diff --git a/crates/optimize/src/images.rs b/crates/optimize/src/images.rs
index 57e583a078..33e60256e0 100644
--- a/crates/optimize/src/images.rs
+++ b/crates/optimize/src/images.rs
@@ -604,6 +604,59 @@ fn mono(doc: &Document, s: &Stream, compression: MonoCompression) -> Option<Stre
     (crate::stored_len(&new)? < crate::stored_len(s)?).then_some(new)
 }
 
+/// An eight-bit grey image whose every sample is 0 or 255, stored at one bit per pixel and then as
+/// `compression` asks (see [`mono`]), if that is smaller as stored. Lossless: a decode array maps
+/// 0 and 255 at eight bits as it maps 0 and 1 at one bit, so it stays. Left alone: indexed images
+/// (their samples are palette indices), a colour-key `/Mask` (its ranges are in eight-bit values),
+/// and everything when `compression` is Retain.
+fn bilevel_grey(doc: &Document, s: &Stream, compression: MonoCompression) -> Option<Stream> {
+    if compression == MonoCompression::Retain {
+        return None;
+    }
+    let d = &s.dict;
+    let indexed = |cs: &Object| match &*doc.resolve(cs) {
+        Object::Array(a) => matches!(a.first().and_then(Object::as_name), Some(b"Indexed" | b"I")),
+        _ => false,
+    };
+    let colour_key = d.get(b"Mask").is_some_and(|m| doc.resolve(m).as_array().is_some());
+    if d.int(b"BitsPerComponent") != Some(8)
+        || matches!(d.get(b"ImageMask"), Some(Object::Bool(true)))
+        || colour_key
+        || !d.get(b"ColorSpace").is_some_and(|cs| one_component(doc, cs) && !indexed(cs))
+    {
+        return None;
+    }
+    // Through u32 first, as everywhere here, so the product can't overflow.
+    let (w, h) = (u32::try_from(d.int(b"Width")?).ok()?, u32::try_from(d.int(b"Height")?).ok()?);
+    if w == 0 || h == 0 || u64::from(w) * u64::from(h) > MAX_PIXELS {
+        return None;
+    }
+    let (w, h) = (usize::try_from(w).ok()?, usize::try_from(h).ok()?);
+    let samples = s.decoded().ok()?;
+    let samples = samples.get(..w.checked_mul(h)?)?;
+    let stride = w.div_ceil(8);
+    let mut packed = vec![0u8; stride.checked_mul(h)?];
+    for (i, v) in samples.iter().enumerate() {
+        match v {
+            0 => {}
+            255 => {
+                if let Some(b) = packed.get_mut((i / w) * stride + (i % w) / 8) {
+                    *b |= 0x80 >> (i % w % 8);
+                }
+            }
+            _ => return None,
+        }
+    }
+    let mut one_bit = d.clone();
+    for k in [&b"Filter"[..], b"DecodeParms", b"Length", b"DL"] {
+        one_bit.remove(k);
+    }
+    one_bit.set(b"BitsPerComponent".to_vec(), Object::Int(1));
+    let one_bit = Stream::flate(one_bit, &packed);
+    let best = mono(doc, &one_bit, compression).unwrap_or(one_bit);
+    (crate::stored_len(&best)? < crate::stored_len(s)?).then_some(best)
+}
+
 pub(crate) fn run(
     doc: &mut Document,
     pages: &[ObjRef],
@@ -630,7 +683,7 @@ pub(crate) fn run(
         let obj = doc.get(r);
         let Object::Stream(s) = &*obj else { continue };
         report.images += 1;
-        if let Some(new) = mono(doc, s, settings.mono) {
+        if let Some(new) = mono(doc, s, settings.mono).or_else(|| bilevel_grey(doc, s, settings.mono)) {
             report.image_bytes_before += s.raw.len();
             report.image_bytes_after += new.raw.len();
             report.images_recompressed += 1;
diff --git a/crates/optimize/tests/optimize.rs b/crates/optimize/tests/optimize.rs
index 3fce1dadba..8993c598f8 100644
--- a/crates/optimize/tests/optimize.rs
+++ b/crates/optimize/tests/optimize.rs
@@ -588,6 +588,76 @@ fn images_whose_data_decodes_far_past_their_samples_are_left_alone() {
     assert!(stream(&doc, eight_bit).dict.int(b"Width").is_some_and(|nw| nw < i64::from(w)), "8-bit hex text in lines: resampled");
 }
 
+/// Eight-bit samples (0 or 255) from rows of one-bit ones.
