Hi! I tried to upgrade to LTSB 2016 using setup.exe, but "Keep personal files and apps" was grayed out. Is there anything I can do? I just tried using UpDown8 to change edition to Enterprise, but it didn't seem to work. Do I need to reboot? Thanks! (running Win7 Pro x64) Edit: Nope. Just rebooted, and "Keep personal files and apps" is still grayed out.
What do you expect. You have a Windows Pro with apps and settings and want to upgrade to an LTSB 2016er that has no apps. Why should you be there with "App and keep settings" can set a hook.
Maybe first look what upgrading from your current win 7 enterprise offers to keep when you try to upgrade to 10 enterprise and if that offers to keep all you need, upgrade and next do the reg trick and try to in place upgrade to Enterprise 2016 LTSB.
first upgrade to win 10 pro keeping all your apps then use reg trick to upgrade win 10 pro to win enterprise ltsb only way that worked for me.
Just change the values here HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Windows NT\CurrentVersion EditionID ---> EnterpriseS ProductName ---> Windows 10 Enterprise 2015 LTSB Then launch the setup. Pretty easy