Gmail marking emails as potential spam / phishing

[ealong]

Opening this as an issue for my own organization.

Issue: Emails sent with script are marked with warning: "Be careful with this message. Gmail could not verify that it actually came from ____".

Some solutions:

• https://stackoverflow.com/questions/51198529/messages-sent-with-gmail-api-get-marked-as-suspicious-when-sending-to-gmail-addr

• https://stackoverflow.com/questions/14155604/avoid-gmails-this-message-may-not-have-been-sent-by-using-sender-header

^Neither solution is satisfactory to me because if you remove the From header, Gmail won't attach your display name to your email address. I do not believe these warnings are attached to my emails any longer though - after many script runs and student's interacting with these emails (and the tutor replying), Google's algorithm may no longer view them as a potential threat.

If anyone finds a more robust solution, please post it here. Thanks!

[gage117]

I ran into this same issue but I think it's actually just an issue during testing; at least it was for me. Either that or it is no longer an issue because of some change.

Explanation: I did some sleuthing and found this page which has a section that piqued my curiosity. It mentions that the warning will come up whenever the "To" and "From" address is the same, which is usually the case during testing.

"This warning will appear if:

• The domain in the "From" email address and "To" email address are the same. For example, if you're including internal team members on a campaign send, those recipients likely use the same domain as your "From" email address (@yourcompany.com). This will not happen if you send a campaign to a plain "@gmail.com" email address; contacts outside of your internal teams should not be affected. "

This led me to use an alternate email as the TEST_EMAIL variable in config.py so that the TUTOR_EMAIL and TEST_EMAIL were different email addresses. When testing it this way I can keep the From header the way we intend it and the warning doesn't appear. Changing the emails back to being the same prompted the warning to come back as it was before. This leads me to believe that none of the students will see the warning as it was only being triggered due to the "From" and "To" email addresses being the same.