Email Tracking Behavior when using Monday Squad

So I found this old post but it looks like it’s since been closed so i can’t add to it as I am having trouble doing something similar and I’m hoping the Community forum can help since I am a newbie user.

SCENARIO: I have a board that has all of our Contacts (both customers & vendors) because I’m treating it like our CRM. And I want the emails when I bcc: Squad for them to be tied to the Email Recipient AND to the accounts they are tied to. I want to first try to fix my first problem which is doesn’t seem to be saving the emails & updates consistently - they only get saved when the recipient responds back to me - why is that?