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

The Guide

  1. Log In – Log into your DigitalOceans Control Panel.

  2. Create Droplet – Once you have logged in, you will need to choose “Create Droplet”.


  3. Choose an Image – Ubuntu 16 is recommended, however any Operating System may be chosen.


  4. Choose a Size – The template will successfully install to all size Droplets, however depending on your workload you may need a larger size due to CPU & RAM needs.


  5. Choose a Datacenter Region – You may choose any location you desire to have your Droplet located.


  6. Choose a Hostname – Here you will choose the name for your Droplet.


  7. Create – Once you have selected the operating system, size and location for your Droplet you will need to choose “Create” at the bottom of the page.


    As you may have noticed there were additional options on the Droplet creation page, please ensure to do NOT choose “Backups” or “User Data” as they may interfere with the installation of Microsoft Windows and cause the installation to fail.

    You can certainly enable “IPv6” and “Private Networking”, both should work without issue once Microsoft Windows has been installed.


  8. Recovery ISO & Support Ticket – Once your Droplet has been successfully created a support ticket will need to be created to request DigitialOcean’s Recovery ISO be mounted to your Droplet.

    1. Locate Support Ticket Creation Page – Choose “Support” at the top of DigitalOcean’s control panel webpage.


    2. Support Tickets – Once you are inside DigitalOcean’s “Support Center” you need to choose “Support Tickets” at the top right of the page.


    3. Create Ticket – Depending on the age of your account you may need to choose “Create Ticket” (Blue Button) at the top right of the control panel web page.


    4. Create New Support Ticket – Once you have arrived on the “New Support Ticket” page inside DigitialOcean’s control panel you will need to fill in the page similar to the following screenshot.


    5. Submit Ticket – Once you have completed filling in the Support Ticket Request to be similar to the above screenshot you will need to choose “Submit Ticket” (Blue Button) at the bottom right of the page.

      Depending on the time of day it may take several hours for DigitalOcean’s Support Team to respond to your Support Ticket.

    6. Ticket Response – DigitalOcean’s Support Team will eventually respond to your ticket noting the Recovery ISO has been mounted to your Droplet.


  9. Power Off & Power On Your Droplet – Once the recovery ISO has been mounted for you by DigitalOcean’s Support Team you will need to power your Droplet off and then power it back on all via their web control panel.

    1. Choose “Switch Off”


    2. Choose “Turn Off” – When you have chosen “Off / Switch Off” you will be presented with an warning message providing some good information. I would recommend reading the message thoroughly so you are well informed for the future.
      When you have read the entire message continue by choosing “Turn Off”.


      It will take a few moments for your Droplet to completely power off.

    3. Choose “Switch On”

      As with powering off, it will take a few moments for your Droplet to power on.

  10. Accessing Your Droplet’s Console – DigitalOcean provides console access for all of their Droplets (It provides similar access to have a monitor, keyboard and mouse attached) which will be used to install Microsoft Windows onto your Droplet.

    1. Opening the Console – Choose “Console” at the top, right side of DigitalOcean’s web control panel for your Droplet.15-digitalocean-click-console

    2. A New Browser Windows Opens – Once you have chosen “Console” as detailed above a new browser window will open presenting you with your Droplet’s console.

      In the event your console windows doesn’t look nearly identical to the above you will want to respond to your Support Ticket requesting assistance from DigitalOcean’s Support Team in regards to booting your Droplet into the recovery ISO.

  11. Access Interactive Shell – Your recovery environment now has network access allowing us to continue with the downloading and installation of Microsoft Windows to your Droplet.
    Choose “6” on your keyboard to choose option #6 (“Interactive Shell [/bin/bash]”) and then choose “Enter” on your keyboard to run the command.

  12. Installing Microsoft Windows – To begin the Windows installation you will need to input the following command into your Droplet’s console. Please ensure the command matches perfectly otherwise your installation will likely fail.

    Installing Microsoft Windows onto DigitalOcean Droplet

Leave a Reply

53 Comments on "Installing Microsoft Windows onto DigitalOcean Droplet"

Notify of
Sort by:   newest | oldest | most voted

“I can not enter the character in the virtual keyboard, so I can not get in. How did you paste?


gunzip | <—- this character


Is it possible to do this on scaleway C2S?


The digital oceans have released additional disk space called volume. Can you share documents about adding these fields to windows?

Brian Jacobs

A detailed and easy to follow guide. Covers everything. Digital Ocean responded very fast to my service requests. Three hours from creating new droplet to connecting via Remote Desktop Connection…

Great write-up! I’m wondering if there is a way to move an existing installation (physical or virtual) onto the cloud? Would be great if I could move a couple of my servers and boot them up so they run as a droplet on DigitalOcean.

Any thoughts about this?


I can’t login using RDC but can login in Droplet


Will upgrading the droplet from $5 to $10 or $20 break the installation?


This worked too well. You guys rock


Wow! this was amazing!!!
Thank you!!!!

now… I must ask, do you have a Windows 8 VL template?? because I have a license for it…

If not, what are the steps to build an image?

Thank you again!!!!


gzip: stdin: unexpected end of life


Windows 10 in vps linux 🙂 dream thank you all, I can not get the internet to work please tutorial

Victor Hugo

There is an problem in ISO LINKS!


please link
i have bug, rebuild my vps please IHADP


the new number of cpu hasn’t detect by windows os when i resize the droplet.


lol 8 cpu only detect 2 xD

Angelo De Vega

I don’t have any money and i really want to learn how to do this, please help me guys.


I successfully completed Step #23 (my droplet can connect to the internet now in the console) but when I try using RDP, it just won’t log in. Is this how I am supposed to input my credentials?
Computer: [my droplet’s public IP]
User name: root
Password: [the password when I created my droplet]


[…] Installing Microsoft Windows onto DigitalOcean Droplet […]