Windows Server - extremely powerful, but extremely complex
Updated February 19, 2020

Windows Server - extremely powerful, but extremely complex

Aaron Pinsker | TrustRadius Reviewer
Score 7 out of 10
Vetted Review
Verified User

Overall Satisfaction with Windows Server

Windows Server is being used across 3 clients that I manage. It is primarily being used as a Domain Controller (with Active Directory), DNS server and file server. In addition, some clients are using the Hyper-V functionality built directly into Windows Server to create a virtual domain controller. In the organization that I manage that are using Windows Server, All business computers are apart of the Domain created by Windows Server and users are authenticated against the Active Directory.

Windows Server is an extremely large and complex piece of software capable of a LOT of different functionality, some of it good and some of it bad, thus creating a truly comprehensive review is difficult. This review consists primarily of how it is used as a Domain Controller and file server within an organization.
  • Windows Server acting as a domain controller allows for very comprehensive management of computers and workstations across an organization, specifically when it comes to Active Directory and Group Policy.
  • Active Directory allows for comprehensive managements of users within a domain (or organizational unit). User groups can be created with different permissions for various network resources, and users can be added to multiple different groups. In addition, login scripts can be created that are linked to each user allowing for automatic mapping of network drives and printers (among other items) every time a user logs in. As such, with the correct login script, a new user can login for the first time and have access to all the necessary resources within an organization.
  • Once a domain is created, adding computers to it is quick and easy. Any computer that is a part of a domain can be logged in by any domain user. Removing a computer from a domain, via Active Directory, immediately revokes all domain users ability to login to that computer.
  • Group Policy, an integral part of Windows Server, is a vast and comprehensive tool to push out settings to domain computers and users. Settings can be anything from adding or removing mapped network drives, adding or removing printers, turning on and off specific Windows settings. Group Policy can be managed on both a computer basis and a user basis.
  • Windows Server's built-in file sharing capabilities allow it to be used as a powerful file server. Permissions for shared folders can be set on a per-user basis and/or via group membership. Using advanced sharing features, a file or folder can be shared via multiple names with different permissions for each shared name.
  • Windows Server includes a powerful DNS server that works in conjunction with the Domain Controller functionality. The DNS server supports forward and reverse zones as well as manually adding items into a DNS zone.
  • Hyper-V is included with Windows Server, providing a powerful and first-party way to create virtual machines.
  • Windows Server includes a built-in DHCP server that can be used in place of a standard network router.
  • Windows Server includes a built-in web server hosting functionality via IIS (Internet Information Services)
  • Windows Server is extremely complex, and while newer versions have eased the initial setup process, setting up a server is still a very time consuming and difficult task.
  • The complexity of Windows Server also makes troubleshooting any problems that arise extremely difficult, both in tracking down the actual issue and then resolving the issue. Often times a problem can manifest itself in more than one way, making searching for the specific problem also difficult.
  • Windows Server is also very expensive, with complex and confusing licensing terms. In fact, Microsoft provides a 32-page PDF guide on Windows Server licensing, which is in and of itself dense and confusing to follow. To make matters more complicated, there multiple different version of Windows Server itself - Nano, Essentials, Standard and Datacenter edition, and each edition has different licensing terms. Licensing terms include items such as the physical processor's cores of the server, how many users will be accessing the server (called a CAL - client access license), and a plethora of other items.
  • Microsoft's support for Windows Server can be extremely frustrating at times. While Microsoft hosts a very active user forum, Microsoft employees who frequent those forums often provide only stock answers to questions (without actually reading the details) or no answers at all. For more in-depth - phone support can be quite expensive.
  • Upgrading a Windows Server from one major version to another (i.e. 2012 to 2016) is a frustratingly complex and dangerous procedure, as many things can go wrong during the upgrading, essentially breaking the entire setup. In fact, Microsoft doesn't even suggest doing an in-place upgrade, but to perform a backup of the existing server, doing a clean install of the new version, and migrating the information from the older version to the new version. In general, it is not even recommended to upgrade from one version to another as the risk significantly outweigh the benefits.
  • Positive ROI - Once set up properly, Windows Server's ability to manage an organization's users and computer drastically reduces the amount of time necessary to set up a new computer or a new user.
  • Positive ROI - Windows Server has a very large feature set, which can result in finding an additional use for it that was not initially intended. Specifically, Hyper-V has allowed some of the organization I've managed to create a number of virtual machines that have saved a considerable amount of time and money put into setting up a new piece of hardware.
  • Negative ROI - the initial setup of Windows Server is long and complicated. If your organization does not need the capabilities of Active Directory and Group Policy, the initial setup costs may not be worth it.
  • Negative ROI - the maintenance cost of keeping Windows Server functioning properly can be high, especially if any unforeseen issues arise. Again, if your organization does not need the capabilities of Active Directory and Group Policy, the initial setup costs may not be worth it.
  • Negative ROI - for many of the features of Windows Server (DNS server, DHCP server, web server, file server, etc.), there are less expensive, easier to setup, and easier to manage alternatives, especially in the NAS space.
There are other options out there that can provide many of the same functionalities of Window Server. Specifically, Synology NAS servers, in conjunction with Synology's excellent DSM (DiskStation Manager) software include a number of features that Windows Server includes, but in an easier to set up and less complicated manner. Specifically, DSM includes its bread and butter file server capabilities, a powerful DHCP Server, DNS Server, web server functionality using Apache, LDAP directory service (similar to Active Directory, but not as powerful), and even additional functionality not found in Windows Server such as powerful VPN server that can provide PPTP, L2TP, or even OpenVPN services.

