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when would i need to come back?
I came back after I cleared Blighttown.
to get a rusty ring
For round 2 on your mom
Oh shoot, I accidentally dislike this comment instead of hitting reply

Anyways there is a doll and a ring in there that are unobtainable unless you come back for a second round

The doll gives you access to this games painted world and the 4ing allows you to run no4mally in water and the sort
Also another demon boss is available yo fight and he drops a titanite slab
What is that item on the destroyed staircase leading from the undead knight?
I believe its the rusted iron ring. The one that lets you roll/walk through deeper water with no problem.