diff --git a/packages/site-kit/src/lib/markdown/renderer.ts b/packages/site-kit/src/lib/markdown/renderer.ts
index 8eb687e31a..dcf321ea60 100644
--- a/packages/site-kit/src/lib/markdown/renderer.ts
+++ b/packages/site-kit/src/lib/markdown/renderer.ts
@@ -3,7 +3,7 @@ import { createHash } from 'node:crypto';
 import { mkdir, readFile, readdir, stat, writeFile } from 'node:fs/promises';
 import path from 'node:path';
 import ts from 'typescript';
-import { SHIKI_LANGUAGE_MAP, escape, normalizeSlugify, transform } from './utils';
+import { SHIKI_LANGUAGE_MAP, escape, normalizeSlugify, smart_quotes, transform } from './utils';
 import type { Declaration, TypeElement, Modules } from './index';
 
 type MetadataKeys = 'file' | 'link' | 'copy';
@@ -235,6 +235,7 @@ async function parse({
 
 	/** @type {string} */
 	const content = await transform(body, {
+		text: smart_quotes,
 		heading(html, level, raw) {
 			const title = html
 				.replace(/<\/?code>/g, '')
diff --git a/packages/site-kit/src/lib/markdown/utils.ts b/packages/site-kit/src/lib/markdown/utils.ts
index 750816cb81..7b19e0731c 100644
--- a/packages/site-kit/src/lib/markdown/utils.ts
+++ b/packages/site-kit/src/lib/markdown/utils.ts
@@ -78,6 +78,20 @@ export const normalizeSlugify = (str: string) => {
 	return slugify(removeHTMLEntities(removeMarkdown(str))).replace(/(<([^>]+)>)/gi, '');
 };
 
+export function smart_quotes(str: string) {
+	// replace dumb quotes with smart quotes. This isn't a perfect algorithm — it
+	// wouldn't correctly handle `That '70s show` or `My country 'tis of thee`
+	// but a) it's very unlikely they'll occur in our docs, and
+	// b) they can be dealt with manually
+	return str.replace(/(.|^)(&#39;|&quot;)(.|$)/g, (m, before, quote, after) => {
+		const left = !before.trim();
+		const double = quote === '&quot;';
+		const entity = `&${left ? 'l' : 'r'}${double ? 'd' : 's'}quo;`;
+
+		return (before ?? '') + entity + (after ?? '');
+	});
+}
+
 const default_renderer: Partial<Renderer> = {
 	code(code, infostring, escaped) {
 		const lang = infostring?.match(/\S*/)?.[0];
diff --git a/packages/site-kit/src/lib/server/content/index.ts b/packages/site-kit/src/lib/server/content/index.ts
index 2b31976cb9..49392ec36d 100644
--- a/packages/site-kit/src/lib/server/content/index.ts
+++ b/packages/site-kit/src/lib/server/content/index.ts
@@ -1,4 +1,4 @@
-import { extract_frontmatter, slugify } from '../../markdown/utils';
+import { extract_frontmatter, slugify, smart_quotes } from '../../markdown/utils';
 import type { Document } from '../../types';
 
 export async function create_index(
@@ -24,6 +24,9 @@ export async function create_index(
 			throw new Error(`Missing title in ${slug} frontmatter`);
 		}
 
+		metadata.title = smart_quotes(metadata.title);
+		if (metadata.description) metadata.description = smart_quotes(metadata.description);
+
 		const sections = Array.from(body.matchAll(/^##\s+(.*)$/gm)).map((match) => {
 			const title = match[1].replace(/`/g, '').replace(/&lt;/g, '<').replace(/&gt;/g, '>');
 			const slug = slugify(title);