Installing Windows Server Essentials Experience On Windows Server 2019 / 2022 / 2025

2018    Posted Posted by Mike     Comments 412 comments     Modified Last updated: July 7, 2024
Oct
4

As mentioned in my previous post, Microsoft has completely removed the Windows Server Essentials Experience (WSEE) server role from Windows Server 2019. However, since the entire Windows Server Essentials Experience is basically just an elaborate .NET application that is installed on top of the Windows Server operating system (and not some tightly integrated system component of the OS itself), it can quite readily be installed onto Windows Server 2019 and beyond.

Background Information And Proof Of Concept

Windows Server 2016 is built upon the Windows 10 version 1607 platform, and so it stands to reason that any .NET application that runs on it “should” run equally well on Windows Server 2019 (which is built upon the similar, but newer, Windows 10 version 1809 platform). This certainly holds true for the Windows Server Essentials Experience .NET application seeing as it runs exactly the same under Windows Server 2019 (and beyond) as it does under Windows Server 2016.

To install the Windows Server Essentials Experience on Windows Server 2019 / 2022 / 2025, all that needs to be done is for you to copy its required files and registry entries from Windows Server 2016 over to Windows Server 2019 / 2022 / 2025, add its prerequisite server roles and features, create its required services, and then complete its setup process by running the Configure Windows Server Essentials wizard. As you can see from the following screenshots, everything works quite nicely once it has been properly installed and configured.

The “Configure Windows Server Essentials” wizard works perfectly when performing the initial configuration of Windows Server Essentials on Windows Server 2019 / 2022 / 2025

The configuration wizard even works when Windows Server 2019 / 2022 / 2025 is joined to an existing domain (i.e. when it is running as a member server, rather than acting as the primary domain controller)…

After Windows Server Essentials has been successfully configured you can then simply open up the server Dashboard (as usual) and start enjoying all the features of the Windows Server Essentials Experience server role on Windows Server 2019 / 2022 / 2025.

Client Connect and Client Backup works…

Server Backup works…

Storage (Server Folders, Storage Spaces, etc.) works…

Anywhere Access / Remote Web Access works…

Add-ins work (including our very own WSE RemoteApp and WSE WorkFolders)…

Everything works exactly as it does under Windows Server 2016!

Obviously, doing this will never be sanctioned nor supported by Microsoft, and so you may be asking yourself why not just stick with using Windows Server 2016 since it is fully supported by Microsoft until January 12, 2027? While you certainly can (and should) do that, probably the best answer I can give you is… Because you can! That being said, it’s worth mentioning that since Windows Server 2019 and Windows Server 2022 have now reached general availability (A.K.A. RTM), there will most likely come a time in the not too distant future, when Microsoft will stop selling Windows Server 2016 licenses. Being able to do this will allow those folks who wish to set up a newer server with the Windows Server Essentials Experience to continue to be able to do so once those Windows Server 2016 licenses become hard (if not impossible) to find. It will also allow those folks who would like to enjoy the added security, and other benefits, that come along with using Windows Server 2019 / 2022 / 2025 to be able to continue using the Windows Server Essentials Experience on their Small Office / Home Office (SOHO) servers.

How To Get Started

The installation can be performed by grabbing the install.wim file from a Windows Server 2016 Essentials installation disc (or from a mounted ISO image), and then mounting and extracting it using the Deployment Image Servicing and Management (DISM) command-line tool by following the steps Microsoft provides here. After doing that, grab all of the required Windows Server Essentials files (including the ones in the GAC), extract the required registry entries, and copy them over to Windows Server 2019 / 2022 / 2025. Then use Server Manager to add the prerequisite server roles and features, create the required services, and use PowerShell to start the initial configuration of Windows Server Essentials.

ALTERNATIVELY, if you already own (or newly purchase) a license for one of our software products, then you can contact us with the User Name from the license of your purchased software product, and we’ll be more than happy to share (at no additional charge) a password that you can enter below in order to download the WSEE Installer package (i.e. MSI file) that we’ve built for our own use in installing (and uninstalling) the Windows Server Essentials Experience onto Windows Server 2019 / 2022 / 2025.

