I ran the WebUpdate_x64.exe installer as instructed. I then ran WUpdate_SSL.exe that was installed into \program files\WebUpdatex64\.

It didnt work. Then I noticed that the zip had 2 installers. When I ran the one in the subfolder, it worked as noted below.

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However, there remains some mystery here... Other than including the more recently compiled wupdate_ssl.sbp, what was different?

There's no way to compare the wupdate_ssl.sbp you provided to the one I have without opening them both and eyeballing each line to see what's different.

Can you clarify the difference between the wupdate_ssl.sbp in my dist/1033 folder as compared to the wupdate_ssl.sbp in the zip you provided?

Likewise - what change is necessary to make wucheck_ssl work?