diff --git a/sentence_difficulty.py b/sentence_difficulty.py
new file mode 100644
index 0000000..829430c
--- /dev/null
+++ b/sentence_difficulty.py
@@ -0,0 +1,198 @@
+"""Sentence difficulty scoring by context-word frequency.
+
+Scores sentences by the median frequency rank of context words
+(excluding the cloze target). Lower score = easier sentence.
+Used by epub_examples.py to select the best cloze sentence.
+"""
+
+from __future__ import annotations
+
+from statistics import median
+
+import helpers
+import nikkud_to_ktiv_male
+
+DEFAULT_RANK = 50_000
+
+# Hebrew prefix consonants for ktiv_male prefix stripping (tier 5)
+_KM_PREFIX_CHARS = set("בהוכלמשע")
+
+# Punctuation to strip from tokens
+_PUNCT = set('.,!?;:"\'"״׳–—()[]{}')
+
+# Maqaf (Hebrew hyphen) — splits tokens
+_MAQAF = "־"
+
+
+def build_nikkud_map(words: dict) -> dict[str, str]:
+    """Build nikkud→ktiv_male lookup from words.json.
+
+    Indexes: headwords, conjugation forms (active, passive, infinitive,
+    reference_form), noun inflections (singular, plural, construct,
+    pronominal suffixes), and adjective inflections (ms/fs/mp/fp).
+
+    Args:
+        words: The full words.json dict keyed by unique_key.
+
+    Returns:
+        Dict mapping nikkud form to ktiv_male string.
+        When collisions occur, last-write wins (acceptable for frequency lookup).
+    """
+    nmap: dict[str, str] = {}
+
+    def _add(nikkud: str | None, ktiv_male: str | None) -> None:
+        if nikkud and ktiv_male:
+            nmap[nikkud] = ktiv_male
+
+    for entry in words.values():
+        word = entry.get("word") or {}
+        _add(word.get("nikkud"), word.get("ktiv_male"))
+
+        # Conjugation forms
+        conj = entry.get("conjugation") or {}
+        for form_entry in conj.get("active_forms") or []:
+            form = form_entry.get("form") or {}
+            _add(form.get("nikkud"), form.get("ktiv_male"))
+        for form_entry in conj.get("hufal_pual_forms") or []:
+            form = form_entry.get("form") or {}
+            _add(form.get("nikkud"), form.get("ktiv_male"))
+        inf = conj.get("infinitive") or {}
+        _add(inf.get("nikkud"), inf.get("ktiv_male"))
+        ref = conj.get("reference_form") or {}
+        _add(ref.get("nikkud"), ref.get("ktiv_male"))
+
+        # Noun inflection forms
+        noun = entry.get("noun_inflection") or {}
+        for field in ("singular", "plural", "construct_singular", "construct_plural"):
+            sub = noun.get(field) or {}
+            nikkud_form = sub.get("nikkud")
+            ktiv = sub.get("ktiv_male")
+            _add(nikkud_form, ktiv)
+            # Index construct forms without maqaf
+            if nikkud_form and nikkud_form.endswith("־") and ktiv:
+                _add(nikkud_form[:-1], ktiv)
+        pronominal = noun.get("pronominal_suffixes") or {}
+        for sub in pronominal.values():
+            if isinstance(sub, dict):
+                _add(sub.get("nikkud"), sub.get("ktiv_male"))
+
+        # Adjective inflection forms
+        adj = entry.get("adjective_inflection") or {}
+        for field in ("ms", "fs", "mp", "fp"):
+            sub = adj.get(field) or {}
+            _add(sub.get("nikkud"), sub.get("ktiv_male"))
+
+    return nmap
+
+
+def _resolve_token_frequency(
+    token: str,
+    nikkud_map: dict[str, str],
+    nikkud_index: dict,
+    freq_data: dict[str, int],
+) -> int:
+    """Resolve a nikkud sentence token to its frequency rank.
+
+    Uses a 5-tier pipeline:
+    1. Known mapping (nikkud_map from words.json)
+    2. Nikkud prefix stripping (epub_examples.try_strip_prefix)
+    3. Academy rules converter (nikkud_to_ktiv_male.convert)
+    4. strip_nikkud fallback (helpers.strip_nikkud)
+    5. Ktiv_male prefix stripping on the converted form
+
+    Returns:
+        Frequency rank (1 = most common). DEFAULT_RANK (50000) if not found.
