How to Install Windows Server 2019 on VPS?

In this article, we will take a detailed look at the process of installing Windows Server 2019 on a Virtual Private Server (VPS). You will learn about the key steps of preparation, selecting a suitable image, configuring the network, and performing the initial configuration of the operating system. Step-by-step instructions and practical examples will help you successfully complete the installation and configure your server for further work. We will also discuss common errors and how to resolve them.

Table of Contents:

Choosing a VPS Provider and Preparation

How to Install Windows Server 2019 on VPS? - Description of the process of choosing a VPS provider and the steps to prepare for installing Windows Server 2019, including resource requirements.
The first step is to choose a reliable VPS provider that offers the ability to install your own operating system. It is important to make sure that the provider provides access to the server management console via VNC or KVM, which is necessary to install Windows Server 2019 from an ISO image. Pay attention to the following factors:
  • Cost: Compare prices from different providers, considering included traffic, RAM, disk space, and CPU resources.
  • Reputation: Read customer reviews about the reliability and quality of the provider’s support.
  • VNC/KVM Access: Make sure that the provider provides convenient access to the server console.
  • ISO Upload Capability: Some providers allow you to upload your own operating system ISO images.
  • Server Location: Choose a server located geographically close to your users to ensure minimal latency.
After choosing a provider, you need to decide on the server configuration. Minimum requirements for Windows Server 2019:
  • Processor: 1.4 GHz 64-bit processor
  • RAM: 2 GB RAM
  • Disk Space: 32 GB
  • Network Adapter: Gigabit Ethernet
For more comfortable work, it is recommended to increase the amount of RAM and disk space, especially if you plan to run resource-intensive applications. Example 1: Comparing VPS Providers
ProviderCost (per month)RAMDiskTrafficVNC/KVM
DigitalOcean$204 GB80 GB4 TBYes
Vultr$204 GB80 GB3 TBYes
Linode$204 GB80 GB4 TBYes
This example compares three popular VPS providers based on key parameters. DigitalOcean, Vultr, and Linode provide similar characteristics, so the choice depends on personal preferences and support reviews. Example 2: Preparation for Installation
  • Register on the website of the chosen VPS provider.
  • Create a new VPS with the selected configuration. (Do not select a pre-installed OS).
  • Get access to the VNC/KVM console of the server. This information is usually available in the VPS control panel.
  • Prepare the Windows Server 2019 ISO image. (The next section describes in detail how to do this).
Expert Tip: Before creating a VPS, check with the provider about the possibility of installing Windows Server 2019 and the necessary steps for uploading the ISO image. Some providers may have restrictions or special instructions.

Obtaining the Windows Server 2019 ISO Image

How to Install Windows Server 2019 on VPS? - Description of the process of downloading the Windows Server 2019 ISO image from the Microsoft website or using another trusted source, with an emphasis on licensing aspects.
To install Windows Server 2019 on a VPS, you will need an ISO image of the operating system. There are several ways to obtain it:
  • Official Microsoft Website: The most reliable way is to download a trial version from the Microsoft website. It allows you to use Windows Server 2019 for 180 days for familiarization and testing. To continue using it, you will need to purchase a license.
  • MSDN Subscription (Visual Studio Subscription): If you have an MSDN subscription, you can download licensed Windows Server 2019 ISO images.
  • Microsoft Partner Programs: Special ISO image download channels are available for Microsoft partners.
Example 1: Downloading a Trial Version from the Microsoft Website
  • Go to the Windows Server 2019 trial version download page: https://www.microsoft.com/ru-ru/evalcenter/evaluate-windows-server-2019
  • Fill out the form with the necessary information.
  • Select the ISO image to download. Pay attention to the language and edition (Standard or Datacenter).
  • Wait for the download to complete. The ISO image size can be several gigabytes.
After downloading the ISO image, make sure that it is not corrupted. You can check the checksum (MD5, SHA-1, SHA-256) of the file. Information about checksums can be found on the Microsoft website. Example 2: Checking the Checksum of the ISO Image
# PowerShell (Windows)
Get-FileHash -Algorithm SHA256 -Path "C:\path\to\your\WindowsServer2019.iso"

