Turns out the problem is "preenc". Try setting it to "encounter" and it'll work just fine.
Relevant snippets from
another thread that clued me in to this possibility:
Quote:
Phlagm:
Has anyone had success with using preenc in a condition, or do you know where it may have been used? I can get firstenc and encounter to launch the quest I'm trying to launch, but preenc does nothing.
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Quote:
Fingers:
The pre-encounter condition is used in mantle_gar and mantle_url to set that race to be your enemy if you arrive without the mantle and have made friends with them earlier.
The preenc is triggered just before the radar screen would pop up. The radar would not pop up if they were friendly, that's why this feature was added. It may not be possible to use preenc to pop up a quest window as it's only intended to make (invisible) preparations before the actual encounter.
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I tested your quest repeatedly, but with "FLAG always" and "CONDITION TYPE encounter" and it worked every time.