[Legacy] Authentication Failed error when sending email notifications via Google

AVAILABLE TO CUSTOMERS ON:

When using a Google based email account to send email notifications in PaperCut NG & MF, you may run into the following error message:

Error sending email: Authentication failed; nested exception is javax.mail.AuthenticationFailedException: 534-5.7.14 
Please log in via your web browser and 534-5.7.14 then try again 
https://support.google.com/mail/answer/78754

The recommended, and most secure way, to correct this problem would be to enable 2-Step Verification on your Google Account and create an App Password.

Please note: 2-step Verification option will only be visible if your google administrator has it enabled for your organization.

To enable 2-Step Verification on the Google Account:

1. Go to your Google My Account settings
2. Click “Security” visible on the Navigation panel on the left
3. Under “Signing in to Google”, click “2-Step Verification” and follow the steps outlined by Google.

To enable App Passwords please follow the steps below:

1. Go to your Google My Account settings

2. Click “Security” visible on the Navigation panel on the left

3. Under “Signing in to Google”, click “App Passwords”. (You will need to have 2-step verification turned on for “App password” to be available.)

4. It would request you to sign in.

5. Then click on Select app, choose ‘Other (custom name)’.

6. A text box will appear to chose the name of the app. You could call it “PaperCut” or a name of your choice.

7. Click “Generate”. The app password will be generated. Copy the password.

8. Paste the password under Options → Notifications → SMTP server options. (See screeshot below)

An App password is a 16-digit passcode that gives an app or device permission to access your Google Account. More information about App Passwords can be found here: https://support.google.com/accounts/answer/185833

Security Concern

If you cannot enable 2-Step Verification and create an App Password, then you could create a siloed email address with a super long, super secure password, that is only used for email notifications in with PaperCut NG & MF.

Please note: This option will not be available if this has been turned off by your Google Administrator.

Turn on Allow less secure apps

The quick and easy (and not so secure) fix would be to turn on “Allow less secure apps” in your Google Account settings.

1. Go to your Google My Account settings
2. Click “Security”
3. Toggle “Allow less secure apps:” OFF → ON

You can find more information about the “Allow less secure apps” setting here: https://support.google.com/accounts/answer/6010255