Why the Windows Server Essentials role could benefit larger organizations

Organizations may look to use an Essentials server, which makes Windows Server 2012 R2 function like Microsoft's small business offerings.

Small Business Server and its follow-on product, Windows Server Essentials, were options for tiny organizations that wanted a bunch of enterprise-style features and capabilities bundled up into one package. Until now, that package required everything be installed on a single, dedicated server that was not meant to integrate into an existing larger organization.

Now businesses can install the Windows Server Essentials Experience as a role within a standard SKU of Windows Server 2012 R2.

Why would an organization want to do this? The Windows Server Essentials role has some interesting features and end-user experiences that typically are not found in enterprise-style software. While there are more expensive packages like System Center, Forefront UAG and custom portals that will give you similar features, some folks would simply like to stick a box in the corner of their data center, install the Essentials role and have those features light up. After all, there is something to be said for simplicity.

The Essentials role includes a couple of compelling features:

Client backup: The Essentials role makes available a little connector that installs on network workstations that essentially (get it?) interfaces with the Windows Backup program and streams an image-based backup of the workstation to the Essentials server or the machine hosting the Essentials role. This works even with servers, as an Essentials server sees all machines that are not it as potential clients to manage. This can be a handy way to back up even a sensitive subset of your machines, such as VIP employees, kiosks that might need regular rebuilding, branch office servers and so on.

Remote Web Access: This is a nice Web portal users can log into over HTTPS to access files and file shares on the network, log into assigned computers remotely over Remote Desktop Protocol, and access other links hosted within the portal. While more expensive and complex products often allow this sort of portal experience, the Essentials portal marries file management and remote desktop access into an attractive and simple option.

Cloud integration: If you have a small business or even a medium-sized organization that uses Office 365, the Essentials user management console features decent integration with the cloud service that lets you manage users, synchronize passwords, and provision and manage email addresses for Exchange Online. You can also use the Windows Azure Backup service to back up the data stored on your Essentials server, although this is probably a limited utility in a larger organization in which data is typically stored on a storage area network or network-attached storage, instead of on the machine hosting the Essentials role itself.

Potential roadblocks to running the Windows Server Essentials role

There are considerations to note about installing the Essentials role within your network on machines running Windows Server 2012 R2.

There is an important distinction between licensing or purchasing the Windows Server Essentials SKU and running the Essentials Role. Licensing Windows Server Essentials comes with up to 25 client access licenses (CALs). In contrast, you'll need CALs for any clients that touch services running on the server(s) on which you installed the Essentials role as part of the regular Windows Server 2012 R2 full packaged product. This is particularly important with regard to the Remote Web Access feature, which uses Remote Desktop Gateway.

Unless you have a Remote Desktop Services CAL, which is different than a standard Windows desktop CAL, you are not properly licensed to use the feature if it's installed via the Windows Server role. As usual, Microsoft's quirky and confusing licensing model muddies what might be a decent value proposition for many organizations.

In addition, there is a bug that prevents you from deploying the Office 365 integration components of the Essentials role into an environment with more than one domain controller -- a deployment scenario that's almost universal in large organizations. Microsoft has confirmed this bug, and it will be fixed in a later update or feature pack; however, if you have more than one domain controller in your domain, the Office 365 management features are not for you at this time.

There also are some technical limitations. You can only install the Essentials role into a single domain and you cannot -- under any circumstances -- have a read-only domain controller in that domain.

Still, the Essentials role on Windows Server 2012 R2 is worth a look if any of the unique features may have a place in your organization. It really is a matter of clicking a couple of checkboxes, rebooting and then lighting up those capabilities.

About the author:
Jonathan Hassell is an author, consultant and speaker on a variety of IT topics. His published works include RADIUSHardening WindowsUsing Microsoft Windows Small Business Server 2003 and Learning Windows Server 2003. Jonathan also speaks worldwide on topics ranging from networking and security to Windows administration. He is president of 82 Ventures LLC, based in North Carolina, and is currently an editor for Apress Media LLC, a publishing company that specializes in books for programmers and IT professionals.

This was first published in January 2014

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