Links in PDF containing # not working in Safari

Had a chance to try your PDF directly out of Acrobat DC Pro. All worked in Safari, with the minor exception the last two both said the connection wasn't private, so I didn't follow those through. But the first two had no problem at all.

However, if I open the same PDF in Preview and then try the links, the first two only partially load in Safari with this error as part of the page rendering:

So I'd have to say Preview is doing something wrong when passing the link to Safari. Which isn't exactly surprising since Preview is always behind the current PDF standards.

What ever placed the reference link in your PDF document was enforcing RFC3986 and converting the reserved (#) character to the replacement string %23. See Percent_Encoding. Any internal change of the destination page could also adversely affect the URL anchor reference from working at all.

I just exported a Pages document to PDF (without) the percent encoding, and here is what I see inside the PDF:

No conversion to %23. This link works correctly from Preview, or when the PDF is opened directly in Safari — the browser is not performing any percent encoding on the link, and it is opened to its anchor (#) location on the target site.

When I deliberately change the Page's URL to one with a %23 encoding for the '#' character, and export to PDF, that PDF has the following string in it:

The URL is changed from what was entered in Page's Link Editor to the normal URL with identical results to the previous.

I clicked on your link containing the # just now in Safari and it worked as expected.

You may have an extension installed that is causing the problem. Open Safari's preferences, then click on the Extensions tab. Temporarily disable any there. Try your link again.