Dear Tyler,
I got it! You shouldn't have to manually upload your certificate at all, everything should be done from the EAS Tool. Once you generate a new certificate, all you have to do is just choose the certificate validity.
Importing is only if you have your own. Once you generate new, then it's already being created by the console. So there is no need to import, just choose the certificate validity.
Sincerely,
J.R. Guthrie