Installing Windows Server 2019 with IIS 10 on VMware Player

Setting up Windows Server 2019 with IIS 10 on VMware Player 17 allows you to create a robust and scalable server environment for testing, development, or even production use. By leveraging VMware Player 17’s capabilities, we can efficiently emulate a Windows Server environment without the need for dedicated hardware. This eliminates a significant amount of overhead and streamlines the installation process.

In my experience, VMware Player 17 provides a stable and user-friendly platform for running virtual machines. The installation process for Windows Server with IIS 10 is straightforward and can be completed with minimal hassle. This guide aims to walk you through the essential steps to get your server up and running quickly.

Virtualization with VMware Player 17 also enables easy backup and recovery processes, adding another layer of convenience and security to your setup. Whether you are setting this up for a lab, small business, or testing scenarios, this setup is both cost-effective and efficient.

I have already covered how to install WMware Player in a previous blog post so please install that first before following along here.


Downloading Windows Server 2019 Evaluation

You can download a trial copy of Windows Server 2019 free from the Evaluation Center. In my example I’m using the ISO file but they also offer a VHD.




What’s new with Windows Server 2019

Windows Server 2019 offers a robust array of features and benefits designed to enhance security, improve performance, and streamline management for modern IT environments. Key features include advanced multi-layer security measures, such as Windows Defender ATP and Shielded Virtual Machines, which help protect against sophisticated threats. The integration of hybrid capabilities with Azure simplifies cloud integration, enabling seamless management and scalability. Enhanced support for containers, including Kubernetes, accelerates application development and deployment. Additionally, Windows Admin Center provides a centralized, intuitive management interface, improving administrative efficiency. The operating system also boasts improved performance and reliability for demanding workloads, making it an ideal choice for organizations seeking a secure, efficient, and versatile server solution.


Before You Install Windows Server 2019

To install Windows Server 2019 without a license on VMware, first set up a new virtual machine with no initial software. Select I will install operating system later and click Next.




Select Microsoft Windows and then select Windows Server 2019. Click Next.


After setting up the empty VM, link it to the Windows Server 2019 ISO file. Once linked, restart the VM. This approach prevents VMware Player from prompting for a Windows license during setup.


Installing Windows Server 2019

After creating the virtual machine set the .iso file you downloaded and then start the virtual machine. As with every Windows installation you will be prompted to press any key to start the install. Once it starts you will be presented with the familiar Windows Server login screen. Select your options and click Next.



Select the edition you want and click Next. There will be another screen to accept the end user license. You have to accept that before proceeding.



Prepare your disk space as needed and click Next.



The installation goes quickly and you’ll be prompted to enter the administrator password.



Within a few moments from starting we’re ready to login to Windows Server 2019.



Installing IIS 10 on Windows Server 2019

To install IIS 10 on a new Windows server you have to use the Server Manager. Click Add Roles and Features.



From the Server Roles list select Web Server (IIS) and click Next.



On the next screen you’ll have the option to select specific features of IIS such as FTP, Request Filtering, and Authentication. Following best practices you should only select the options your server needs.



You can view the installation status progression. Click Close once complete.



Validating the Installation

To ensure IIS 10 is functioning correctly, open a web browser and type http://localhost. You should see the default IIS welcome page, which indicates that the web server is working properly.



Once installation completes. Open IIS Manager from the desktop icon or from Administrative Tools in the Control Panel. In case you did not know,  all of the IIS Manager’s settings are stored in C:\Windows\System32\Inetsrv\Config\applicationHost.config. If you’re new to IIS it’s always best to make a copy of the applicationHost.config file in case you need to restore it later.





VMware Shared Folders

Since your virtual machine is most likely installed on your PC you should take advantage of VMware Player’s shared folder feature. It allows you to share a local folder on you computer within the virtual machine. Before you can configure this however you have to install VMware Tools and that can be installed from the virtual machine’s settings.



Adding a shared folder to the virtual machine is just a matter of following the wizard and selecting the folder.



Select the folder you want to share.



Once the Shared Folder wizard completes you will then be able to see the new folder shared as the Z: drive.



Frequently Asked Questions about IIS 10

What is IIS 10?
IIS 10 (Internet Information Services) is a web server software developed by Microsoft for hosting websites and web applications. It is included with Windows Server 2016 and later, including Windows Server 2019.

How do I install IIS 10 on Windows Server?
You can install IIS 10 through the Server Manager by navigating to “Add Roles and Features” and selecting the Web Server (IIS) role. Follow the prompts to complete the installation.

What are the new features in IIS 10?
IIS 10 introduces several new features, including support for HTTP/2, Windows PowerShell Desired State Configuration (DSC), and enhanced security features like HSTS (HTTP Strict Transport Security).

How do I enable HTTP/2 in IIS 10?
HTTP/2 is enabled by default in IIS 10. However, it requires a secure connection (HTTPS). Ensure that your site is configured with an SSL certificate to utilize HTTP/2.

Can IIS 10 run on Windows 10?
Yes, IIS 10 can run on Windows 10. You can enable it through the “Turn Windows features on or off” dialog in the Control Panel by selecting Internet Information Services.

How do I manage IIS 10?
IIS 10 can be managed using the IIS Manager graphical interface, command-line tools like PowerShell, or through remote management tools such as the IIS Administration API.

What are the system requirements for IIS 10?
IIS 10 requires a compatible version of Windows Server (2016 or later) or Windows 10. Ensure your system meets the minimum hardware requirements for these operating systems.

How do I secure my IIS 10 server?
Securing IIS 10 involves several best practices, such as regularly updating the server, using SSL/TLS for encrypted communications, configuring firewalls, and employing security features like HSTS and request filtering.

Can I host multiple websites on IIS 10?
Yes, IIS 10 supports hosting multiple websites on a single server. You can configure multiple sites using different IP addresses, port numbers, or host headers.

How do I troubleshoot common issues in IIS 10?
Common issues in IIS 10 can be troubleshooted using tools like the Event Viewer, IIS



In conclusion, installing Windows Server 2019 with IIS 10 on VMware Player 17 is a remarkably straightforward process that can be completed with minimal hassle. By following our detailed walkthrough, you can set up a powerful server environment in just a few simple steps. From downloading and configuring VMware Player 17 to installing Windows Server 2019 and adding the IIS 10 role, each part of the process is designed to be user-friendly and intuitive. This guide demonstrates that even those with limited technical expertise can successfully create and manage a virtual server, underscoring the accessibility and efficiency of modern virtualization tools. Whether you’re setting up a test environment or preparing for a production server, our step-by-step instructions ensure a smooth and successful installation experience.

Peter Viola

Creative, customer focused, results oriented, Senior Web Systems Engineer who enjoys providing the highest level of customer service supporting complex Windows hosting solutions. MCITP, MCSA, MCTS

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