We are a Gmail site, why is it that some users send emails that do not make it out to the email list?

This can be for two reasons:

1. The user name and password for Gmail is either not set up or does not match what is entered on the user’s My Data > My Preferences screen.

2. The user’s Gmail settings does not have “Allow less secure apps” set to ON.

The Gmail system is set to recognize the SMTP Replay from iPASS as a Connected App or Site.

To fix the issues follow these steps

1. Go to Google Apps
2. My Account

3. Sign in and Security
4. Connected Apps and Sites

5. Allow Less secure apps needs to be set to ON

If this is left to OFF the system will not send the email and it is stopped for an authentication issue leaving iPASS with no indication to the user that it did not go.