The WSEE Installer makes installing the Windows Server Essentials Experience (WSEE) from Windows Server 2016 on Windows Server 2019 / 2022 / 2025 super simple! You just install Windows Server 2019 / 2022 / 2025 Standard or Datacenter, with the Desktop Experience GUI in the language of your choice, onto your server and then run the WSEE Installer package’s MSI file directly from the server desktop (the Windows Server 2019 Essentials SKU can be used, but is NOT recommended!). The WSEE Installer will handle installing all required files, registry entries, prerequisite server roles/features, services, permissions, etc., and then launch the “Configure Windows Server Essentials” wizard to walk you through configuring Windows Server Essentials on your server (as shown in the images above). The WSEE Installer will even monitor your installation and alert you whenever updates become available (via a health alert that gets displayed within the server Dashboard, and optionally emailed to you via the Windows Server Essentials server’s built-in Health Report Add-In feature). Available updates can then be, quickly and easily, installed via our WSEE Updater program. 😎

INFO: The WSEE Installer does so much more for you than can ever be achieved with a manual installation of WSEE, that we no longer recommend folks attempt to install WSEE manually. Using the WSEE Installer will net you a MUCH MORE complete / proper / secure (and hassle free) installation of WSEE (including support for in place upgrades from prior releases of Windows Server and alerts whenever feature and/or security updates become available; along with a simple/easy means of installing those updates via our WSEE Updater program), and so we now STRONGLY RECOMMEND that everyone use it instead.

NOTE: We DO NOT SELL the WSEE Installer (seeing as the “Essentials bits” it installs are not ours to sell, and since we DO NOT officially provide support for it). It is ONLY made available, at no additional charge, as a convenience (and thank you) to purchasers of our software products.

NOTE: You may use the WSEE Installer to install WSEE on a single server only (i.e. it’s one WSEE installation per purchased software product). If you wish to use the WSEE Installer to install WSEE on multiple servers (for testing or migration purposes, for other clients, family members, friends, etc.), then each server installation MUST be associated with a unique licensee (i.e. User Name) from one of our software products. For additional information see the WSEE Installer policy.

NOTE: The WSEE Installer was built using Windows Server 2016 Standard OS Build 14393.4169 as its source. It is available in Dutch, English, French, German, Italian, Spanish, etc. Be sure to specify your language preference when requesting download access. The language of the WSEE Installer that you use should match the language of the installation media used to install Windows Server onto your server (i.e. don’t mismatch the languages).

💡 UPDATE (7/6/2024): The WSEE Installer Version 10.0.14393.4169 (Revision 27) is available for download (by entering a password below). Click here to see what’s new!

😎 INFO: If you’ve installed WSEE on your server via any prior version of the WSEE Installer, use the WSEE Updater to bring your existing WSEE installation up-to-date.

INFO: Our WSE RemoteApp and WSE WorkFolders products run splendidly on Windows Server 2019 / 2022 / 2025 with WSEE installed. Your existing, or newly purchased, license covers the use of the product on Windows Server 2016, 2019, 2022, or 2025.

Suggestions, Limitations, and Known Issues

While in-place upgrades and domain migrations from earlier versions of Windows Server (Essentials) work just fine, we highly recommend that you always start off with a brand new/clean (i.e. straight out-of-the-box) installation of Windows Server 2019 / 2022 / 2025 Standard or Datacenter (with the Desktop Experience GUI in the language of your choice), that has all of the latest Windows Updates installed. The server may be natively joined to a domain if desired, but make sure that no other server roles, features or applications have been installed.

You should NOT attempt to install the Windows Server Essentials Experience on the Windows Server 2019 Essentials SKU (which, despite its name, has absolutely nothing whatsoever to do with “Essentials” as we currently know it). This is because Microsoft has removed all of the Remote Desktop Services roles from the SKU, and so the required Remote Desktop Gateway role will not be available for use by the Anywhere Access / Remote Web Access features of Windows Server Essentials. Save yourself the time and hassle, and just use Windows Server 2019 / 2022 / 2025 Standard or Datacenter instead (and don’t fret about silly CALs). If needed, you can convert the Windows Server 2019 Essentials SKU into Standard or Datacenter by running one of the DISM commands mentioned below…

NOTE: You can download an evaluation version of Windows Server 2019 (Standard or Datacenter), in ISO format, from the Microsoft Evaluation Center here. You can download an evaluation version of Windows Server 2022 (Standard or Datacenter), in ISO format, from the Microsoft Evaluation Center here. You can download an evaluation version of Windows Server 2025 (Standard or Datacenter), in ISO format, from the Microsoft Evaluation Center here.

