Sorry! It is NOT that I refuse to help you. It is mostly I don’t know how… I asked for screenshots (a normal function of Windows, which I assumed you would know how to grab). I asked for the Debug Info (I told you what menu to go into to get it). You provided neither. Also, I thought telling you that NOTHING showed in " -> Configuration" was self evident and DIDN’T need a screen snapshot? The screenshot would have confirmed: 1) that there really was “nothing” there (maybe you and I have a different definition of “nothing”), 2) whether you had really selected “user scripts” or had selected “machine scripts”, and 3) that you were willing to follow instructions to try to get help. I’m happy to announce I’ve fixed it!!! Don’t ask me how but my WHOLE NP++ setup was weird!!! It seemed half in Program Files and half in AppData. That’s not weird. That’s how Notepad++ and PythonScript are intentionally set up. The FAQ footnote that I’ve begged you to read explains why there are the two different script locations. In fiddling around I copied the PythonScript directory from Program Files into AppData and TaDa! Everything fell into place… EVERYTHING WORKED like clockwork! You thus copied way too much. You could have copied just the scripts. Or you could have just clicked the “machine scripts” button in the dialog, like I told you to, and not had to copy any files. THANK YOU for your responses and help. Glad you’ve got it working.

I have checked out the https://github.com/donho/xmlSigner project and it is what I needed. I have used that project to correctly pass the XML signing test. I have opened some issues with that project. Here is a quick summary of how the update process works. The wingup code first queries a website to determine if an update is required and the returned XML provides information to be used later. None of the information in the XML is used if it doesn’t pass the XML security check. After passing the security check the code looks for the update status and download location, assuming an update is required. After prompting the user to download the update and finishing the download, it checks the code signing of the installer. Assuming that the code signing is valid and the correct certificate, it starts the install. I will try to document all the customizations to the code from Notepad++, wingup and xmlSigner to make it work in my project so that future users have a place to start, but that will be after I am sure its all working correctly with the new security updates. Thank you @xomx for pointing me in the right direction.