL certificate

I also believe I followed Google’s docs correctly for SMTP relay:

Here are my settings from my Workspace > Gmail > Routing settings:

For anyone facing this issue, the solution ended up being to enable less secure apps in both my google workspace, as well as my individual account where I wanted the email to come from.

Step #4 on this topic:


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