just to resolve this thread, I’ve heard back from Tech Support and it is a bug:
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I’m very sorry for the delay in replying – I was hoping to have something substantive to report before I got back in touch with you. This is a complicated issue, and I tested it on several machines with several different configurations. I am able to reproduce on a few different versions and operating systems, and am currently communicating with our development team about potential patches and workarounds.
We don’t have anything to offer in the way of solutions right now, though I will say that this sort feature is functioning as expected in the Windows version of EndNote X1, so if switching platforms is a possibility, I would recomment that.
Otherwise, as soon as I learn anything more, I will let you know immediately.
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cheers