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[Iecerint]

 I suspect it may have something to do with my abilities?

Team: Infiltrator -- Kaidan -- EDI.  Killed Kai Leng second-to-last both times, leaving one Phantom afterward.  Pressing  L3 gives a "Defeat Kai Leng" objective and puts it just behind the Illusive Man's Chair.

I tried quicksaving (permitted) and reloading, which leads the fight to play out from the beginning, except that Kai Leng's support does not spawn (I presume that they're marked as "defeated") and Kai Leng spends an unusually large amount of time "re-charging" his shields (though he does stop after 60-90 seconds or so).  Killing him against leaves the game to play on without triggering the Kai Leng defeat cutscene.

Just reporting a bug.

[Iecerint]

Bonus Power: Energy Shield

It registered the win normally on the third win, but it happened twice consecutively before that.

[Nimpe]

Happened to me once. Reloaded and killed him again and it worked. Seems to be a random error. I killed him on two other playthroughs with no problem.