+    """
+    # Tier 1: Direct lookup in nikkud→ktiv_male map
+    ktiv = nikkud_map.get(token)
+    if ktiv and ktiv in freq_data:
+        return freq_data[ktiv]
+
+    # Tier 2: Nikkud prefix stripping → resolve remainder via nikkud_map
+    from epub_examples import try_strip_prefix
+
+    prefix_hits = try_strip_prefix(token, nikkud_index)
+    for _unique_key, _match_type, matched_remainder in prefix_hits:
+        remainder_ktiv = nikkud_map.get(matched_remainder)
+        if remainder_ktiv and remainder_ktiv in freq_data:
+            return freq_data[remainder_ktiv]
+
+    # Tier 3: Academy rules converter
+    converted = nikkud_to_ktiv_male.convert(token)
+    if converted in freq_data:
+        return freq_data[converted]
+
+    # Tier 4: strip_nikkud fallback
+    stripped = helpers.strip_nikkud(token)
+    if stripped != converted and stripped in freq_data:
+        return freq_data[stripped]
+
+    # Tier 5: Ktiv_male prefix stripping on converted/stripped form
+    for form in (converted, stripped):
+        for prefix_len in (1, 2):
+            if len(form) > prefix_len + 1:
+                prefix = form[:prefix_len]
+                if all(c in _KM_PREFIX_CHARS for c in prefix):
+                    stem = form[prefix_len:]
+                    if stem in freq_data:
+                        return freq_data[stem]
+
+    return DEFAULT_RANK
+
+
+def score_sentence(
+    text: str,
+    target_start: int,
+    target_end: int,
+    nikkud_map: dict[str, str],
+    nikkud_index: dict,
+    freq_data: dict[str, int],
+) -> int:
+    """Score a sentence by median frequency rank of context words.
+
+    Args:
+        text: The full sentence text (with nikkud).
+        target_start: Character offset where the cloze target word starts.
+        target_end: Character offset where the cloze target word ends.
+        nikkud_map: nikkud→ktiv_male mapping from build_nikkud_map().
+        nikkud_index: nikkud index from epub_examples._build_nikkud_index().
+        freq_data: Frequency dict from frequency_lookup.get_freq_data().
+
+    Returns:
+        Median frequency rank of context tokens (int). Lower = easier.
+        Returns DEFAULT_RANK if no scoreable context tokens.
+    """
+    # Tokenize: split on whitespace, then split on maqaf
+    raw_tokens = text.split()
+    tokens_with_pos: list[tuple[str, int, int]] = []
+    pos = 0
+    for raw in raw_tokens:
+        start = text.index(raw, pos)
+        # Split on maqaf
+        parts = raw.split(_MAQAF)
+        sub_pos = start
+        for part in parts:
+            if part:
+                tokens_with_pos.append((part, sub_pos, sub_pos + len(part)))
+            sub_pos += len(part) + 1  # +1 for maqaf
+        pos = start + len(raw)
+
+    # Filter: exclude target word, strip punctuation, skip short tokens
+    context_ranks: list[int] = []
+    for token, tok_start, tok_end in tokens_with_pos:
+        # Exclude target word by overlap with char offsets
+        if tok_start < target_end and tok_end > target_start:
+            continue
+
+        # Strip punctuation from edges
+        cleaned = token.strip("".join(_PUNCT))
+        if len(cleaned) < 2:
+            continue
+
+        rank = _resolve_token_frequency(cleaned, nikkud_map, nikkud_index, freq_data)
+        context_ranks.append(rank)
+
+    if not context_ranks:
+        return DEFAULT_RANK
+
+    return int(median(context_ranks))
diff --git a/tests/test_sentence_difficulty.py b/tests/test_sentence_difficulty.py
new file mode 100644
index 0000000..6b6577b
--- /dev/null
+++ b/tests/test_sentence_difficulty.py
@@ -0,0 +1,207 @@
+"""Tests for sentence difficulty scoring."""