INFO: You can evaluate the product for up to 180 days, and you can extend the trial period for another full 180 days (up to six times for a grand total of 3 years) by running the following command from an elevated command prompt:

slmgr -rearm

INFO: You can run one of the following commands, from an elevated command prompt, in order to convert the evaluation version into a regular retail version (Standard or Datacenter) using a purchased retail Product Key:

DISM /online /Set-edition:ServerStandard /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula

DISM /online /Set-edition:ServerDatacenter /ProductKey:XXXXX-XXXXX-XXXXX-XXXXX-XXXXX /AcceptEula

💡 HINT: You can use Windows Server 2019 / 2022 / 2025 for free by running one of the following commands, from an elevated command prompt, in order to convert the evaluation version into a volume-licensed version (Standard or Datacenter) using a Generic Volume License Key (GVLK) from Microsoft:

Windows Server 2019:

DISM /online /Set-edition:ServerStandard /ProductKey:N69G4-B89J2-4G8F4-WWYCC-J464C /AcceptEula

DISM /online /Set-edition:ServerDatacenter /ProductKey:WMDGN-G9PQG-XVVXX-R3X43-63DFG /AcceptEula

Windows Server 2022:

DISM /online /Set-edition:ServerStandard /ProductKey:VDYBN-27WPP-V4HQT-9VMD4-VMK7H /AcceptEula

DISM /online /Set-edition:ServerDatacenter /ProductKey:WX4NM-KYWYW-QJJR4-XV3QB-6VM33 /AcceptEula

Windows Server 2025:

DISM /online /Set-edition:ServerStandard /ProductKey:TVRH6-WHNXV-R9WG3-9XRFY-MY832 /AcceptEula

DISM /online /Set-edition:ServerDatacenter /ProductKey:D764K-2NDRG-47T6Q-P8T8W-YP6DF /AcceptEula

After doing that, you can then automate activation of the volume-licensed version using abbodi’s KMS_VL_ALL script that sets up a local KMS server emulator on the server. 😎

(8/25/2019): After configuring Windows Server Essentials, you may see a health alert stating that your “Active Directory domain names can’t be resolved“. If so, then change the adapter settings/options for the network connection on your Essentials server so that its preferred IPv4 DNS server address is set to the default 127.0.0.1 localhost/loopback address, and its alternate IPv4 DNS server address is set to the IP address of your network router (e.g. 192.168.1.1) or other DNS server (e.g. 8.8.8.8). You should also verify that the preferred IPv6 DNS server address is set to its default ::1 value.

NOTE: In addition, you should also change the adapter settings/options for the network connection on ALL of your client computers so that their preferred IPv4 DNS server address is set to the static IP address of your Essentials server, and their alternate IPv4 DNS server address is set to the IP address of your network router (e.g. 192.168.1.1) or other DNS server (e.g. 8.8.8.8). Doing so will allow the client-side Windows Server Essentials Connector software’s installer (which you can download from each of your client computers by browsing to http://<ServerName>/connect; where <ServerName> is the name of your Essentials server) to be able to successfully locate and connect the client computer to your Essentials server.

INFO: If the Windows Server Essentials Connector software (still) has trouble locating your Essentials server, then try adding the “SchUseStrongCrypto” and “SystemDefaultTlsVersions.NET Framework security settings to the Windows Registry of BOTH your server and ALL of your client computers, and then reboot them. The settings allow the older v2 and v4 versions of Microsoft’s .NET Framework packages (used in Windows Server Essentials) to be able to utilize newer/stronger TLS 1.2 SSL connections whenever the clients attempt to communicate with the server.

INFO: If you do not want to join your connected client computers to the Windows Server Essentials domain, then you can use Microsoft’s SkipDomainJoin connection method instead.

