I didn't think of that. That would make future things easier or at least consistent. I recompiled WUPDATE_SLL and used my batch file to sign it. In the Redist directory.

My comment was more of a thought on why it didn't work in the first place. The only difference I can see is that the original was signed with both sha1 and sha256.
Or (I just noticed this) can it be that the certificate expired in 2021?

Thanks for all the help (and showing me that without including files to install some pretty cool utilities can be created with Setup Builder).