diff --git a/src/servers/api/dev-proxy/html-rewrite.test.ts b/src/servers/api/dev-proxy/html-rewrite.test.ts
index 40865792..f5293c78 100644
--- a/src/servers/api/dev-proxy/html-rewrite.test.ts
+++ b/src/servers/api/dev-proxy/html-rewrite.test.ts
@@ -1,5 +1,5 @@
 import { describe, expect, test } from 'bun:test';
-import { proxyOverrideScript, rewriteAssetPaths, rewriteHtml } from './html-rewrite';
+import { proxyOverrideScript, rewriteAssetPaths, rewriteCss, rewriteHtml } from './html-rewrite';
 
 const BASE = '/api/dev-proxy/3001';
 const attrs = (html: string) => [...html.matchAll(/(?:src|href)="([^"]+)"/g)].map((m) => m[1]!);
@@ -212,3 +212,42 @@ describe('the injected location reporter', () => {
     expect(r.posted).toHaveLength(2);
   });
 });
+
+describe('stylesheets', () => {
+  test('a quoted url is prefixed — the form every generator emits', () => {
+    expect(rewriteCss('@font-face{src:url("/fonts/Averta.woff2") format("woff2")}', BASE)).toContain(
+      `url("${BASE}/fonts/Averta.woff2")`,
+    );
+  });
+
+  test('single quotes and bare urls too', () => {
+    expect(rewriteCss("a{background:url('/bg.png')}", BASE)).toContain(`url('${BASE}/bg.png')`);
+    expect(rewriteCss('a{background:url(/bg.png)}', BASE)).toContain(`url(${BASE}/bg.png)`);
+  });
+
+  test('the quote style is preserved, not normalised', () => {
+    expect(rewriteCss('a{background:url("/bg.png")}', BASE)).not.toContain("url('");
+  });
+
+  test('a url that is already absolute is left alone', () => {
+    const external = 'a{background:url("https://cdn.example.com/bg.png")}';
+    expect(rewriteCss(external, BASE)).toBe(external);
+    const protocolRelative = 'a{background:url("//cdn.example.com/bg.png")}';
+    expect(rewriteCss(protocolRelative, BASE)).toBe(protocolRelative);
+  });
+
+  test('a relative url is left alone — it already resolves against the stylesheet', () => {
+    const relative = 'a{background:url("./bg.png")}';
+    expect(rewriteCss(relative, BASE)).toBe(relative);
+  });
+
+  test('a stylesheet still gets the /_bun/ rule', () => {
+    expect(rewriteCss('@import "/_bun/x.css";', BASE)).toContain(`${BASE}/_bun/x.css`);
+  });
+
+  test('inline CSS in HTML gets the same treatment, quotes included', () => {
+    expect(rewriteHtml('<div style=\'background:url("/a.png")\'></div>', BASE)).toContain(
+      `url("${BASE}/a.png")`,
+    );
+  });
+});
diff --git a/src/servers/api/dev-proxy/html-rewrite.ts b/src/servers/api/dev-proxy/html-rewrite.ts
index 0510c338..4341ea64 100644
--- a/src/servers/api/dev-proxy/html-rewrite.ts
+++ b/src/servers/api/dev-proxy/html-rewrite.ts
@@ -139,12 +139,41 @@ export const rewriteHtml = (html: string, base: string) =>
       /(imagesrcset|srcset)=("|')([^"']*)\2/gi,
       (_match, attr: string, quote: string, list: string) => `${attr}=${quote}${prefixSrcset(base, list)}${quote}`,
     )
-    .replace(/url\((\/(?!\/)[^)"']*)\)/g, (_match, path: string) => `url(${prefix(base, path)})`);
+    .replace(CSS_URL, cssUrlPrefixer(base));
 
