Installing Windows Server

AlphaCMD IT Posts, Windows

What is used for this example:

  • Virtual machine running on ESXi 6.5
  • Server 2016 ISO installation media
  • Server 2016 installation process.

Requirements for installing windows Server 2008 & later:

  • Bare Metal installations
    • Hardware that has at least 4GB of RAM, 40GB of storage.
    • USB or DVD with Windows Server installation media 
    • Hardware is booted from the USB/DVD
  • Virtual Machine Requirements
    • ESXi 6.0 or later recommended
    • 40 GB of storage available on the ESX host
    • 4GB of available RAM
    • Windows server installation ISO uploaded to an accessible ESX data store
    • Installation media is attached to the VM’s CD/DVD ROM.

How-to posts for all listed requirements:

  • Creating Physical Installation media for Windows and Linux (Post coming Soon)
  • Building Virtual Machines in vSphere (Post coming soon)

Installation Process:

When the server is booted into the installation media, you should see a screen very similar to this.

Verify that the language, time, currency and keyboard types are correct. In most cases, the default should be correct. Select Next when all fields are correct.

Server 2016 installation – Begin installation Screen

The next window will present 2 options. 

Option 1: Install now – This will allow you to start the installation process for a new server.

Option 2: Repair your computer – This is normally only used when an existing installation of windows is having severe issues and the only way to retrieve information, repair or restore the server is from installation media.

Select “Install Now” to continue.

Server 2016 installation – Install Now Screen

This will bring you to the licensing screen. If you’ve purchased a license key, input that here. If not, select “I don’t have a product key” to continue with the installation. This will allow you to install Windows Server under an evaluation license.

Server 2016 installation – Lisence Screen

When you click on either next or “I don’t have a product key”, you will be brought to the “Select the operating system you want to install”.

With the full installation ISO, when selecting “I don’t have a product key”, you should have 4 options:

Server 2016 Installation – Select an OS screen

There are two major variations of Windows Server 2016: Standard & Datacenter. The main difference between the two is that Standard has less functionality in relation to Hyper-V and Software defined networking. A full and detailed list of differences can be found on Microsoft’s website here.

The other two variations are the difference between “desktop experience” & Windows Server Core installation. Desktop experience installs the full GUI that you’re likely familiar with. You’ll have a full desktop environment just like Windows 10 (or 7/8 depending on your version of windows server). Server Core, will install just the OS and you will only have command line (PowerShell in this case) access.

For this post, I’m just using the evaluation license and will be installing Server 2016 Datacenter Desktop Experience. 

When you’ve selected your version of Windows Server click next.

The following screen will bring up the license terms agreement. You will have to check the box to proceed to the next step.

After the license screen the following will ask you what type of installation you would like to complete. Upgrade or Custom. Given that we don’t have an older version of Windows Server installation that we are intending to upgrade, choose Custom.

This screen will show you the available drives that Windows can see and be installed on. In this example, the drive that is available is a brand new disk created with the virtual machine. This will be a drive that has “Unallocated Space”, as shown in this screen shot.

If the disk that you’re attempting to install Windows on is formatted, the attempt will likely fail. You can remove all partitions for the target installation disk by selecting the partitions for each drive, then selecting the delete button.

If you’re working on a bare metal installation and you don’t see the target disk, there could be a few potential issues. The most common of which are missing non-standard drivers, hardware failure, or. 

Given that your target installation disk is showing as unallocated space, you are ready to continue. Unless you’re doing something special, you do not need to manually create new partitions. The installer will do everything that for you.

Simply, select your target disk for installation and hit “next”. This will begin the installation. Upon completion of the installation, the server will automatically reboot.

Server 2016 Installation – Installation in progress

If you’re doing a bare metal installation, make sure that either the installation media is removed when the server bios screen comes up, or make sure that your boot order settings are set so that the disk the new windows installation is on, takes priority over your installation media. If you reach the screen from step 1, you’ve booted back into the installation media and not into the new windows installation.

Server 2016 Installation – Automatic Reboot

Post Installation

When the server has completed the boot process, the first thing that will come up is the request for you to set the administrator password. Fill in both of these fields to meet the complexity requirements. For production servers, it is recommended that a password is randomly generated from a secure password manager. 

When you’ve set this password you will be brought to the login screen. The base installation of your Windows server is complete. However, there are normally some post installation requirements that need to be completed before the server will be useable. Generally, these consist of driver installations and system updates.

For bare metal installations, you may experience network or other hardware issues caused by Windows missing the necessary drivers to control the network card. You will need to use a flash drive to transfer the vendor’s drivers to the server for installation.

For virtual machines (In this case, VMware), you will need to install VMware tools before all of the virtual hardware will properly work. To begin this installation, login to the server. Server manager will pop up; you can close this window or just ignore it. 

Open a browser on your local desktop, and open up your vSphere management page and login. When you’ve logged in, navigate to and right click on your new virtual machine. Within this menu, go to Guest OS and then select “Install VMware Tools”.

Server 2016 Post Installation – VMware Tools Installation

Back in your Windows Server VM, the VMware tools installation media will now be mounted to the server.

To begin the installation, open up file explorer and navigate to This PC. Then simply double click on the VMware tools DVD Drive option to bring up the installer.

Server 2016 Post Installation – VMware Tools Installer

When the installer window comes up, hit next to get past the welcome screen. You will be given 3 options:

  1. Typical
  2. Complete
  3. Custom

For a normal server, Typical is the best selection. Complete is only necessary if you intend to host VMware product services on this server, such as vCenter. 

Server 2016 Post Installation – VMware tools setup type

Hit “next” when you’ve selected your choice of installation type, then hit install to being the installation. During this installation you should see your network adapter, and screen reset several times.

Server 2016 Post Installation – VMware tools installation in progress

When the installation is complete, hit “finish”. This will request a reboot. Select “Yes” to reboot the server. 

Server 2016 Post Installation – Reboot request

The last step to complete the basic configuration for Server 2016 is to install updates. When your server has completed the reboot, Login. From there, open the start menu and select the small gear on the left hand side to open the settings app. 

Server 2016 Installation – Start menu settings

When the settings app opens, select the tile for “Update & Security”

Server 2016 Post Installation – Settings Window

When this opens simply hit the “Check for updates” button. The remainder of this process can take several hours. When it does find what updates need to be installed, it will begin downloading and installing the updates automatically. 

Server 2016 Post Installation – Updates In progress

When this process is complete, there will be a button to restart and complete the installation of the updates. To complete the update cycle, select “install now” or any other related option given by the server. When all updates have been completed, your settings window should say “Your device is up to date.”