I have all of my 450 classmates' high school graduation photos ready to upload for their "Then" photo. However I am struggling to see how to upload the photos via bulk upload. Certainly not wanting to do them one by one. Am I just not seeing something obvious? Hope so. All suggestions are much appreciated. Thank you.

Well, first off, classmate's graduation photos normally would be uploaded to their "YearBook" photos. "Then" photos are usually uploaded by the classmates themselves.
And unfortunately, as often as this has come up over the years, to my knowledge there is still no "bulk upload" feature or option for member photos. It took over a week for my co-admin and I to scan and upload all the yearbook photos for our class - and it's a relatively small class of 150.

Thank you for your reply.

Have uploaded all classmate yearbook photos to the appointed yearbook space. Not easy. I wish this could be done as part of the class list upload.

I have also unchecked the “then” photo option to avoid confusion. Classmates may still upload whatever other photos they wish to and label them however they like.

Lots of tweaking needed in many places it seems.