I worked on a bot that parses NDAs using (among other things) flags, regexes and ML to tell you if you could sign it. In the end from all the files that had to

I worked on a bot that parses NDAs using (among other things) flags, regexes and ML to tell you if you could sign it. In the end from all the files that had to be parsed (doc, docx, txt, rtf and pdf) PDF was the most troublesome. When parsing a PDF nothing was 100% certain. In the end it was one of the most interesting projects I worked on in my (short) career but sometimes it sucked.