This is largely a solved problem. On Windows https://certifytheweb.com https://certifytheweb.com has provided automated certificate management for the best part

This is largely a solved problem. On Windows https://certifytheweb.com https://certifytheweb.com has provided automated certificate management for the best part of a decade and we're now branching out into large scale cross-platform tools, for those interested. I was surprised by a customer yesterday who was looking to migrate thousands of manually renewed 1 year certs, I had no idea people were still using 1 yr certs to such a broad degree.