I am aware of both this and this questions.
Which unfortunately didn\'t quite answer what I\'d like to know:
The answers in the above questions sugg
See Installer Detection, it lists what is checked to decide whether an executable is an installer.
"This program might not have..." is a product of "Program Compatibility Assitant", and is documented in the Application Compatibility: Program Compatibility Assistant (PCA) topic. According to the document the reinstall option applies XPSP2 compatibility mode.