The solution from @Developer Tools Engineer, @robnapier and @stragerneds did not work for me. I'm still getting "Failed to gain authorization", even after adding the entitlement. I'm debugging a plain executable. codesign -dvvv --entitlements=- /Users/ccleve/.pgrx/16.0/pgrx-install/bin/psq``` l Executable=/Users/ccleve/.pgrx/16.0/pgrx-install/bin/psql Identifier=psql-55554944e8e26ef3f50637679e1c2d5ded7430a8 Format=Mach-O thin (arm64) CodeDirectory v=20400 size=6342 flags=0x2(adhoc) hashes=187+7 location=embedded Hash type=sha256 size=32 CandidateCDHash sha256=1b033acfe360f3efe957c00c5b0436bb2e686d61 CandidateCDHashFull sha256=1b033acfe360f3efe957c00c5b0436bb2e686d61c71347c05bc36fb2c653fae2 Hash choices=sha256 CMSDigest=1b033acfe360f3efe957c00c5b0436bb2e686d61c71347c05bc36fb2c653fae2 CMSDigestType=2 Launch Constraints: None CDHash=1b033acfe360f3efe957c00c5b0436bb2e686d61 Signature=adhoc Info.plist=not bound TeamIdentifier=not set Sealed Resources=none Internal requirements count=0 size=12 [Dict] [Key] com.apple.security.get-task-allow [Value] [Bool] true (Not sure how to get the above output to format correctly.)