Returning to the OPs problem.
Assuming you are using the correct bleed nipples as there are two types of seal. One is wear the angle of the nipple is the same as the angle of the seat & the other where the nipple is pointier than the seat and relies on point contact to seal.
It's possible that somebody has drilled out a nipple in the past and damaged the seat or oval'd the hole
carandimage The place where Off-Topic is On-Topic
I used to think I was anal-retentive until I started getting involved in car forums
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