Gmail Not Sending (SMTP) Through Mac Mail App

[BillyBragg]

Greetings,

My organization uses Gmail through the Mac Mail app. Incoming emails are working, but outgoing/sending is not. Below is a log of my co-worker trying to send a message. I am kind of a noob and hoping for someone who can help translate.

OR maybe I am not even looking at the right log? 

Thanks!

[AEK · Accepted solution]

If I understand well you need to avoid inspecting port 587, right?

Then just add a policy above, for destination port 587, just without SSL inspection.

[BillyBragg]

Thank you for this, we are giving this a try. I'll let you know how it turns out, we'll need to test it and such. Thanks!

[BillyBragg]

This worked, below is the firewall policy. Thanks for the suggestion!

[AEK]

Your policy looks clean and perfectly tuned, like a good firewall admin would do.