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”.

    1-digitalocean_create_droplet



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

    2-digitalocean-choose-distribution


  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.

    3-digitialocean-choose-droplet-size


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

    4-digitalocean-choose-a-datacenter-region


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

    5-digitalocean-hostname


  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.


    6-digitalocean-create


  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.

      7-digitialocean-support


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

      8-digitalocean-support-tickets


    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.

      9-digitalocean-create-ticket


    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.

      10-digitalocean-create-new-support-ticket


    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.

      11-digitalocean-support-ticket-response


  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”

      12-digitalocean-droplet-power-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”.


      13-digitalocean-droplet-turn-off


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


    3. Choose “Switch On”
      14-digitalocean-droplet-power-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

55 thoughts on “Installing Microsoft Windows onto DigitalOcean Droplet

  • November 30, 2016 at 11:14 pm
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    “I can not enter the character in the virtual keyboard, so I can not get in. How did you paste?

    Reply
  • December 2, 2016 at 12:52 am
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    Is it possible to do this on scaleway C2S?

    Reply
    • December 2, 2016 at 6:03 am
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      Unfortunately not at present, Scaleway doesn’t allow you to run your own kernel on either their VM’s or dedicated servers. As such there is no way to boot into Microsoft Windows.

      Reply
  • December 2, 2016 at 7:51 pm
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    The digital oceans have released additional disk space called volume. Can you share documents about adding these fields to windows?

    Reply
    • December 2, 2016 at 7:58 pm
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      That is certainly possible, will add it to the list of things to review.

      Reply
        • April 28, 2017 at 5:20 pm
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          Please create a thread in our forums for any/all requests.

          Thank you!

          Reply
  • December 9, 2016 at 3:52 am
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    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…

    Reply
    • December 9, 2016 at 5:19 am
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      Thank you for your kind words, glad it worked out well for you!

      Reply
  • December 11, 2016 at 7:44 am
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    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?

    Reply
    • December 11, 2016 at 4:13 pm
      Permalink

      It would theoretically be possible, however it may take some trial and error to do it.

      The primary things that come to mind..

      1. Force install VirtIO drivers (Assuming this is for Windows)
      2. Shrink the c:\ partition using Windows Disk Manager
      3. Live boot to Linux ISO/rescue mode
      4. Use DD to take a complete image of the disk
      5. Once you have your image you can install it to DigitialOcean similar to the above

      The biggest concern would be the fact your disk image may have issues due to it being a much larger physical disk when you are creating the image than you will have with your new Cloud Server/VPS.

      Feel free to post in the forums and I will advise where I am able.

      Reply
      • December 12, 2016 at 8:27 am
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        Thanks for the reply. I think you might be right in your assessments regarding this matter. There has to be an easy way to do this? We should definitely team up here to find a solution. If you find this case interesting of course.

        Reply
        • December 13, 2016 at 1:44 am
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          Please feel free to create a thread in the forums here and we will see what we can do.

          Reply
  • January 5, 2017 at 3:09 pm
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    I can’t login using RDC but can login in Droplet

    Reply
    • January 5, 2017 at 3:40 pm
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      Please double-check you completed step #23, you need to ensure you manually configure your Droplet’s IP address inside Windows before you will be able to connect with Remote Desktop (RDP).

      Reply
      • January 6, 2017 at 3:32 am
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        it connects to the VPS and I change my administrator password.In the droplet it worked but in RDC it tells me that my credential did not work

        Reply
        • January 6, 2017 at 3:58 am
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          Please create a new thread in our community forums.

          Reply
          • January 6, 2017 at 11:26 am
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            but need a help though.What ethernet should I manually configure? no.2 or 3?

  • January 27, 2017 at 6:09 am
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    Will upgrading the droplet from $5 to $10 or $20 break the installation?

    Reply
    • January 27, 2017 at 7:19 am
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      You shouldn’t have any issues upgrading.

      Once you have upgraded your Droplet you will need to manually expand your hard drive partition using Disk Management.

      Reply
      • January 27, 2017 at 11:39 am
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        The same applies for downgrading a droplet?

