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Old 10-24-2017, 05:18 PM   #3
Joe Miller
Human being with feelings
 
Join Date: May 2014
Location: Toronto
Posts: 35
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Try this. Grab the latest Reaper installer and double click the DMG. Drag the Reaper64.app across to your Applications folder, and without doing anything else on the Mac, open Reaper. Once it is open right click on the Reaper dock icon and say keep in dock. After Reaper is closed, it should remain in the dock without a question mark, even after reboot.

This problem of the question mark is caused by a security feature in MacOS called randomization, where it relocates the true location of executable apps in the Applications folder each time they are run, to protect against certain types of malware. The trouble is that it adds an application dragged from a DMG to MacOS database of apps to randomize only on the very first run right after you first dragged the app from the DMG. If you do anything else after that first drag, it forgets about Reaper and you end up with a question mark.

So in a nutshell, you have to mount Reaper's installer DMG, drag the app to Applications, and before running anything else, open the new Reaper app straight away, otherwise it will not pick up and remember Reaper for your dock icon.
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