+fn eight_bit(bits: &[u8], w: u32, h: u32) -> Vec<u8> {
+    let stride = (w as usize).div_ceil(8);
+    (0..h as usize).flat_map(|y| (0..w as usize).map(move |x| if bits[y * stride + x / 8] & (0x80 >> (x % 8)) != 0 { 255 } else { 0 })).collect()
+}
+
+/// Eight-bit grey images of only black and white (as some scanners and converters write scans)
+/// become one-bit Group 4, losslessly: the page looks the same, an inverting decode array
+/// included. Not touched by this: a grey image with any other shade, an indexed image (its samples
+/// are palette indices), one masked by colour key, and everything with `mono: Retain`.
+#[test]
+fn eight_bit_black_and_white_images_become_one_bit() {
+    let mut doc = Document::new_empty();
+    let (w, h) = (1200, 480);
+    let grey = eight_bit(&bilevel(w, h, false), w, h);
+    let image = |doc: &mut Document, data: &[u8], entries: &[(&str, Object)]| {
+        let mut d = Dict::new();
+        d.set(b"Type".to_vec(), Object::name("XObject"));
+        d.set(b"Subtype".to_vec(), Object::name("Image"));
+        d.set(b"Width".to_vec(), Object::Int(w as i64));
+        d.set(b"Height".to_vec(), Object::Int(h as i64));
+        d.set(b"BitsPerComponent".to_vec(), Object::Int(8));
+        for (k, v) in entries {
+            d.set(k.as_bytes().to_vec(), v.clone());
+        }
+        doc.add(Object::Stream(Stream::flate(d, data)))
+    };
+    let gray_cs = ("ColorSpace", Object::name("DeviceGray"));
+    let plain = image(&mut doc, &grey, std::slice::from_ref(&gray_cs));
+    let decode = Object::Array(vec![1.into(), 0.into()]);
+    let inverted = image(&mut doc, &grey, &[gray_cs.clone(), ("Decode", decode.clone())]);
+    let mut shaded = grey.clone();
+    shaded[1000] = 128;
+    let shade = image(&mut doc, &shaded, std::slice::from_ref(&gray_cs));
+    let palette = Object::Array(vec![
+        Object::name("Indexed"),
+        Object::name("DeviceGray"),
+        255.into(),
+        Object::String(pdfcraft_cos::PdfString::literal((0..=255u8).rev().collect::<Vec<_>>())),
+    ]);
+    let indexed = image(&mut doc, &grey, &[("ColorSpace", palette)]);
+    let keyed = image(&mut doc, &grey, &[gray_cs, ("Mask", Object::Array(vec![0.into(), 0.into()]))]);
+    page(
+        &mut doc,
+        &[("A", plain), ("B", inverted), ("C", shade), ("D", indexed), ("E", keyed)],
+        "q 300 0 0 120 20 660 cm /A Do Q q 300 0 0 120 320 660 cm /B Do Q q 300 0 0 120 20 520 cm /C Do Q \
+         q 300 0 0 120 320 520 cm /D Do Q q 300 0 0 120 20 380 cm /E Do Q",
+    );
+    let before = render(&doc);
+    let raw = |doc: &Document, r: ObjRef| stream(doc, r).raw;
+    // Grey settings that leave grey images alone, so only this conversion acts.
+    let keep = ImageSettings { downsample: false, target_ppi: 150.0, above_ppi: 225.0, compression: Compression::Retain };
+    let settings = Settings { gray: keep, ..Settings::default() };
+
+    let mut kept = doc.clone();
+    let r = optimize(&mut kept, &Settings { mono: MonoCompression::Retain, ..settings.clone() }).unwrap();
+    assert_eq!(r.images_recompressed, 0, "Retain keeps every image as it is");
+
+    let untouched = [shade, indexed, keyed].map(|r| raw(&doc, r));
+    let r = optimize(&mut doc, &settings).unwrap();
+    assert_eq!(r.images_recompressed, 2);
+    for i in [plain, inverted] {
+        let s = stream(&doc, i);
+        assert_eq!((s.dict.int(b"BitsPerComponent"), s.dict.name(b"Filter")), (Some(1), Some(&b"CCITTFaxDecode"[..])));
+    }
+    assert_eq!(stream(&doc, inverted).dict.get(b"Decode"), Some(&decode), "the decode array stays");
+    assert_eq!([shade, indexed, keyed].map(|r| raw(&doc, r)), untouched);
+    assert!(render(&doc) == before, "the page looks the same");
+}
+
 #[test]
 fn settings_choose_what_happens() {
     let mut doc = Document::new_empty();