Blocked Remote Proxy with kids Google Classroom

[jj's_4701]

I have been testing/running pfsense on a SBC for months, but once remote learning started, I had to switch back to my old Name-brand router.
Our school district is using a cloud proxy service for student traffic.
Pfsense was blocking all the SSL traffic with Google Classroom, which I assume was triggering a Man-in-the-middle-SSL hack.
Is this manageable? My searches and document reading hasn't pinpointed to a solution.
I bought the Netgate-2100 hoping to utilize the 30-day support and solve this. I thought the forum would be a better start to finding a solution.