I noticed several typefaces recently failed to appear on my website, including two I often use; namely, Iowan Old Style and Seravek.

My normal method for checking whether a font is installed is to open Pages and see if it’s in the font list. Lo and behold, Iowan Old Style and Seravek weren’t there.
I’ve no idea how Apple negotiates typeface licenses – I’d assume they’d run in perpetuity, because you might come to depend on certain fonts. It’s not something you think about.
Take choosing fonts for websites. One performance strategy is to use native instead of webfonts as this saves your visitors from downloading dozens or even hundreds of kbs of font files. You can be creative with native fonts – take this old style serif stack suggested by Modern Font Stacks:
font-family: 'Iowan Old Style', 'Palatino Linotype', 'URW Palladio L', P052, serif;
Which on my laptop doesn’t look like an old style serif because Iowan Old Style is no more (it’s showing STIX Two Text, my default Firefox serif):

Even if we’re not using native fonts creatively, imagine the problems across the web if this became an unpredictable line of code:
font-family: georgia, serif;
Why did my fonts disappear?
I initially assumed Apple had simply stopped including the fonts in MacOS. Brutal, but at least I’d have an explanation. It turns out not to be quite as simple – a quick search revealed disappearing fonts is a known issue. Simone responded to my post about the problem, saying that he could see both fonts in Safari – as can I.
I decided to check my system fonts folder to see if Iowan Old Style is in fact there, and it is – in the Supplemental subfolder.

So why does Iowan Old Style appear in some MacOS apps, but not others? What I did note was the file extension – .ttc – rather than the more familiar .ttf. True Type Collection files bundle several fonts (different weights, italics etc.) into one typeface file, like a sort of .zip. While some .ttc files appear in many MacOS apps (Hoefler Text, for example), others don’t. All .ttf files work as expected.
So the problem seems to be down to the way some .ttc packages are created and/or how some MacOS apps use them. Regardless, as Apple distributes the files and they don’t appear to work in some Apple apps for many users, it’s for Apple to fix.