I'm probably not going to be suggesting anything very useful, but my question is, how does a user "upgrade" to a Windows 10 version that is not longer current? The only way I would know would be, on an enterprise network.
The current Windows 10 version is 20H2, which would be, in the old numbering scheme, 2009 or 2010. (I guess Microsoft determined that their original version numbers were too confusing, so now they seem to be called yyH1 and yyH2.)
To answer Pete's suggestion, it seems that even previously, this user must have been using a GL version of QB64 .exe files, or he would have needed to install his own QB64?
If the user is on an enterprise network, no telling what that network does, with "unknown" .exe files. In my case, on my work PC that is, the network always blocks execution of the program, until the user confirms he really wants to run that .exe file. Subsequently, the file will run as always.
I don't know of any incompatibility of QB64 GL executable files, among Windows 10 variants, but others might know better.
Edit: When I install a new QB64 development build, I do recompile the programs I need at the time. I only do this because I wipe clean the QB64 folder, which is where the previous QB64 files were stored. However, I've never needed to do this recompilation with Windows version updates.