To resolve the "535 5.7.8 Username and Password not accepted" error when setting up the "Send as" feature, you must use an App Password instead of your standard Google Workspace password.
Because less secure app access has been deprecated, Google Workspace no longer allows signing in to SMTP servers using your primary account password.
How to fix this:
- Enable 2-Step Verification: Make sure 2-Step Verification is enabled for your
@case.edu Google Workspace account.
- Generate an App Password:
- Navigate to your Google Account security settings.
- Under the "Signing in to Google" section, select 2-Step Verification and scroll down to App passwords.
- Generate a new app password (for example, select "Mail" and "Other" to name it "Gmail Send As").
- Update SMTP Settings:
- In your personal Gmail account's "Send mail as" configuration, set the server to
smtp.gmail.com.
- Use port 587 with TLS.
- Enter your complete
@case.edu email address as the username.
- Paste the generated 16-character App Password (without spaces) into the password field.
For more details, you can refer to the Google Account App Passwords guide"
Please note, this can be a little flaky, and you may need to repeat the process to get it to work.