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Command Line Email FAQ—simple answers to complex questions.

My question

  • Q: When Command Line Email sends an email using Gmail's smtp server, the sending fails with the error message "Allow less secure apps". What does it mean?
  • A: Gmail considers regular email programs and backup programs to be "less secure", so in order for them to get access into your account, your "Allow less secure apps" option must be turned on.
    If you are a Google Workspace user, you can use App Passwords instead of your regular login credentials, all this without changing the "Allow less secure apps" setting.

Explanation

Before sending login credentials (a username and a password) to Gmail (smtp.gmail.com or smtp.googlemail.com), Command Line Email always establishes a secure connection (using SSL or STARTTLS commands). This is the way how automated email sending works. The server may not have a physical display where to show the password prompt.

Additional resources

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If you have any questions, please do not hesitate to contact our support team.