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By upgrading, what do you mean? Upgrading the OS on the server or replacing the server with a new one?
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By upgrading, what do you mean? Upgrading the OS on the server or replacing the server with a new one?

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Adam, We want to upgrade from Windows server 2008 to Windows server 2016 by upgrading the OS on the server.
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Adam, We want to upgrade from Windows server 2008 to Windows server 2016 by upgrading the OS on the server.

Kasey Hart

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Is the OS 2008 and 32 bit? If it is, the process is simple, because you can't. If your starting point is actually 2008 R2, then it is 64 bit and upgrade is possible. If the OS is 2008 but 64 bit, then upgrade is possible.<br />
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That said, any machine running 2008 is likely physical and running on old hardware. I would highly recommend a fresh install as a VM on more modern hardware. What is the reasoning for wanting to do an in-place upgrade?
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Is the OS 2008 and 32 bit? If it is, the process is simple, because you can't. If your starting point is actually 2008 R2, then it is 64 bit and upgrade is possible. If the OS is 2008 but 64 bit, then upgrade is possible.

That said, any machine running 2008 is likely physical and running on old hardware. I would highly recommend a fresh install as a VM on more modern hardware. What is the reasoning for wanting to do an in-place upgrade?

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Do you have to take intermediate steps in upgrading to Windows server 2016, or can you upgrade directly?
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Do you have to take intermediate steps in upgrading to Windows server 2016, or can you upgrade directly?

Upgrading from Windows Server 2008 to Windows Server 2016

This topic area includes legacy versions of Windows prior to Windows 2000: Windows 3/3.1, Windows 95 and Windows 98, plus any other Windows-related versions including Windows Mobile.

Windows OS

The Microsoft Server topic includes all of the legacy versions of the operating system, including the Windows NT 3.1, NT 3.5, NT 4.0 and Windows 2000 and Windows Home Server versions.

Microsoft Server OS

Installation is the act of making a computer program program ready for execution. Because the process varies programs often come with a specialized program responsible for doing whatever is needed for their installation. Installation may be part of a larger software deployment process. Cross platform installer builders that produce installers for Windows, Mac OS X and Linux include InstallAnywhere, InstallBuilder and Install4J. Installers for Microsoft Windows include Windows Installer, InstallShield, and Wise Installation Studio; free installer-authoring tools include NSIS, IzPack, Clickteam, InnoSetup, InstallSimple and WiX. Mac OS X includes Installer, and also includes a separate software updating application.

Installation

Windows Server 2008 and Windows Server 2008 R2, based on the Microsoft Vista codebase, is the last 32-bit server operating system released by Microsoft. It has a number of versions, including including Foundation, Standard, Enterprise, Datacenter, Web, HPC Server, Itanium and Storage; new features included server core installation and Hyper-V.

Windows Server 2008

Windows 10 is a personal computer operating system featuring the "universal application architecture" (UAP); apps can be designed to run across multiple devices with nearly identical code, including PCs, tablets, smartphones, embedded systems, Xbox One, Surface Hub and HoloLens. Windows 10 also includes a virtual desktop system, a window and desktop management feature called Task View, the Microsoft Edge web browser, support for fingerprint and face recognition login, voice-based search (Cortana), new security features for enterprise environments, and DirectX 12 and WDDM 2.0 to improve the operating system's graphics capabilities for games.

Windows 10

Windows Server 2016 is the successor to Windows Server 2012 R2. Built upon the same core code as Windows 10, Windows Server 2016 brings enhancements in security, servicing, and connectivity. A particular focus on this release was hybrid-cloud scenarios, and has close ties to Azure and other Microsoft cloud initiatives. This does not detract from the many improvements that are available for on-premises-only deployments

Windows Server 2016 comes in Datacenter, Standard, and Essentials editions, and for servicing, has adopted windows 10's cumulative model. The new nano-server install is designed to be remotely managed and is designed to be kept current through continuous feature updates. The full GUI install operates similarly to windows 10's "Long Term Servicing Branch" (LTSB) model with cumulative security updates.

Windows Server 2016 has also shifted from a per-processor-and-CAL licensing model to a per-core-and CAL licensing model. This brings Windows Server's licensing more in line with Microsoft's other products and makes hybrid-cloud license planning easier as well.