+
+import json
+from pathlib import Path
+
+import pytest
+
+import frequency_lookup
+from sentence_difficulty import DEFAULT_RANK, _resolve_token_frequency, build_nikkud_map, score_sentence
+
+
+class TestBuildNikkudMap:
+    def test_maps_direct_headwords(self):
+        words = {"אָב": {"word": {"nikkud": "אָב", "ktiv_male": "אב"}}}
+        nmap = build_nikkud_map(words)
+        assert nmap["אָב"] == "אב"
+
+    def test_maps_conjugation_forms(self):
+        words = {
+            "שָׁמַר": {
+                "word": {"nikkud": "שָׁמַר", "ktiv_male": "שמר"},
+                "conjugation": {
+                    "active_forms": [
+                        {
+                            "person": "1s",
+                            "tense": "עָבָר",
+                            "form": {"nikkud": "שָׁמַרְתִּי", "ktiv_male": "שמרתי"},
+                        },
+                    ],
+                    "infinitive": {"nikkud": "לִשְׁמֹר", "ktiv_male": "לשמור"},
+                    "reference_form": {"nikkud": "שָׁמַר", "ktiv_male": "שמר"},
+                },
+            }
+        }
+        nmap = build_nikkud_map(words)
+        assert nmap["שָׁמַרְתִּי"] == "שמרתי"
+        assert nmap["לִשְׁמֹר"] == "לשמור"
+
+    def test_maps_noun_inflections(self):
+        words = {
+            "אָב": {
+                "word": {"nikkud": "אָב", "ktiv_male": "אב"},
+                "noun_inflection": {
+                    "singular": {"nikkud": "אָב", "ktiv_male": "אב"},
+                    "plural": {"nikkud": "אָבוֹת", "ktiv_male": "אבות"},
+                    "pronominal_suffixes": {"1s": {"nikkud": "אָבִי", "ktiv_male": "אבי"}},
+                },
+            }
+        }
+        nmap = build_nikkud_map(words)
+        assert nmap["אָבוֹת"] == "אבות"
+        assert nmap["אָבִי"] == "אבי"
+
+    def test_maps_adjective_inflections(self):
+        words = {
+            "גָּדוֹל": {
+                "word": {"nikkud": "גָּדוֹל", "ktiv_male": "גדול"},
+                "adjective_inflection": {
+                    "ms": {"nikkud": "גָּדוֹל", "ktiv_male": "גדול"},
+                    "fs": {"nikkud": "גְּדוֹלָה", "ktiv_male": "גדולה"},
+                    "mp": {"nikkud": "גְּדוֹלִים", "ktiv_male": "גדולים"},
+                    "fp": {"nikkud": "גְּדוֹלוֹת", "ktiv_male": "גדולות"},
+                },
+            }
+        }
+        nmap = build_nikkud_map(words)
+        assert nmap["גְּדוֹלָה"] == "גדולה"
+        assert nmap["גְּדוֹלִים"] == "גדולים"
+
+    def test_construct_forms_strip_maqaf(self):
+        words = {
+            "בֵּית": {
+                "word": {"nikkud": "בֵּית", "ktiv_male": "בית"},
+                "noun_inflection": {
+                    "construct_singular": {"nikkud": "בֵּית־", "ktiv_male": "בית"},
+                },
+            }
+        }
+        nmap = build_nikkud_map(words)
+        assert "בֵּית־" in nmap
+        assert "בֵּית" in nmap
+
+    def test_handles_missing_fields(self):
+        words = {
+            "test": {
+                "word": {"nikkud": "טֶסְט", "ktiv_male": "טסט"},
+                "conjugation": None,
+                "noun_inflection": None,
+                "adjective_inflection": None,
+            }
+        }
+        nmap = build_nikkud_map(words)
+        assert nmap["טֶסְט"] == "טסט"
+
+    def test_real_words_json_coverage(self):
+        words_path = Path(__file__).parent.parent / "data" / "words.json"
+        if not words_path.exists():
+            pytest.skip("words.json not available")
+        with open(words_path, encoding="utf-8") as f:
+            words = json.load(f)
+        nmap = build_nikkud_map(words)
+        assert len(nmap) > 90_000
+
+
+class TestResolveTokenFrequency:
+    @pytest.fixture()
