Kramdown seems to do a good job of converting straight ' apostrophes to curly ones ’ (same goes with double quotes etc) - however it doesn’t seem to happen in titles.
Is this is technical limitation with kramdown? Do I just need to actually type out the curly quote in Front Matter?
This is a limitation of most themes. The layouts in most themes just include a site or page’s title without markdown-to-html conversion, so the title is rendered as-is from the YAML config/front-matter.
As per Jekyll’s documentation: https://jekyllrb.com/docs/liquid/filters/
Smartify
Convert “quotes” into “smart quotes.” {{ page.title | smartify }}