SmartScreen on Windows displays a warning when I open on some of the binaries that I release but not all of them. Do I need to sign all the installers? Is there a cheap way to do that? Recommendations on which certificate issuer to use would be highly appreciated if that is the way to solve the problem.
You can not sign an application to bypass smart-screen. Smart-screen gives every exe file it comes across a "reputation". The more people open an exe file and trust it, the better its reputation becomes. There is no way to bypass it.