Recently, we have been installing Windows Server Essentials R2 on most of the new servers we install. I feel like it is a great operating system, but I kept running into issues when I was going through the setup of the server. Here is a brief rundown of the issue and the resolution we came up with.
Problem: I would install Windows Server Essentials R2 and create the default administrator account. Once I logged into the default administrator account the “Configure Windows Server Essentials” dialog would come up. I entered the information and then clicked, “Configure”. However, every time the setup wizard would get to one or two percent and it would give the following error message: “An error occurred while configuring Windows Server Essentials. Please try again. “ 
I would hit the “Retry” button but it would still fail. I then rebooted the server but when I logged into the administrator account, the setup wizard wouldn’t let me change the information I entered. I then had to reboot the server and reinstall the operating system. As you can see it was quite frustrating reinstalling the operating system again and again.
A couple of possible scenarios came into mind. We thought, since there was already a domain controller on the network that maybe there was an interference. So we put the server on its own network but it didn’t help. We then thought maybe it was because their were some missing drivers. We installed the drivers but it didn’t help. We were pretty much at our wits ends. We thought it could be possible that the server name or account information was giving the setup wizard some issues.
Resolution: After much troubleshooting and trial and error, we isolated the issue. During the setup wizard I made the administrator account user.admin (example). When I clicked, configure, it instantly failed the setup like before. I reloaded the server and this time chose a username with out admin or administrator apart of it. This time it went through without any hiccups! Apparently, when going through the setup wizard, you can’t have admin or administrator in the username. I am not sure why this is. It could be a safety precaution since there is already an administrator account by default. This seems to be the resolution for this error that I was receiving.
I hope this helps you out! It would be great if you left a comment, if you ran into this issue as well. Like us on Facebook!
This was posted by techspeeder.
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Instead of re-installing the OS, you can simply use the Remove Server Roles dialogs to remove the Server Essentials, then reboot
Hello Chris, You are correct if you are using Windows Server 2012/R2. However, with the standalone Windows Server Essentials R2 software your only option is to reinstall the operating system.
Regarding doing this with the standalone Windows Server Essentials R2 software you can run an elevated powershell prompt and type in: Uninstall-WindowsFeature ServerEssentialsRole – I had to run this twice with a reboot in between and then I started and completed the wizard from scratch (with a new username). It should be noted on my first attempt to use the wizard with the offending username I only got as far as the first automatic reboot which as far as I could tell just renamed the computer and did nothing else before presenting me with the error.
Agreed, no need to reinstall. In 2016 Essentials start PowerShell and type:
Remove-WssConfigurationData
Uninstall-WindowsFeature ServerEssentialsRole
then reboot. Configure Windows Server Essentials wizard will now start from scratch. Remember not to use “admin” word in network administrator username this time 😉
Was trying to set up Windows Server 2012 R2 Essentials on my Intel NUC (model NUC5i7RYH) and was getting the same repeated error message/screen shown above. I tried debugging using a lot of other references I found online but was stuck with the same error. Came across your post above and gave it a try since my server administrator user name was “ABCDadmin”. I quickly reinstalled the OS and changed it to something without *admin* in it. It worked like a champ the first time!
Just to confirm, I tried it again on an identical set up of hardware with the original “ABCDadmin” in the name and it failed there as well. Repeating the process with the non-“admin” characters in the user name worked again.
Thanks VERY MUCH for posting this bit of advice! I confirm your solution!
Thanks for taking the time to share your experience with me! It helps me as well as other readers.
Incredibly, this is still a problem in Windows Server 2016 Essentials.
If you enter a server administrator username containing “Admin”, the Essentials configuration fails with that vague error message, and no way to fix it but to reinstall from scratch.
I stuck at 95%, after doing everything I found that regional zone was misconfigured. I set up the righ one, retried and worked!!!!!!!!!!!!!
WSE2016. Endlessly stuck at 16%. It was failing at user creation (creating the “network administrator” account) (don’t have the log files handy to paste details here). The name did NOT have admin in it, etc. The problem was SPECIAL CHARS IN THE PASSWORD. So keeping the password alphanumeric worked, then changed it later.
I have just managed to fix this issue without reinstalling the OS:
1. Cancel the Wizard when it appears
2. Stop the Windows Server Essentials Management Service (no need to Disable)
3. Run the Wizard again manually by going to Run and entering:
C:\Windows\explorer.exe “C:\Windows\System32\EssentialsRoleConfigWizard.exe”
4. The Wizard will fail again – start the Windows Server Essentials Management Service
5. Now click Retry and the Wizard should complete
I have only tried this once and I had actually manually installed Active Directory roles by this point, so not sure if this is a pre-requisite, but (somewhat unbelievably!) it worked and the Wizard completed successfully.
EDIT: I had also given ServerAdmin$ Log as service rights by this point as well
(https://blogs.technet.microsoft.com/sbs/2013/12/04/you-may-be-unable-to-run-post-deployment-configuration-wizard-after-you-install-the-windows-server-essentials-experience-role/)
Thank you guys very much. the powershell commands posted by Raul as well as not using admin in the network admin name and keeping the password to Alpha Numeric solved my issue.
Thanks again.
Thank you for above post. Changing the name to exclude keyword “admin” helped to resolve the issue of configuration.