Am working on upgrading thousands of Windows Server 2008 R2 to Internet Explorer 11. I am still deliberating on the best approach to this, any advice?
Uninstall the web browser from the server would be my advice. Shouldn’t be any reason to have IE on a server, let alone thousands of them. That’s Microsoft’s advice as well.
Though browsing from a server is ill -advised by todays risk standards, mainly because admins doing general workstation like browsing from a server (baaaad admins), it’s still a thing.
Especially if one is troubleshooting a server (while physically in a datacenter, not near any workstation and can’t use my phone due to no cell connection) and one needs to check TechNet/MSDN for some error message to quick-fix thing either manually, or when the help files provide you a link to click on. Otherwise, one has to run back and forth to a location with a workstation or cell connection to do the search, run back into the datacenter to continue - then rinse and repeat.
Heck there is even a browser control (Link to Web Address) that can be leveraged, natively via MMC.exe snapin that can be used to hit the web (well you have to set it for a specific address when you add it - but one can just give it the Bing, Google, DuckDuckGo address as well - but you can add as many of these links as you wish), even if you did remove the full browser. I have not tested if you remove the full browser, if the snapin will continue to work, but technically it should since it is separate. So, unless one can remove the browser and that browser snapin, one can still browse from the server via one or the other. Caveat, there is not updating or changing that snapin. It is what it is. Basic browse works in to for TechNet, MSDN and the like, but much of the rest of the web (active content stuff) will fail to function as expected.
So, you should not really need a browser on a server as suggested, relative to all the risk regarding it, but you can use the MMC to do limited browsing to say TN/MSDN/Docs.microsoft.com, but only you can decided what is or is not an acceptable risk to you.
Even though MS recommends this, they always include the browser in the OS. IMHO, if they recommend removing the browser, then it should never be there, by default at all and yes, WS2019 still has the full browser on it by default. 8^}. Well, not on Server Core in any version, which is where MS wants you to be for all supported role, and using PowerShell for all management or Windows Admin Center from your admin workstation, vs RDP.