pillagers and captains illagers do not re-generate after initials die on pillager outpost
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It works at night only. 1.11.4 has changed caption spawn to by a chance every between few packs. It makes sense for us to fight until we get the caption. 2-5 packs between so far in my test. This might not be permanent mechanic i believe they are still working on it.
Edit: Disregard my comment above, pillagers would respawn in the dark any time of day.

I have found a pillager outpost in my world, and there's too few pillagers, only 4. So, I tried to change game difficulty to peaceful, and again to hard to see if can spawn more pillagers. But I can't see any pillager spawning. So, I've tried to take a look in criative mode, and figure it out pillagers in Outpost are only spawning at night. And for me, this is really strange!Β Other thing that I noticed is not even a creeper is spawning when is during day, I don't know why, but I think that is a too low spawn rate during the day
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they did in 1.11.3 but it wasnt a 100% affair. i had to reload the chunk several times to force a single respawn. currently, its the only way i can generate a natural bad omen effect as i cant find any patrols... off the cuff, i would rate outpost respawns at something like 5%.