I am getting the following error now when I compile with TeXShop.

"This is pdfTeX, Version 3.14159265-2.6-1.40.16 (TeX Live 2015) (preloaded format=pdflatex)
 restricted \write18 enabled.
entering extended mode
(./Oct11.tex/Library/TeX/texbin/pdflatex: getcwd: Operation not permitted"

Any ideas how to fix it? It was working fine before updating to Catalina.

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    This has nothing to do with TeXShop. Your version of MacTeX is positively ancient (TL 2015). Please do yourself a favour and update to the latest version of MacTeX, which should work fine with Catalina. – Alan Munn Oct 9 '19 at 15:55
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    Possible solution without upgrading (which you should do of course): modify the privileges of pdflatex as in osxdaily.com/2018/10/09/…. – Marijn Oct 9 '19 at 15:59
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    @Mico I think you mean TL 2015? But TL 2015 contained 64bit binaries anyway. – Alan Munn Oct 9 '19 at 16:21
  • Thank you for your comments. I figured out that when I updated to Catalina, the new OS restricted the permissions of TeXShop since it's a downloaded software. I adjusted the permissions in the OS and it resolved the problem. – Seneca Oct 13 '19 at 20:52

It is probably a matter of application file system permission for TexShop in Catalina. : Open General Settings -> Security & Privacy -> Privacy, select Full Disk Access in the left pane, then click + and add TexShop. I had the same with Emacs and Auctex and solved it with information provided here :

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