- I assume you get an error message or some kind? Without one it is impossible to tell.
- I would try with another file format (ZIP it?) and see if that makes any difference; exe sounds like malware to me. Not sure what the preferred distribution format on Windows is, ZIP, MSI?
- The built-in Hugo server is meant for development; it works fine in production, but we have deliberately labeled it as a dev server to prevent having to support it in production and adding production like features. Nginx or similar should run fine on Docker.