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Follow up here - I've been attempting to use the .dmg solution suggested to no avail of late. I have a small c++ unix exe that I've code signed and placed into a disk image. That image is then signed and notarized (successfully - no issues listed in the log). I can then staple a ticket to the dmg file and everything running codesign/xcrun stapler validation checks out fine. Downloading the dmg file from web hosting however results in failure to run the exe after opening it. This is a somewhat critical piece of infrastructure for us that our developers need to use on their machines to help them get set up. Does anyone have any ideas?