1. please define "Mac .pdf file". Which software did you use to create the document?
2. what are the steps you followed to extract the information needed ("hash") from the .pdf document?
3. How did you try "all the Adobe PDF hash types"? If you've followed the steps, you should have extracted the "hash" and therefore you should know which hash type it is (also by looking at the example hash page: https://hashcat.net/wiki/doku.php?id=example_hashes ). So trying "all the Adobe PDF hash types" doesn't really make sense and maybe means that you either did not have extracted the "hash" at all and/or you do not know how to match that output to the correct hash type (there are actually 2 things that should make the hash type clear: 1. by identifying the software (version) the pdf was generated, 2. the extracted "hash" information itself).
Also see: https://hashcat.net/wiki/frequently_aske..._documents and the dozens of forum posts that explain it (also use the forum search function).
2. what are the steps you followed to extract the information needed ("hash") from the .pdf document?
3. How did you try "all the Adobe PDF hash types"? If you've followed the steps, you should have extracted the "hash" and therefore you should know which hash type it is (also by looking at the example hash page: https://hashcat.net/wiki/doku.php?id=example_hashes ). So trying "all the Adobe PDF hash types" doesn't really make sense and maybe means that you either did not have extracted the "hash" at all and/or you do not know how to match that output to the correct hash type (there are actually 2 things that should make the hash type clear: 1. by identifying the software (version) the pdf was generated, 2. the extracted "hash" information itself).
Also see: https://hashcat.net/wiki/frequently_aske..._documents and the dozens of forum posts that explain it (also use the forum search function).