-// JS/CSS: only `/_bun/` paths.
+/*
+  `url(/…)` — a font, a background image, an `@import`. CSS allows the target bare, single-quoted or
+  double-quoted, and all three mean the same thing, so all three have to match. The quote used is
+  captured and put back rather than normalised: rewriting is not the place to have an opinion about
+  someone else's stylesheet.
+
+  This rule missed every QUOTED url until 2026-08-31, which is a bad way to fail. `url(/x.png)` was
+  rewritten and `url("/x.png")` was not, so whether a stylesheet worked through the proxy came down to
+  the formatting preference of whatever generated it.
+*/
+const CSS_URL = /url\(\s*(["']?)(\/(?!\/)[^)"']*)\1\s*\)/g;
+
+const cssUrlPrefixer =
+  (base: string) =>
+  (_match: string, quote: string, path: string): string =>
+    `url(${quote}${prefix(base, path)}${quote})`;
+
+// JS: only `/_bun/` paths.
 //
 // Deliberately narrow. A blanket rewrite of every absolute path inside JavaScript hits strings that are
 // not URLs — a regex in the source, a route table, anything containing a slash — and corrupts the file it
 // is trying to fix. Bun's dev server emits its chunk imports under `/_bun/`, which is specific enough to
 // match safely. A Vite app instead wants `base` set in its own config; nothing here can guess that.
 export const rewriteAssetPaths = (text: string, base: string) => text.replace(/\/_bun\//g, `${base}/_bun/`);
+
+/*
+  A STYLESHEET gets more than that, because a stylesheet's absolute paths are unambiguous: `url(/…)` is
+  a URL and nothing else, so the argument for being narrow in JavaScript does not apply here.
+
+  This was the whole of it for a long time, and the symptom was specific: a site's own `@font-face` rules
+  kept pointing at `/fonts/…`, which inside the frame is the PLATFORM's root, so every face 404'd and the
+  preview quietly rendered in a system fallback. Nothing looked broken — it just looked like a different
+  site than the one being previewed, which is the one thing a preview must never do.
+*/
+export const rewriteCss = (text: string, base: string) =>
+  rewriteAssetPaths(text, base).replace(CSS_URL, cssUrlPrefixer(base));
diff --git a/src/servers/api/dev-proxy/router.ts b/src/servers/api/dev-proxy/router.ts
index 683fec32..c27f5d57 100644
--- a/src/servers/api/dev-proxy/router.ts
+++ b/src/servers/api/dev-proxy/router.ts
@@ -1,7 +1,7 @@
 import { createRouter } from '../../create-router';
 import { resolveAuthToken } from '../../auth-token';
 import { isSuperAdmin } from '../../super-admin';
-import { rewriteAssetPaths, rewriteHtml } from './html-rewrite';
+import { rewriteAssetPaths, rewriteCss, rewriteHtml } from './html-rewrite';
 
 /**
  * See a dev server running on THIS machine's loopback, from a browser that is somewhere else.
@@ -145,7 +145,8 @@ devProxyRouter.all('/:port/*', async (ctx) => {
 
   const type = res.headers.get('content-type') ?? '';
   const isHtml = type.includes('text/html');
-  const rewritable = isHtml || type.includes('javascript') || type.includes('text/css');
+  const isCss = type.includes('text/css');
+  const rewritable = isHtml || isCss || type.includes('javascript');
 
   const headers = new Headers(res.headers);
   // Anything framed here is the owner's own dev server; the platform frames it deliberately.
@@ -169,7 +170,11 @@ devProxyRouter.all('/:port/*', async (ctx) => {
   }
 
   const text = await res.text();
-  const body = isHtml ? rewriteHtml(text, prefix) : rewriteAssetPaths(text, prefix);
+  const body = isHtml
+    ? rewriteHtml(text, prefix)
+    : isCss
+      ? rewriteCss(text, prefix)
+      : rewriteAssetPaths(text, prefix);
   // Both are wrong after a rewrite: the length changed, and the body was decoded on the way through.
   headers.delete('content-length');
   headers.delete('content-encoding');