can't over-write existing file
Mac OS 10.14 - Illustrator 24.0.2
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Anonymous
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Nils Wasser commented
Had the same issue.
I tried to override a PDF and Illustrator saves it (save dialogue), but the file remains the old one.
(Finder shows no difference to "Created" / "Edited" date).I had to delete the PDF file to save the new one with the same name.