Steps to be taken...


Forgive the newb question but I want to make sure I don’t make a mess of things inadvertently.

I have just completed installing Windows Server 2019 Standard and I have the WSEE file downloaded and ready to go.

Is there a particular set of steps one should take in a particular order?

For example: I have not yet connected my server to the internet (so no updates installed yet)… Should I do this first or go with the WSEE file first then updates?

I did a cursory search of your Q&A and didn’t see anything, though I may have missed it also.

Thanks in advance.


(P.S. I just yesterday decommissioned my WHS2011 box… So this is all new to me).

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Great Answer

Sounds like you’re on the right track…

Go ahead and enable the Internet connection on the server, install all of the latest Windows Updates on it, and then run the WSEE Installer.

Basically, you want to start off with a brand new/clean (i.e. straight out-of-the-box) Windows Server install as your base. Do NOT install any server roles, features, or applications on the server until after you’ve installed WSEE and have completed the “Configure Windows Server Essentials” wizard.

After doing that, you can run the “Windows Server Essentials Connector” software on your client PCs (by opening a web browser window on them and going to http://<YourServerName>/connect) in order to connect them to the server (for client backups, etc.). Since you’re a WHS 2011 user, you may not want your client PCs domain joined to your Essentials server, and in that case, you can simply use Microsoft’s “SkipDomainJoin” connection method in order to stop that from happening (and hence make them behave more like WHS 2011 did). For more info on that see:

Connect computers to a Windows Server Essentials server without joining the domain

Best of luck.

  • Fortium
    Well, everything seemed to go off flawlessly. No hiccups or problems that I am aware of. One somewhat frustrating question remains, and I know it’s simply my lack of familiarity with Windows Server 2019. I followed the steps you recommended… a fresh install of Server 2019 Standard. Then, before I fired up the WSEE installer, I updated the server as you recommended. Or did I? You see, I “updated” by going to windows update in the settings menu and smashing the button until everything was applied and nothing else remained. But upon further scrutiny, I realized that my fully updated Windows Server 2019 Standard install was still “version 1803”. Based on my knowledge of updating Windows 10 (which updated to 21H2 through the very same button gnashing procedure), then my server installation is “fully updated – to vintage 2018 standards”… LOL /sigh And now I’m trying to parse through just text wall after text wall of update jargon, armchair computer pundits, “containers”… (do you burp them?), Long Term Nausea-Channels, and a confusing mess half of which doesn’t seem to apply to my situation. Have they done away with *click this link to download an updater file that will efffortlessly take your 1803 install up to 21H2”? So, in short, I did run the WSEE installer and it worked great, but I can’t honestly say I did *the right kind* of updates beforehand. /grr
  • Mike
    Windows Server doesn’t work like the the consumer editions of Windows 10/11 do as far as Windows Updates go. Therefore the behavior that you’re seeing there is indeed correct (i.e. from what you’ve described, it’s working exactly as Microsoft has designed it to work).
  • Fortium
    I have read that others have begun upgrading their installs from Server 2019 to Server 2022. I foresee no urgent need for me to do the same. If and when I do wish to upgrade, would you recommend a clean bare metal install of 2022, port in the license, run windows updates, then reinstall WSEE. Of is there an more preferred approach? Once again, thanks for all you do. My experience with your software has been entirely positive and damn near effortless. Thank you again.
  • Mike
    While it’s always “recommended” to perform a brand new/clean install when moving up to a newer version of Windows Server, in-place upgrades from 2019 to 2022 (when WSEE has been installed via the WSEE Installer) tend to work just fine. The only thing to be aware of is that Microsoft will forcefully remove all of the WSEE components during the in-place upgrade process, leaving you with an orphaned WSEE (Installer) instance. To work around that issue, I’ve built a “WSEE Zapper” program that will quickly remove the orphaned instance, allowing you to be able to run the WSEE Installer once again. The WSEE Installer will then recognize that WSEE had been previously installed, and it will simply reconfigure the server accordingly (as opposed to starting over completely from scratch again).
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