Question:

I set up a new Gmail/Google Apps account to receive tickets. It has stopped sending tickets, even though I've double-checked the password, and when I use the Test Settings button, the test passes. What's going on?

Answer:

This issue can be caused by Google's automatic anti-spam measures. Setting up a new account and then using it to relay a series of test messages can trigger this system.

A sign of this can be that you are asked to fill out a CAPTCHA test (where you have to enter distorted letters) when you log in to the account through the web, but that does not necessarily remove the block on sending.

To confirm that the anti-spam system is the problem, go to Admin > Email > Email Accounts and view the Outgoing Email Log.

If you see lines similar to this:

[2014-09-16 10:07:03 DEBUG] << 534-5.7.9 Please log in with your web browser and then try again. Learn more at534 5.7.9 https://support.google.com/mail/bin/answer.py?answer=78754 h2sm11326046qah.35 - gsmtp[2014-09-16 10:07:03 DEBUG] !! Expected response code 235 but got code "534", with message "534-5.7.9 Please log in with your web browser and then try again. Learn more at 534 5.7.9 https://support.google.com/mail/bin/answer.py?answer=78754 h2sm21536046qah.35 - gsmtp

try the following:

• Sign in to the Gmail/Google Apps account on the web (sign out then back in again if necessary).
• While signed in, go to http://www.google.com/accounts/DisplayUnlockCaptcha and verify that you are human.

If sending mail still doesn't work, you can work around the problem by connecting to Gmail via IMAP.