diff --git a/crates/html/src/cascade/build.rs b/crates/html/src/cascade/build.rs
index 2eccce1b5..70218d257 100644
--- a/crates/html/src/cascade/build.rs
+++ b/crates/html/src/cascade/build.rs
@@ -141,9 +141,14 @@ pub fn collect_static_css_text(
     style_texts.join("\n")
 }
 
+// A quoted url cannot span a line and an unquoted one cannot hold
+// whitespace, quotes, parens, braces, or semicolons (CSS syntax), so a
+// stray `url(` can never pair with a `)` in a later rule.
 static CSS_URL_RE: Lazy<Regex> = Lazy::new(|| {
-    Regex::new(r#"(?i)url\(\s*(?:"((?:[^"\\]|\\.)*)"|'((?:[^'\\]|\\.)*)'|([^)"']*?))\s*\)"#)
-        .expect("CSS_URL_RE")
+    Regex::new(
+        r#"(?i)url\(\s*(?:"((?:[^"\\\n\r]|\\.)*)"|'((?:[^'\\\n\r]|\\.)*)'|([^)"'(\s{};]*))\s*\)"#,
+    )
+    .expect("CSS_URL_RE")
 });
 static URL_SCHEME_RE: Lazy<Regex> =
     Lazy::new(|| Regex::new(r"^[A-Za-z][A-Za-z0-9+.-]*:").expect("URL_SCHEME_RE"));
@@ -153,8 +158,26 @@ static URL_SCHEME_RE: Lazy<Regex> =
 /// directory has its relative urls rewritten to page-relative form here.
 /// This is what lets the sampled-contrast path (#560) resolve the image the
 /// winning declaration named. Root-relative, remote, `data:`, fragment, and
-/// escaped urls are left as they are.
+/// escaped urls are left as they are, and comments are copied through
+/// untouched, so nothing inside one can reach the rules after it.
 pub fn rewrite_sheet_urls(css: &str, sheet_dir: &str, page_dir: &str) -> String {
+    let mut out = String::with_capacity(css.len());
+    let mut rest = css;
+    while let Some(start) = rest.find("/*") {
+        out.push_str(&rewrite_code_urls(&rest[..start], sheet_dir, page_dir));
+        // An unclosed comment runs to the end of the sheet, as in CSS.
+        let end = rest[start + 2..]
+            .find("*/")
+            .map(|i| start + 2 + i + 2)
+            .unwrap_or(rest.len());
+        out.push_str(&rest[start..end]);
+        rest = &rest[end..];
+    }
+    out.push_str(&rewrite_code_urls(rest, sheet_dir, page_dir));
+    out
+}
+
+fn rewrite_code_urls(css: &str, sheet_dir: &str, page_dir: &str) -> String {
     CSS_URL_RE
         .replace_all(css, |caps: &regex::Captures| {
             let whole = caps.get(0).map(|m| m.as_str()).unwrap_or("");
diff --git a/crates/html/tests/cascade_units.rs b/crates/html/tests/cascade_units.rs
index 84098b404..4afd266ed 100644
--- a/crates/html/tests/cascade_units.rs
+++ b/crates/html/tests/cascade_units.rs
@@ -360,7 +360,8 @@ fn linked_sheet_urls_are_rewritten_page_relative() {
     );
     assert!(out.contains("url(https://cdn.example.com/a.png)"), "{out}");
     assert!(out.contains("url(#clip)"), "{out}");
-    assert!(out.contains("url(\"css/a b.png\")"), "{out}");
+    // An unquoted url with a space is not a url token in CSS; it stays put.
+    assert!(out.contains("URL( a b.png )"), "{out}");
     // A sheet beside the page keeps every path where it was (the engine
     // does not even call the rewrite for that case).
     let same = rewrite_sheet_urls(css, "/site", "/site");
@@ -369,4 +370,23 @@ fn linked_sheet_urls_are_rewritten_page_relative() {
     // A sheet above the page walks back up.
     let up = rewrite_sheet_urls(".a { background: url(light.png) }", "/site", "/site/pages");
     assert_eq!(up, ".a { background: url(../light.png) }");
+    // A stray `url(` in a comment, or an unclosed quote, never swallows the
+    // rules after it: comments pass through untouched and a url form ends
+    // where CSS says it ends.
+    let hazards = concat!(
+        "/* see url( for details */ .g { color: red }\n",
+        ".h { background: url(a.png) }\n",
+        ".i { background: url(\"oops }\n",
+        ".j { background: url(b.png) }\n",
+        "/* url(unterminated.png",
+    );
+    let out = rewrite_sheet_urls(hazards, "/site/css", "/site");
+    assert!(
+        out.contains("/* see url( for details */ .g { color: red }"),
+        "{out}"
+    );
+    assert!(out.contains(".h { background: url(css/a.png) }"), "{out}");
+    assert!(out.contains(".i { background: url(\"oops }"), "{out}");
+    assert!(out.contains(".j { background: url(css/b.png) }"), "{out}");
+    assert!(out.ends_with("/* url(unterminated.png"), "{out}");
 }