A few ideas: 1. confirm the checks are enabled: spctl --status 2. Make sure your terminal/shell/etc aren't already exempted System Preferences > Security

A few ideas: 1. confirm the checks are enabled: spctl --status 2. Make sure your terminal/shell/etc aren't already exempted System Preferences > Security & Privacy > Developer Tools. 3. If you already ran something that could generate a check in the last minute, the connection is still open. Most of the overhead people are recording is negotiation/handshake. If you're fairly close to the server, it seems plausible your observed time could be enough for the communication minus the negotiation. You can open Console.app and search `process:syspolicyd` in the device log to see the entries for the negotiation; wait for it to terminate. 4. Try removing and re-creating a new file as in the test you did before and check it a little more directly: spctl --assess -v --ignore-cache --no-cache /tmp/test.sh If it's working, you should see a log entry with the text "summary for task success" in it with a detailed breakdown of the request (times taken per phase, bytes sent/received, etc).