I have a PR up at WPT with a bunch of tests around @font-face and shadow trees: https://github.com/web-platform-tests/wpt/pull/44993 These are based on the spec (https://drafts.csswg.org/css-scoping/#shadow-names) which WebKit gets right much more than the other engines (all but two of the tests pass) but @font-face names are meant to be tree-scoped, which WebKit does not do. So the two tests (001 and 005) that check that a @font-face rule defined in a shadow tree does not get used when referred to by the outside document fail in WebKit.
<rdar://problem/124643482>
Hi Alan, Thank you very much for the detailed bug report, we will look into it.