Another update - I added my plumbers tape and I flipped the internal O ring. It got shredded a little because I pushed too hard with my drill and I kind of have a tiny lip on the inside of the kettle.
This time I tightened it less aggressively, just hand tightened with one turn with a wrench. I will test it for leaks this weekend.
FOR THE LIFE OF ME, I was unable to get the dip tube to push through the 2 O rings in the bulk head. I even tried wetting it and using keg lube. Idk wtf is wrong.
I was able to easily get the inner attachment that is meant for a mash tun inside though. And I think I'll just resolve to tipping the kettle for the last bit of wort, because it was way too much effort trying to push that thing in (prob tried for like 30 minutes).