diff --git a/tests/test_font_masking.py b/tests/test_font_masking.py
new file mode 100644
index 0000000..80e0b48
--- /dev/null
+++ b/tests/test_font_masking.py
@@ -0,0 +1,155 @@
+"""Test that detect_font_masked correctly identifies fonts even with redaction boxes."""
+import numpy as np
+from PIL import Image, ImageDraw, ImageFont
+
+from unredact.pipeline.font_detect import (
+    _find_font_path,
+    detect_font_masked,
+)
+from unredact.pipeline.ocr import OcrChar, OcrLine
+
+
+def _render_page_with_redaction(
+    font_name: str,
+    font_size: int,
+    text: str,
+    redaction_frac: tuple[float, float] = (0.4, 0.7),
+) -> tuple[OcrLine, Image.Image, list[tuple[int, int, int, int]]]:
+    """Render text onto a page image with a black redaction box.
+
+    Returns (OcrLine, page_image, redaction_boxes) where redaction_boxes
+    are (rx, ry, rw, rh) in page-relative coordinates.
+
+    The OcrLine bounding box is set to tightly wrap the rendered text
+    (mimicking what OCR would produce), so detect_font_masked can create
+    a scoring_line with x=0, y=0 that aligns correctly.
+    """
+    font_path = _find_font_path(font_name)
+    assert font_path is not None, f"Font {font_name} not found on system"
+    font = ImageFont.truetype(str(font_path), font_size)
+
+    # Measure the text
+    bbox = font.getbbox(text)
+    text_w = bbox[2] - bbox[0]
+    text_h = bbox[3] - bbox[1]
+
+    # Place the line at an offset on a larger "page" image.
+    # The line bounding box starts exactly where the text ink begins,
+    # matching what OCR would detect.
+    page_margin_x = 50
+    page_margin_y = 80
+
+    # Text is rendered at (render_x, render_y) such that ink starts at
+    # (line_x, line_y) in page coordinates.
+    line_x = page_margin_x
+    line_y = page_margin_y
+    render_x = line_x - bbox[0]
+    render_y = line_y - bbox[1]
+    line_w = text_w
+    line_h = text_h
+
+    page_w = line_x + line_w + 50
+    page_h = line_y + line_h + 100
+
+    # Render the text onto the page
+    page_img = Image.new("L", (page_w, page_h), 255)
+    draw = ImageDraw.Draw(page_img)
+    draw.text((render_x, render_y), text, font=font, fill=0)
+
+    # Build an OcrLine with approximate character positions (page-relative)
+    words = text.split()
+    chars: list[OcrChar] = []
+    cursor_x = line_x
+    for wi, word in enumerate(words):
+        word_bbox = font.getbbox(word)
+        word_w = word_bbox[2] - word_bbox[0]
+        char_w = word_w / len(word)
+        for ci, ch in enumerate(word):
+            chars.append(OcrChar(
+                text=ch,
+                x=int(cursor_x + ci * char_w),
+                y=line_y,
+                w=max(1, int(char_w)),
+                h=text_h,
+                conf=95.0,
+            ))
+        cursor_x += word_w
+        if wi < len(words) - 1:
+            space_w = font.getlength(" ")
+            chars.append(OcrChar(
+                text=" ",
+                x=int(cursor_x),
+                y=line_y,
+                w=max(1, int(space_w)),
+                h=text_h,
+                conf=95.0,
+            ))
+            cursor_x += space_w
+
+    line = OcrLine(
+        chars=chars,
+        x=line_x,
+        y=line_y,
+        w=line_w,
+        h=line_h,
+    )
+
+    # Draw a black redaction box covering a fraction of the line
+    redact_x = line_x + int(line_w * redaction_frac[0])
+    redact_y = line_y
+    redact_w = int(line_w * (redaction_frac[1] - redaction_frac[0]))
+    redact_h = line_h
+    draw.rectangle(
+        [redact_x, redact_y, redact_x + redact_w, redact_y + redact_h],
+        fill=0,
+    )
+
+    redaction_boxes = [(redact_x, redact_y, redact_w, redact_h)]
+
+    # Convert to RGB page image (detect_font_masked expects PIL Image)
+    page_rgb = page_img.convert("RGB")
+    return line, page_rgb, redaction_boxes
+
+
+def test_masked_detection_finds_correct_font():
+    """Render TNR@50, add a black redaction box, and verify detection still finds TNR."""