        Reply
        • January 27, 2017 at 1:24 pm
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          Yes & No, when you upgrade your Droplet you are given the option to increase your disk size or leave it as the current size. In order to downgrade in the future you will need to avoid upgrading the disk size and always keep it the same.

          Hopefully that makes sense.

          Reply
          • January 27, 2017 at 7:57 pm
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            So if a user is running a $20 droplet and they want to upgrade to any higher tier droplet, while maintaining their working windows installation, they need to make sure to choose the “CPU and RAM only” option when upgrading.

            Thanks for answering all these questions and for providing such an awesome workaround.

          • January 27, 2017 at 8:02 pm
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            This correct ONLY if the user wants to downgrade the Droplet in the future.

            You’re most welcome!

  • January 27, 2017 at 3:40 pm
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    This worked too well. You guys rock

    Reply
      • January 27, 2017 at 10:01 pm
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        I did hit 1 snag. Not your fault, but worth mentioning: You cannot snapshot the droplet and restore it later. Will not work. Talked to support and they said restoring a snapshot does linux-y things and if it cant do it, it will fail. So you must make these boxes one at a time and involve support for recovery iso.

        Reply
  • January 30, 2017 at 9:45 pm
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    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!!!!

    Reply
    • January 30, 2017 at 11:34 pm
      Permalink

      You’re welcome!

      Presently there aren’t any templates available for Windows 8/8.1, however I will be adding the trial versions in the future.

      The steps to building a template are rather involved unfortunately, I plan to write an article when I have time to do so.

      Reply
  • February 7, 2017 at 9:02 am
    Permalink

    gzip: stdin: unexpected end of life

    Reply
    • February 7, 2017 at 9:03 am
      Permalink

      Please create a thread in our community forums so we may assist you further.

      Reply
      • February 10, 2017 at 12:56 am
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        I got the same issue yet no clue to resolve this.

        Reply
        • February 10, 2017 at 1:25 am
          Permalink

          Please create a thread in our community forums so we may assist you further.

          Reply
  • February 12, 2017 at 3:53 pm
    Permalink

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

    Reply
  • February 15, 2017 at 1:29 pm
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    There is an problem in ISO LINKS!

    Reply
    • February 15, 2017 at 1:51 pm
      Permalink

      The download links for the templates have recently changed, however the mirrors are still very much online.

      In order to obtain the new download links you will need to submit a donation using the form just above the comment section here on this article. Once your donation has been received you will receive an activation link via email allowing you to access the remaining parts of the article and updated download links for each of the templates.

      More information here.

      Reply
  • February 16, 2017 at 1:28 am
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    please link
    i have bug, rebuild my vps please IHADP

    Reply
  • February 22, 2017 at 6:51 pm
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    the new number of cpu hasn’t detect by windows os when i resize the droplet.

    Reply
    • February 22, 2017 at 6:52 pm
      Permalink

      Please create a thread in our community forums.

      Reply
    • March 5, 2017 at 8:59 pm
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      Are you personally running into an issue? If so, please create a thread in the community forums so we may debug.

      Reply
  • March 6, 2017 at 5:49 pm
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    I don’t have any money and i really want to learn how to do this, please help me guys.

    Reply
  • March 16, 2017 at 8:40 am
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    Hi,
    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]

    Reply
    • March 16, 2017 at 12:43 pm
      Permalink

      The credentials you need to use when logging into Remote Desktop are outlined above; it will _not_ be the username & password received from DigitalOcean.

      Above in the guide where you ascertained the link to download/install the template you will find the login credentials directly below in a yellow box; the credentials vary from one template to the next in some cases.

      Reply
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  • September 25, 2017 at 11:51 pm
    Permalink

    Hello,

    I need some support. Download was going OK but suddenly it stopped with a message:

    no space left on device
    cannote write to ‘-‘ (broken pipe)

    Please advise
    Thanks

    Reply
    • September 26, 2017 at 1:52 am
      Permalink

      Please create a new thread in our forums ensuring you provide all the information requested in the sticky thread in the support section.

      Reply

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