Installing Microsoft Windows Operating System to DigitalOcean’s Droplet is impossible using conventional methods due to the inability to mount an installation ISO and lack of a KVM providing a virtual keyboard (ie. Send Ctrl + Alt + Del, etc.).
WhatUpTime have built special templates allowing Windows to be installed via DigitalOcean’s Recovery ISO; their Recovery ISO is available with all of their droplets, however you need to request it to be mounted via support ticket.
The guide below will walk you through the entire process, from beginning to end. Once you have reached the end of the guide your server will be successfully running Microsoft Windows Operating System.