Mac Developer: Technical Note TN2206: OS X Code Signing In Depth
Technical Note TN2206: OS X Code Signing In Depth: "Checking Gatekeeper Conformance
To test Gatekeeper conformance, you must use OS X 10.9.5 or later. Follow these steps:
Package your program the way you ship it, such as in a disk image.
Download it from its website, or mail it to yourself, or send it to yourself using AirDrop or Message. This will quarantine the downloaded copy. This is necessary to trigger the Gatekeeper check as Gatekeeper only checks quarantined files the first time they're opened.
Hint: keep the downloaded .dmg around; it will stay quarantined and you can use it again and again to test.
Drag-install your app and launch it.
Observe the results.
Hint: Don't launch from inside the .dmg."
A quick guide to testing Gatekeeper conformance under 10.9.5