Starting in MacOS Sierra, I've started to get this popup periodically from XCode, even after pressing 'Always Allow'.
I've tried deleting the "com.apple.dt.XcodeDeviceMonitor" item in Keychain. This regenerates the key, but doesn't fix the issue.
It's an open discussion topic on the Apple forums, but no one seems to have a solution.
Posting this solution for Xcode 8 because no one else has:
That finally fixes it.
open [keychain access] > type "xcode" in the search area > double click [com.apple.dt.XcodeDeviceMonitor] > click [access control] > select the first option [allow all applications to access this item]
Don't forget to click Save Changes!
hope it helps.
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