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"I had two playthroughs. In the first one, I only made agreements with the rulers. I wanted to check whether it was necessary to complete the game.
In the second, I also only made the agreements with the rulers to see if it was due to the game. Again, about 100.
After that I only made the agreements with the rogue guild etc. and kept a tally. After 50 agreements I had the achievement.
As soon as you can build the appropriate buildings you can destroy the armies from Glouchester again and again. They appear every 4-5 rounds after you destroy them. You have to destroy them to be able to complete further agreements.
Hope that helps one to reproduce it."
The other agreements of the rulers do not seem to count.
Conqueror works, you just have to win 10 battles while holding every victory locations.
https://forum.paradoxplaza.com/forum/threads/achievement-guide.630649/