Shortcut 'Run as Admin' setting not working, context menu 'Run as Admin' option works

[Marlo M]

I have a .exe that will only run using the 'Run as Admin' option in the context menu. This is true for either the .exe itself or the shortcut to it. In the properties for the short cut, I've given it the 'Run as Admin' permissions, running it will provide the same dialogue box asking for confirmation but the .exe will run with an error. Ultimately the question is this, what is the difference between running as administrator from the context menu and running as admin as defined in the properties?

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