Instead of the setting “Until end of paragraph”, use: “until right-indent tab”.
LiveTOC is going to search from the first word until whatever you tell it. If you tell it “end of paragraph” it will search for a chapter title that includes a right-indent tab and the page number, so obviously it will never find it, because that doesn’t exist in the book.
(When there is a soft break in the TOC, it stops searching there, and so finds the paragraph.)
It’s not usually necessary to run LiveTOC twice on the same TOC entry (since the page numbers automatically update). But if you do, make sure to change the existing cross-referenced page number back to 000, so that LiveTOC will know where to add the new page number.