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Everything you wrote sounds about right, so it may be that he just needed to get one extra line of dialogue out in his prison cell.
I've heard going down to the Profaned Capital before doing Anor Londo can mess up certain questlines.
I have no need for it, personally.
Same thing happened to me. I was sure to exhaust all the dialogues with him, went into the boss fight, and siegward never appeared. Because cutscene wasnt coming out, i even used homeward bone to make sure i get him.
He still didnt come. I think there is some problem with him rn.