PDFOutliner 4+

I needed to add a TOC to a PDF I was building, and couldn’t do it while I was generating the content, so PDFOutliner came in handy for me. I did note some quirks while adding TOC entries; the most annoying was that when entering the name of a TOC entry, all I saw was vertical bars for each character I typed, so I was typing blind. When done with entry, the name showed up normally, and re-editing worked as expected. Also, the page number would occasionally be off by one from the page I had highlighted. This was easy enough to fix, and I quickly learned to look at the page number it wanted to assign and change it while adding the TOC item.

Not as polished as I would like, but it does the job I need it to do and that was worth the price of the app.

PDFOutliner works great on El Capitan even though version 1.4 has not been updated since October 2012.

PDFOutliner creates and edits the Table of Contents for PDFs. It does one thing and does it exceedlingly well! The splash screen help file is simple, direct and easy to understand. I was able to auto generate a 3-level TOC for a nine chapter, 200 page PDF in about five minutes after first opening PDFOutliner. The two automatic TOC generators, AutoTOC and MiniTOC, create separate TOC which are easy to hand edit, tweek, or merge. The manual drag-n-drop "Push Text” and "Solo Editing” features are equally intuitive. Thus far I’ve created the TOC for a dozen or so PDFs between 200 and 500 pages each without encountering any errors or crashs.

Install the 7-day trial version from the developer’s website for a free test drive. I did and promptly bought the paid version after completing my first TOC.

I bought this just fot creating a TOC from PDFs that didn't have one. Using the auto-outline feature makes almost perfect outlines. If you choose the highest outline depth, it will pretty much do the trick. The only thing I had to change were the chapter headings. It would miss the first and second letter sometimes (i.e. 'apter' instead of 'Chapter 4'). Other than that it works good and makes the levels correctly. I bought another app named similary "PDFOutline" (do not confuse with this app "PDFOutliner". The former would crash and not make the levels correctly. It was a horrible application. This one is wayyy better. I got robbed with the other purchase.