We think our compatibility issue can be handled, so this problem has probably become academic, but a simple reproducible case is listed at the end. You’re talking about running the program from the Unix shell that’s running in Terminal, right? Why is the tool bundled? Correct - that is its only mode of operation. It is a structured collection of nearly a thousand filesystem objects that includes a JRE. Finally, how are you testing this? My general advice is that you run each test on a fresh (virtual) machine Unfortunately, we don't yet have access to VMs. (It would be very useful for Apple to add a test VM creation CLI to the developer toolkit now that the core functionality is built into macOS.) Repro case: Download a JRE tgz, e.g. https://adoptium.net/temurin/releases/?os=mac&version=21&package=jre&arch=aarch64 Re-archive as non-suffixed zip: tar -xzf OpenJDK21U-jre_aarch64_mac_hotspot_21.0.7_6.tar.gz && mv jdk-21.0.7+6-jre jdkjre && zip -qr jdkjre.zip jdkjre Quarantine the zip Failure as non-suffixed bundle: unzip -q jdkjre.zip && jdkjre/Contents/Home/bin/java --version Success as suffixed bundle: mv jdkjre jdk.jre && jdk.jre/Contents/Home/bin/java --version