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Replied In Gatekeeper rejects Non-sandboxed app with embedded command line tool

What setup are you using for that? Macbook M1 Pro, macOS 12.0, Parallels 17.1.0

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Replied In Gatekeeper rejects Non-sandboxed app with embedded command line tool

Yeah, that is weird. Were you testing on a fresh machine in each case? Yes, pretty much as you described it in your guide. Mac OS 12.0 virtual machine on arm64. I would test both builds on the same VM, Intel through Rosetta, but yielding different results. Other users running Intel on bare metal reported the same issue on the same Intel build though.

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Replied In Gatekeeper rejects Non-sandboxed app with embedded command line tool

Why are you signing with those entitlements? Specifically, com.apple.security.cs.disable-library-validation is only necessary if your app loads plug-ins from other third-party developers and, as noted in the docs, setting it can make it harder to pass Gatekeeper. Removing that entitlement solved my issue. Thanks for the help. It does make me wonder why gatekeeper behavior is different on M1 vs Intel though.