# Linux
sha256sum /path/to/your/WindowsServer2019.iso
These commands will calculate the SHA256 hash of your ISO image. Compare the resulting hash with the value specified on the Microsoft website. If they match, the image is not corrupted. Replace «/path/to/your/WindowsServer2019.iso» with the actual path to your file. Example 3: Uploading the ISO to the VPS After obtaining the ISO image, it needs to be uploaded to your VPS. The upload methods depend on the capabilities provided by your VPS provider. Some providers offer the ability to upload ISO images directly through the control panel. If this is not possible, you can use the `wget` utility (if Linux is installed on the VPS) or SFTP.
# Linux (on VPS)
wget https://example.com/WindowsServer2019.iso
Replace `https://example.com/WindowsServer2019.iso` with the URL where your ISO image is available. Make sure you have enough free disk space on the VPS to accommodate the ISO image. Important: Use only licensed Windows Server 2019 ISO images. The use of unlicensed software is a violation of copyright and may result in legal consequences.

Installing Windows Server 2019 via VNC or KVM

After uploading the ISO image to your VPS, you need to boot the server from this image. The process may vary slightly depending on your VPS provider, but usually looks like this:
  • Open the VNC/KVM console of your VPS.
  • Reboot the VPS. (Sometimes you need to stop and start the VPS).
  • During boot, enter the BIOS/UEFI. Usually, you need to press the `Delete`, `F2`, `F12`, or `Esc` key. Information about the key to press is displayed on the screen during boot.
  • Change the Boot Order in BIOS/UEFI. Specify that the first device to boot should be CD-ROM/DVD-ROM, which will emulate your ISO image.
  • Save the changes and exit the BIOS/UEFI. The VPS will reboot and try to boot from the ISO image.
If everything is done correctly, you will see the Windows Server 2019 boot screen. Then follow the instructions on the screen:
  • Select the language, time format, and keyboard layout.
  • Click «Next».
  • Click «Install».
  • Enter the product key. If you do not have a product key, you can select the «I don’t have a product key» option and continue the installation in trial mode.
  • Select the Windows Server 2019 edition. It is recommended to choose «Windows Server 2019 Standard (Desktop Experience)» or «Windows Server 2019 Datacenter (Desktop Experience)» for ease of use. «Desktop Experience» means that a graphical user interface (GUI) will be installed.
  • Accept the terms of the license agreement.
  • Select the installation type: «Custom: Install Windows only (advanced)».
  • Select the disk to install Windows on. If the disk is clean, it needs to be formatted.
  • Wait for the installation to complete. The VPS will reboot several times.
Example 1: Changing the Boot Order in BIOS (using AMI BIOS as an example)
  • Enter the BIOS (press Delete during boot).
  • Go to the «Boot» tab.
  • Find the «Boot Device Priority» or «Boot Order» option.
  • Use the «+» and «-» keys or the up and down arrows to move CD-ROM/DVD-ROM (or the device that emulates the ISO image) to the first place in the list.
  • Go to the «Exit» tab.
  • Select «Save Changes and Exit».
Example 2: Installing Drivers (if necessary) In some cases, Windows Server 2019 may not recognize the network adapter or disk of your VPS. In this case, you will need to install drivers. Drivers are usually provided by your VPS provider. You can download the drivers to another computer, and then upload them to the VPS via VNC/KVM (sometimes VNC/KVM provides the ability to mount a local disk). During Windows installation, select «Load Driver» and specify the path to the folder with the drivers. Example 3: Selecting a Disk for Installation At the stage of selecting a disk to install Windows Server 2019, you will see a list of available disks. If the disk is clean, it will be displayed as «Unallocated Space». Select this disk and click «New». Specify the size of the partition (it is recommended to use the entire disk). Click «Apply». Windows will create a system partition and a data partition. Select the partition that will be used to install Windows (usually the largest partition) and click «Next».

