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You don't have to compile the same file a magic number of times. You either click the button in your GUI or you use latexmk or texify.

The error messages suck though, that's true.

Does GUI LaTeX tools run the compilation several times in the background? Because last time I checked, you absolutely had to run it several times, if you wanted to have all your references correct.

EDIT: nevermind, I didn't know Latexmk is a thing and is popular.

Lyx for one does run latex/bibtex as many times as required.

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