Thanks for the suggestion. I was able to extract libui.dylib by running bundle install with the following configuration: cat ~/code/ruby/pathos_macos/.bundle/config --- BUNDLE_PATH: vendor/ BUNDLE_WITHOUT: development:test This created vendor/ruby/3.3.0/gems/libui-0.1.2-arm64-darwin/vendor/libui.dylib, which I ditto'd over to ~/Desktop/distribution/PATHmanager.app/Contents/Frameworks/libui.dylib I bumped version (as described previously) and ran my codesigning script which signs in the following order (under /Users/chip/Desktop/distribution/PATHmanager.app/): Contents/Frameworks/libui.dylib Contents/MacOS/PATHmanager PATHmanager.app directory After uploading the .pkg file using Transporter, I get this old error: Validation failed (409) App sandbox not enabled. The following executables must include the com.apple.security.app-sandbox entitlement with a Boolean value of true in the entitlements property list: [( com.chipcastle.pathmanager.pkg/Payload/PATHmanager.app/Contents/MacOS/PATHmanager )] Refer
Topic:
Code Signing
SubTopic:
General