Initial Configuration of Windows Server 2019

After the installation of Windows Server 2019 is complete and you boot for the first time, you will be prompted to set a password for the administrator account. Be sure to use a strong password consisting of upper and lower case letters, numbers, and special characters. Next, you need to perform the initial server configuration:
  • Network Configuration: Configure the IP address, subnet mask, gateway, and DNS servers. This information is usually provided by your VPS provider.
  • Installing Updates: Install the latest Windows updates to ensure the security and stability of the server.
  • Firewall Configuration: Configure the Windows firewall to allow access only to the necessary ports and services.
  • Installing the necessary software: Install the necessary software for your tasks (e.g., web server, database, etc.).
Example 1: Configuring the IP Address
  • Open «Network and Sharing Center».
  • Click «Change adapter settings».
  • Right-click on your network adapter and select «Properties».
  • Select «Internet Protocol Version 4 (TCP/IPv4)» and click «Properties».
  • Select «Use the following IP address».
  • Enter the IP address, subnet mask, gateway, and DNS servers provided by your VPS provider.
  • Click «OK».
Example 2: Installing Windows Updates
  • Open «Settings».
  • Select «Update & Security».
  • Click «Check for updates».
  • Wait for the search and installation of updates to complete.
  • Reboot the server if required.
Example 3: Configuring the Windows Firewall
  • Open «Windows Defender Firewall with Advanced Security».
  • In the left pane, select «Inbound Rules».
  • Click «New Rule…» in the right pane.
  • Select «Port» and click «Next».
  • Select «TCP» or «UDP» (depending on the protocol you want to allow).
  • Enter the port number (e.g., 80 for HTTP or 443 for HTTPS).
  • Select «Allow the connection» and click «Next».
  • Select the profiles for which you want to apply the rule (usually «Domain», «Private», and «Public»).
  • Enter a name for the rule and click «Finish».
Expert Tip: After installing Windows Server 2019, it is recommended to install antivirus software and regularly scan the server for malware.

Activation and Updates

After completing the initial configuration, you need to activate Windows Server 2019. Activation confirms the legality of using the operating system and provides access to all functions and updates. Activating Windows Server 2019
  • Using the Graphical Interface:
    • Open «Settings».
    • Go to «Update & Security».
    • Select «Activation».
    • If Windows is not activated, click «Change product key» and enter your product key.
  • Using the Command Line:
    • Open the command prompt as an administrator.
    • Enter the command: slmgr /ipk <your_product_key> (replace <your_product_key> with your actual key).
    • Enter the command: slmgr /ato
After entering the product key and executing the command `slmgr /ato`, Windows Server 2019 will attempt to activate over the Internet. Make sure your VPS has Internet access. Configuring Automatic Updates To ensure the security and stability of the server, it is recommended to configure automatic updates.
  • Using the Graphical Interface:
    • Open «Settings».
    • Go to «Update & Security».
    • In the «Windows Update» section, click «Advanced options».
    • Turn on the «Automatically download and install updates» option.
  • Using Group Policy:
    • Open the Local Group Policy Editor (gpedit.msc).
    • Go to «Computer Configuration» -> «Administrative Templates» -> «Windows Components» -> «Windows Update».
    • Find the «Configure Automatic Updates» setting and enable it.
    • Configure automatic update settings according to your needs.
Example 1: Checking Activation Status
# Command line (as administrator)
slmgr /xpr
This command will display information about the Windows Server 2019 activation status. If Windows is activated, you will see the message «Windows(R), ServerStandard edition is permanently activated». Example 2: Configuring Automatic Installation of Updates at a Specific Time You can configure automatic installation of updates at a specific time to minimize the impact on server performance. To do this, use Group Policy.
  • Open the Local Group Policy Editor (gpedit.msc).
  • Go to «Computer Configuration» -> «Administrative Templates» -> «Windows Components» -> «Windows Update».
  • Find the «Configure Automatic Updates» setting and enable it.
  • Select the option «4 — Auto download and schedule the install».
  • Specify the day and time to install updates.
Important: Regular installation of Windows updates is critical to ensuring the security and stability of your server. Do not disable automatic updates unless absolutely necessary.