+    text = "On Aug 27 2012 at 12:52 PM wrote ot"
+    line, page_img, redaction_boxes = _render_page_with_redaction(
+        font_name="Times New Roman",
+        font_size=50,
+        text=text,
+    )
+
+    result = detect_font_masked(line, page_img, redaction_boxes)
+
+    assert "Times" in result.font_name or "Liberation Serif" in result.font_name, (
+        f"Expected serif font, got {result.font_name}"
+    )
+    assert 47 <= result.font_size <= 53, (
+        f"Expected size ~50, got {result.font_size}"
+    )
+    assert result.score > 0.3, (
+        f"Expected reasonable score, got {result.score:.3f}"
+    )
+
+
+def test_masked_detection_not_confused_by_redaction():
+    """Render Arial@40, add a black redaction box, and verify it finds Arial."""
+    text = "On Aug 27 2012 at 12:52 PM wrote ot"
+    line, page_img, redaction_boxes = _render_page_with_redaction(
+        font_name="Arial",
+        font_size=40,
+        text=text,
+    )
+
+    result = detect_font_masked(line, page_img, redaction_boxes)
+
+    assert "Arial" in result.font_name or "Liberation Sans" in result.font_name, (
+        f"Expected sans-serif font, got {result.font_name}"
+    )
+    assert 37 <= result.font_size <= 43, (
+        f"Expected size ~40, got {result.font_size}"
+    )
+    assert result.score > 0.3, (
+        f"Expected reasonable score, got {result.score:.3f}"
+    )
diff --git a/unredact/pipeline/font_detect.py b/unredact/pipeline/font_detect.py
index ac1a34f..7e96a80 100644
--- a/unredact/pipeline/font_detect.py
+++ b/unredact/pipeline/font_detect.py
@@ -274,6 +274,62 @@ def detect_font_for_line_from_crop(
     return _fine_search(line, line_crop, best)
 
 
+def detect_font_masked(
+    line: OcrLine,
+    page_image: Image.Image,
+    redaction_boxes: list[tuple[int, int, int, int]],
+) -> FontMatch:
+    """Detect the best font by masking redaction boxes to white before scoring.
+
+    Instead of cropping just the unredacted portion of a line (which loses
+    signal from narrow crops and coordinate mismatches), this masks each
+    redaction box to white (255) in the full line crop. The Dice-based pixel
+    scoring naturally ignores the masked (white) regions since they contain
+    no ink pixels.
+
+    Args:
+        line: OCR line with page-relative coordinates.
+        page_image: Full page as a PIL Image (any mode; converted to grayscale).
+        redaction_boxes: List of (rx, ry, rw, rh) rectangles in page-relative
+            coordinates. Each rectangle is painted white before scoring.
+
+    Returns:
+        FontMatch with the best font name, path, size, and score.
+    """
+    # 1. Crop the line region from the page image
+    line_crop = np.array(
+        page_image.convert("L").crop((line.x, line.y, line.x + line.w, line.y + line.h))
+    )
+
+    # 2. Mask each redaction box to white (255) — convert page-relative to crop-relative
+    for rx, ry, rw, rh in redaction_boxes:
+        # Convert from page coordinates to crop-relative coordinates
+        cx = rx - line.x
+        cy = ry - line.y
+
+        # Clip to the crop bounds
+        x0 = max(0, cx)
+        y0 = max(0, cy)
+        x1 = min(line.w, cx + rw)
+        y1 = min(line.h, cy + rh)
+
+        if x0 < x1 and y0 < y1:
+            line_crop[y0:y1, x0:x1] = 255
+
+    # 3. Create a scoring line with crop-relative coordinates (x=0, y=0)
+    scoring_line = OcrLine(
+        chars=line.chars,
+        x=0, y=0,
+        w=line.w, h=line.h,
+    )
+
+    # 4. Full search then fine search
+    best = _full_search(scoring_line, line_crop)
+    if best is None:
+        raise RuntimeError("No matching font found. Check system fonts.")
+    return _fine_search(scoring_line, line_crop, best)
+
+
 def detect_font_for_line(
     line: OcrLine,
     page_image: Image.Image,