Which Windows edition should I choose?

In this article:

Which Windows edition should I choose?
- Windows client editions
- Windows server editions

Windows editions follow a naming convention which may not be the clearest and, to make things worse, change with Windows versions and cover both technical and non-technical differences (meaning that two different editions may actually be the same with just a different EULA).

Here is a short post on main Windows editions with a focus on the version you may prefer for your lab.

Windows client editions

Windows Home or Core edition is the low-budget, consumer grade version of Windows. It is enough for home uses, but is missing features necessary for corporate environments such as the ability to join an Active Directory domain.
Windows Professional or Business edition adds more functionalities, such as the ability to join an Active Directory domain and disk encryption (limited to the Enterprise edition and above until Windows 7 included).
Windows Enterprise, Education and Ultimate editions are the most complete editions. There is little to no technical difference between them, the main difference being the distribution channels and the licensing.
Other editions are also available for mobile and low-power devices, they are usually even more limited than the Home edition.

Only the first two and the Ultimate (which existed only for Windows 7) are available as retail version, the others either need a specific contract with Microsoft or are provided pre-installed by devices manufacturers.

Wikipedia has good charts allowing to compare the feature available in each editions:

The evaluation versions of the Enterprise edition of recent Windows systems are freely downloadable from Microsoft website.

Windows server editions

Windows Server Essentials (formerly Windows Small Business Server) is a low-budget version of Windows Server. Several functionalities are locked and a specific dashboard is available to make management easier¹. See here for more information. With older Windows version a Windows Server Foundations existed which was even more limited than Windows Server Essentials.
Windows Server Datacenter edition is focused on large infrastructures and focuses on performances. This includes changes in the systems, in the functionalities (some may be reduced) and in the prerequisites (the linked post mentions a minimum of eight CPUs). See here for more information.
With modern Windows versions, Windows Server Standard edition, or simply Windows Server is what you usually want when you simply want to test Windows Server features.
Up to Windows 2008 included, a Windows Server Enterprise was also available. This one was the complete version and Windows Server standard was an intermediary between Windows Server Small Business and this one. From Windows 2012 on Windows Server Enterprise has been merged into Windows Server Standard. See here for more information.

Recent versions of Windows server can be installed either with or without the GUI (also called Desktop Experience). On the same idea, Windows 2008 Standard, Enterprise and Datacenter also proposed a minimal installation mode as Server Core to reduce your vulnerability footprint (more information)

As with Windows client systems, evaluation versions of the Standard edition and above of recent release are freely downloadable from Microsoft website.

The dashboard can also be enabled in Windows Server Standard and Datacenter edition by enabling the Windows Server Essentials Experience server role. ↩

How to configure Windows as a NTP server & enable IOS NTP client

NTP allows to synchronize the clock of various devices to a common reference.

In this how-to, we will configure a Windows Server as a NTP server and a Cisco IOS-based router to act as a NTP client. We will also see how to configure the router so it can itself serve as server to other devices, thus acting as an NTP relay.

NTP how-to topology

Windows (NTP server)

Windows does not ship with any NTP server by default. In fact, Windows’ W32Time service implements SNTP instead, which is not compatible with NTP clients (see here).

Meinberg NTP is a commonly used alternative to get a proper NTP server on Windows, and is the one we will use in this how-to.

Before installing it, check that the following settings are correct:

The IP configuration (192.168.0.100 in my case)
Check the current time (08h15 in my case, but who cares?)

Once …

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How to create an Active Directory domain

Setting-up a basic Windows Active Directory Domains allowing to centrally manage users account can be done painlessly. This guide is mainly based on Peter Kim’s guide written for his book The Hacker Playbook

In this guide I use a minimal topology, with on one side a Windows server acting as the domain controller and on the other Windows client systems. This guide should work the same no matter the exact versions of the Windows server and clients you are using or if you are using a more complex and realistic topology.

Windows domain lab topology

Note

The Domain Controller must be a Windows Server edition, and for the clients to be able to join the domain they must be at least Windows Professional editions.

See how to choose a Windows edition.

Configure the network

Set IP addresses

First you need to set static IP addresses to each host.

The quickest way to access …

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How to configure Windows as a SCEP server & Cisco ASA enrollment

SCEP is a protocol supported by several manufacturers, including Microsoft and Cisco, and designed to make certificate issuance easier in particular in large-scale environments.

It proceeds in a few steps:

The SCEP server issues a one-time password (the “challenge password”), transmitted out-of-band to the client.
The client generates a key pair, and sends the certificate signing request to the SCEP server along with the one-time password.
The SCEP server validates the client certificate data (in this how-to the validation will be manual), signs it and makes the signed certificate available to the client.
The client regularly pull the SCEP server until its signed certificate becomes available. The client can then fetch the signed certificate and install it.

Here we will setup a Windows Server as SCEP server, and use a Cisco ASA as SCEP client.

SCEP how-to topology

The topology above mentions Windows 2016, but any other Windows server will do. This how-to …

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Where to find virtual machines and ISO files?

Free software

Virtual machines

Several websites offer a large selection of freely downloadable virtual machines with pre-configured free software, for instance:

TurnKey Linux.
Bitnami.

You can also check the marketplaces maintained by virtualization-related software, such as VMware and GNS3.

ISO files

Obviously the main place to get free software ISO files is from the projects website.

However, FrozenCow maintains a centralized list of direct links to a fair number of Linux and BSD installation ISO files.

Some projects host all previous versions of their system, but sometimes they are not easy to find. Search in priority on the master repository as these older versions may not be copied onto mirrors. Sometimes they are stored in a separate “archive” area. At last, WinWorld does a great job in collecting old systems installation medias, including discontinued Linux distributions.

If you are not sure which Linux or BSD system to choose, DistroWatch might …

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How to build a virtual pentest lab

Standalone virtual machines are both a cheaper and more practical solution to test systems as they doesn’t need to dedicate hardware and are easier to handle than physical installation (actions such as cloning, doing a snapshot or a rollback become trivial).

Network virtualization goes a step further and apply the same system to a whole network, including workstations, servers, and all networking devices such as switches, routers and firewalls. A virtual network can be of any size and topology, and can mimic any real-life situation such as Active Directory domains, remote-access or site-to-site VPNs or test protocols of every network plane.

Such virtual network can be either fully isolated or have one or several link to physical devices and networks, its all up to you to decide.

Hardware

Prerequisites

The goal of a virtual lab is to be able to quickly setup the environment which will allow you to …

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