When choosing an operating system to upgrade directly to Windows 2000 Server, which of the following operating systems can be upgraded in place?

Introduction / Context:
Understanding supported upgrade paths is essential when planning a migration to Windows 2000 Server. Not every earlier operating system can be upgraded in place; some require a clean installation. This question focuses on which legacy operating system can be upgraded directly to Windows 2000 Server while preserving user accounts, configuration, and applications. It is a common exam topic and highly relevant for administrators who must design realistic upgrade strategies.

Given Data / Assumptions:

You plan to deploy Windows 2000 Server in an existing environment.
Several older Microsoft operating systems are present, including desktop and server editions.
You need to know which one can be upgraded in place to Windows 2000 Server.
Upgrading in place means preserving users, configuration, and compatible applications as much as possible.
The candidate operating systems include Windows 95, Windows 98, Windows for Workgroups, and Windows NT Server 4.0.

Concept / Approach:
Windows 2000 Server is a server-class operating system and supports in-place upgrades only from compatible server products, primarily Windows NT Server 3.51 and Windows NT Server 4.0 with appropriate service packs. Desktop systems like Windows 95, Windows 98, and Windows for Workgroups are client operating systems and cannot be directly upgraded to Windows 2000 Server. Instead, they could potentially be upgraded to Windows 2000 Professional, but not to the server edition. Therefore, among the given options, only Windows NT Server 4.0 is an eligible in-place upgrade candidate for Windows 2000 Server.

Step-by-Step Solution:
Step 1: Separate the options into server and client operating systems. Windows NT Server 4.0 is server-class, while Windows 95, Windows 98, and Windows for Workgroups are client or workgroup systems. Step 2: Recall that Windows 2000 Server supports in-place upgrade from compatible versions of Windows NT Server, particularly NT Server 4.0 with the required service pack level. Step 3: Confirm that Microsoft does not support an in-place upgrade from Windows 95, Windows 98, or Windows for Workgroups directly to Windows 2000 Server. Step 4: Based on these facts, identify Windows NT Server 4.0 as the only option that can be upgraded directly to Windows 2000 Server.

Verification / Alternative check:
From a practical standpoint, think about the roles and features of each operating system. Windows NT Server 4.0 already participates in domain services, security, and server workloads similar in concept to Windows 2000 Server. Because of this similarity, an in-place upgrade path exists. Client systems such as Windows 95 and Windows 98 are designed primarily for workstation use and are upgraded to Windows 2000 Professional or later client versions, not server editions. This mental check confirms the conclusion.

Why Other Options Are Wrong:
Windows 95 – A client operating system, not supported for direct in-place upgrade to Windows 2000 Server.

Windows 98 – Another client operating system with an upgrade path to Windows 2000 Professional, not to the server edition.

Windows for Workgroups – A very old client-focused system that cannot be upgraded in place to Windows 2000 Server.

Common Pitfalls:
Some learners mistakenly think that any older Microsoft operating system can be upgraded to any newer version, but Microsoft restricts upgrade paths to realistic scenarios. It is also easy to mix up Windows 2000 Professional and Windows 2000 Server when thinking about upgrades. Always remember that server-class products tend to be upgraded from prior server versions, not from legacy desktop systems. On the exam, carefully read whether the question refers to Windows 2000 Professional or Windows 2000 Server.

Final Answer:
The only operating system in the list that can be upgraded directly in place to Windows 2000 Server is Windows NT Server 4.0.