I see this all the time when asking Claude or ChapGPT to produce a single-page two-column PDF summarizing the conclusions of our chat. Literally 99% of the time I get a multi-page unpredictably-formatted mess, even after gently asking over and over for specific fixes to the formatting mistake/s.
And as you say, they cheerfully assert that they've done the job, for real this time, every time.
Ask for the asciidoc and asciidoctor command to make a PDF instead. Chat bots aren’t designed to make PDFs. They are just trying to use tools in the background, probably starting with markdown.
And as you say, they cheerfully assert that they've done the job, for real this time, every time.