However, there isn't a single piece of software or hardware that provides the same level of functionality as Windows Server's Active Directory and Group Policy management tools.
Windows Server excels as a Domain Controller with its comprehensive set of tools to manage users and computers. There isn't another software package out there that has the capabilities Windows Server does when it comes to Active Directory and Group Policy. In addition, Windows Server has a massive tool set, thus increasing both its functionality and flexibility.

Unfortunately, the flexibility and comprehensiveness of Windows Server causes it to be overly complicated to set up and manage, especially for a small organization. In addition, for things such as a file server, there are other options out there that are easier to use and more affordable - specifically in the NAS (network attached storage) space where both Synology and QNAP have very attractive options.

Perhaps the most frustrating aspects of Windows Server are the unnecessarily complicated and confusing licensing terms Microsoft has put forth. Sadly, this is not unusual when it comes to Microsoft, as the licensing even for their consumer-oriented products is burdensome.

Evaluating Windows Server and Competitors

  • Product Features
  • Product Usability
  • Prior Experience with the Product
The single most important feature was Windows Server Domain Controller functionalities - specifically in regards to Active Directory and Group Policy. There simply isn't a better tool on the market for managing Windows-based user and computers. While a Linux server or a NAS server can be set up with an LDAP directory that can allow network users to log in to a computer connected to the LDAP directory, the functionality isn't even remotely as powerful as Active Directory. Login scripts can be used to replicate some functionality of Group Policy, but Group Policy is vastly more powerful and flexible than login scripts.
If the organization is small enough, and doesn't have positions that turn over regularly, the need for Active Directory is minimal, and is most likely overkill. The best option is to evaluate what your organization needs out of a server. If it is simply for hosting files that everyone can access, a high quality NAS is a better option.

Using Windows Server

There are simply too many different parts of Windows Server to make it a cohesive piece of software. While some of the newer features found in Windows Server 2012 and 2016 have nice UIs that are logically laid out, there are enough parts of the system that is still based on old code with clunky UIs and confusing options to make Windows Server a particularly user-friendly experience.
Do not like to use
Unnecessarily complex
Difficult to use
Slow to learn
Lots to learn