You no longer need to open a ticket to request your Droplet to be booted into “Rescue Mode”, you may do it yourself via your DigitalOcean client area!

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.).

We, the volunteers here at 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.

Additional assistance is available via our community forums.

Tools You Need

DigitalOcean Account

DigitalOcean Droplet (Any Size)

Remote Desktop Client (RDP) – “Remote Desktop” Client is built into all Windows Operating Systems

The Guide