During (and after) the configuration of Anywhere Access / Remote Web Access, you may see a benign error about your firewall settings (e.g. “There is an error in your firewall settings – Your firewall may be blocking Anywhere Access to your server and the problem cannot be repaired automatically.“). You can safely ignore this error seeing as it is just a false-positive that is being caused by an issue where the localized names of the required firewall rules are not being properly read from their resource files.

NOTE: The accompanying health alert will automatically be disabled for you when using our WSEE Installer (but the error will still appear within the Configure/Repair Anywhere Access Wizard itself).

(3/8/2021): The Microsoft Online Integration Services (such as Office 365 and Azure Active Directory) will work as designed when WSEE has been installed using our WSEE Installer (Version 10.0.14393.4169 (Revision 3) or greater).

NOTE: The online integration services in Windows Server Essentials are NOT compatible with multi-factor authentication (MFA) being enabled on your Office 365 / Azure Active Directory user accounts. Therefore, you should make sure that MFA is disabled by signing in to the Microsoft 365 admin center, clicking on UsersActive users, clicking on your admin user, and then clicking on the Manage multifactor authentication link located on the Account tab.

Microsoft has also implemented something called security defaults in Azure Active Directory, and since enforcing the enabling of MFA on all of your user accounts (within 14 days) is part of this security feature, you will need to disable it as follows:

• Sign in to the Azure portal as an administrator.
• Browse to Manage Azure Active Directory → Properties.
• Select Manage security defaults.
• Set the Enable security defaults toggle to No.
• Select Save.

(3/15/2021): The Windows Server Essentials Best Practice Analyzer (BPA) tool works when WSEE has been installed using the WSEE Installer (Version 10.0.14393.4169 (Revision 4) or greater).

NOTE: To run the Windows Server Essentials Best Practice Analyzer (BPA) tool:

• Log on to the Essentials server as an administrator, and then open the Configure Windows Server Essentials wizard (click Start → type EssentialsRoleConfigWizard.exe).
• Close the configuration wizard after confirming that Windows Server Essentials has been successfully configured on the server.
• Open Server Manager, and then click the Windows Server Essentials Experience tab.
• In the details pane, scroll down to the BEST PRACTICES ANALYZER.
• If a filter is applied, click Clear All.
• Click TASKS, and then click Start BPA Scan.
• Review each BPA message, and follow the instructions to resolve issues, if necessary.
SEE: Rules used by the Windows Server Essentials Best Practices Analyzer (BPA) Tool

Closing Remarks

We’ve tested all of this quite extensively, and it consistently works great for us here. However, your results may vary. Please don’t blame us (nor Microsoft) if you can’t get it to work, or if something goes wrong on your server. None of this is officially supported by Microsoft (nor by us!), and so you should proceed at your own risk. You fully assume all risk, responsibility, and liability associated with the installation. And as always, make sure that you have a working backup of your server, and all of your data, before proceeding.

That being said, it works so well for us here, that we have now switched all of our SOHO servers over to running Windows Server 2019 / 2022 / 2025 with the Windows Server Essentials Experience installed.

That’s it! Enjoy using the Windows Server Essentials Experience on Windows Server 2019 / 2022 / 2025.

— MIKE (The Office Maven)



EDIT (6/26/2019): As the months keep flying on by, we’re finding that the longer we use the Windows Server Essentials Experience on Windows Server 2019, the more we’re coming to realize just how much better Windows Server 2019 is than Windows Server 2016. While the “Essentials” bits themselves are of course identical (seeing as they’re just being brought straight over, untouched, from 2016), they run MUCH BETTER under 2019. Windows Server 2019 is leaps-and-bounds faster than Windows Server 2016 is (it boots up faster, and everything, including the server Dashboard, etc., just runs faster/better under it). Lots of bugs that plague 2016 are fixed under 2019. Overall, we’re finding that using WSEE on 2019 is an all-around much better experience.

EDIT (9/1/2021): The Windows Server Essentials Experience also installs, and runs wonderfully, on Microsoft’s GA/RTM release of Windows Server 2022. Enjoy! 😎

EDIT (5/23/2024): The Windows Server Essentials Experience also installs, and runs wonderfully, on Microsoft’s GA/RTM release of Windows Server 2025 (i.e., the next version of Windows Server with the new Windows 11 style Graphical User Interface). Enjoy! 😎

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