Why does disabling Pretty URLs not disable Pretty URLs?

Hi, @miles. This topic is a duplicate of this topic you created recently:

Please do not create duplicate topics as this makes the support forum less useful to others, it creates unnecessary work for our support team, and it just slows down our responses.

About the upper bounds for redirect counts, there is nothing documented officially. I would recommend, for performance reasons, to limit the number of redirect per site to 2000 or fewer.