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Actually, I've had something like that happen to me.
Traveled to Waukeen's Promenade to meet with the leader of a different Shadow Guild (for the thief stronghold), they show up.
At the same time, I'm ambushed by the Kensai/Mage who comes after Celestial Fury (part of a mod) and also 6 random guys (Shadow Druid/Fighter/Wizard Slayer/Conjurer/Beserker/something else). Also, the leader of the Cowled Wizard enforcement agency shows up when I cast stoneskin as part of contingency.
Needless to say that was a hell of a battle, I wont it though..albeit 30 minutes later.
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