diff --git a/crates/pdf/src/lib.rs b/crates/pdf/src/lib.rs
index 97eb641b..43da6abb 100644
--- a/crates/pdf/src/lib.rs
+++ b/crates/pdf/src/lib.rs
@@ -300,8 +300,7 @@ impl Exporter<'_> {
             }
             let Some(font) = self.font(&run.face) else { continue };
             let n = run.glyphs.len();
-            let char_starts: Vec<usize> = text.char_indices().map(|(b, _)| b).chain(std::iter::once(text.len())).collect();
-            let one_to_one = char_starts.len() - 1 == n;
+            let ranges = glyph_text_ranges(&text, run.chars, &run.cells, n);
             let (x0, y0) = (run.glyphs[0].1, run.glyphs[0].2);
             let kg: Vec<KrillaGlyph> = run
                 .glyphs
@@ -309,13 +308,7 @@ impl Exporter<'_> {
                 .enumerate()
                 .map(|(gi, g)| {
                     let next = run.glyphs.get(gi + 1).map_or(g.1 + run.face.advance(g.0) * run.size / run.face.upem.max(1.0), |nx| nx.1);
-                    let range = if one_to_one {
-                        char_starts[gi]..char_starts[gi + 1]
-                    } else if gi == 0 {
-                        0..text.len()
-                    } else {
-                        text.len()..text.len()
-                    };
+                    let range = ranges[gi].clone();
                     KrillaGlyph::new(GlyphId::new(g.0), ((next - g.1) / run.size) as f32, 0.0, ((g.2 - y0) / run.size) as f32, 0.0, range, None)
                 })
                 .collect();
@@ -423,6 +416,20 @@ impl Exporter<'_> {
     }
 }
 
+/// Byte range in `text` (the run's characters `chars`) of each of `n` glyphs, for the ToUnicode map.
+/// `cells` holds each glyph's shaping-cluster head (paragraph character index); a cluster runs to the
+/// next head in the run, so a ligature maps to all its characters and every glyph of a cluster shares
+/// its range (krilla then writes the text once).
+fn glyph_text_ranges(text: &str, chars: (usize, usize), cells: &[(usize, char)], n: usize) -> Vec<std::ops::Range<usize>> {
+    let starts: Vec<usize> = text.char_indices().map(|(b, _)| b).collect();
+    let byte = |ci: usize| ci.checked_sub(chars.0).and_then(|i| starts.get(i).copied()).unwrap_or(text.len());
+    let mut heads: Vec<usize> = cells.iter().map(|c| c.0).collect();
+    heads.sort_unstable();
+    heads.dedup();
+    let end = |ci: usize| heads.get(heads.partition_point(|&h| h <= ci)).copied().unwrap_or(chars.1);
+    (0..n).map(|gi| cells.get(gi).map_or(text.len()..text.len(), |&(ci, _)| byte(ci)..byte(end(ci)))).collect()
+}
+
 fn to_path(bp: &kurbo::BezPath) -> Option<krilla::geom::Path> {
     use kurbo::PathEl;
     let mut pb = krilla::geom::PathBuilder::new();
diff --git a/crates/pdf/src/tests.rs b/crates/pdf/src/tests.rs
index 305f1457..ffc18b40 100644
--- a/crates/pdf/src/tests.rs
+++ b/crates/pdf/src/tests.rs
@@ -66,3 +66,13 @@ fn handout_boxes_fit_the_paper() {
         }
     }
 }
+
+#[test]
+fn glyph_ranges_follow_shaping_clusters() {
+    // "fl" ligature: its glyph maps to both characters, the rest stay one to one (#164).
+    assert_eq!(glyph_text_ranges("flash", (0, 5), &[(0, 'f'), (2, 'a'), (3, 's'), (4, 'h')], 4), vec![0..2, 2..3, 3..4, 4..5]);
+    // Two glyphs in one cluster (base and mark) share its range.
+    assert_eq!(glyph_text_ranges("ab", (0, 2), &[(0, 'a'), (0, 'a'), (1, 'b')], 3), vec![0..1, 0..1, 1..2]);
+    // A run starting mid-paragraph, multi-byte characters in visual (right-to-left) order.
+    assert_eq!(glyph_text_ranges("αβγ", (3, 6), &[(5, 'γ'), (4, 'β'), (3, 'α')], 3), vec![4..6, 2..4, 0..2]);
+}