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Is there any way I can force Preview to always show the table of contents when opening a PDF? Most of the PDFs I use have a ToC, so this would save me the extra step from having to enable the ToC after opening the PDF.

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This is currently not possible to be set as default in Preview. The closest you can get to this is Preferences → Opening for the first time: Always show sidebar. However, the sidebar that opens is the default thumbnail view, not the TOC.

You can provide feedback to Apple regarding this at the following page:

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