+    def freq_setup(self):
+        frequency_lookup.load()
+        freq_data = frequency_lookup.get_freq_data()
+        words_path = Path(__file__).parent.parent / "data" / "words.json"
+        if not words_path.exists():
+            pytest.skip("words.json not available")
+        with open(words_path, encoding="utf-8") as f:
+            words = json.load(f)
+        from epub_examples import _build_nikkud_index
+
+        nikkud_map = build_nikkud_map(words)
+        nikkud_index = _build_nikkud_index(words)
+        return nikkud_map, nikkud_index, freq_data
+
+    def test_tier1_known_mapping(self, freq_setup):
+        nikkud_map, nikkud_index, freq_data = freq_setup
+        rank = _resolve_token_frequency("אָב", nikkud_map, nikkud_index, freq_data)
+        assert rank is not None
+        assert rank < 50_000
+
+    def test_tier3_academy_converter(self, freq_setup):
+        nikkud_map, nikkud_index, freq_data = freq_setup
+        rank = _resolve_token_frequency("שָׁלוֹם", nikkud_map, nikkud_index, freq_data)
+        assert rank is not None
+        assert rank < 1000
+
+    def test_unknown_token_returns_default(self, freq_setup):
+        nikkud_map, nikkud_index, freq_data = freq_setup
+        rank = _resolve_token_frequency("קְסַנְתּוֹפּוּלוֹס", nikkud_map, nikkud_index, freq_data)
+        assert rank == 50_000
+
+    def test_tier5_ktiv_male_prefix_strip(self, freq_setup):
+        nikkud_map, nikkud_index, freq_data = freq_setup
+        assert freq_data.get("שלום") is not None
+
+
+class TestScoreSentence:
+    @pytest.fixture()
+    def scoring_setup(self):
+        frequency_lookup.load()
+        freq_data = frequency_lookup.get_freq_data()
+        words_path = Path(__file__).parent.parent / "data" / "words.json"
+        if not words_path.exists():
+            pytest.skip("words.json not available")
+        with open(words_path, encoding="utf-8") as f:
+            words = json.load(f)
+        from epub_examples import _build_nikkud_index
+
+        nikkud_map = build_nikkud_map(words)
+        nikkud_index = _build_nikkud_index(words)
+        return nikkud_map, nikkud_index, freq_data
+
+    def test_returns_integer(self, scoring_setup):
+        nmap, nidx, freq = scoring_setup
+        text = "הוּא הָלַךְ הַבַּיְתָה"
+        start = text.index("הָלַךְ")
+        end = start + len("הָלַךְ")
+        score = score_sentence(text, start, end, nmap, nidx, freq)
+        assert isinstance(score, int)
+
+    def test_easy_sentence_scores_lower(self, scoring_setup):
+        nmap, nidx, freq = scoring_setup
+        easy = "הוּא אָמַר שָׁלוֹם"
+        easy_start = easy.index("אָמַר")
+        easy_end = easy_start + len("אָמַר")
+        hard = "הַפַּרְדֵּס נִשְׁתַּטֵּחַ בַּדַּהֲרָה"
+        hard_start = hard.index("נִשְׁתַּטֵּחַ")
+        hard_end = hard_start + len("נִשְׁתַּטֵּחַ")
+        easy_score = score_sentence(easy, easy_start, easy_end, nmap, nidx, freq)
+        hard_score = score_sentence(hard, hard_start, hard_end, nmap, nidx, freq)
+        assert easy_score < hard_score
+
+    def test_single_context_token(self, scoring_setup):
+        nmap, nidx, freq = scoring_setup
+        text = "הוּא טוֹב"
+        start = 0
+        end = len("הוּא")
+        score = score_sentence(text, start, end, nmap, nidx, freq)
+        assert isinstance(score, int)
+
+    def test_handles_punctuation(self, scoring_setup):
+        nmap, nidx, freq = scoring_setup
+        text = '"הוּא טוֹב!"'
+        start = text.index("טוֹב")
+        end = start + len("טוֹב")
+        score = score_sentence(text, start, end, nmap, nidx, freq)
+        assert isinstance(score, int)
+
+    def test_splits_on_maqaf(self, scoring_setup):
+        nmap, nidx, freq = scoring_setup
+        text = "בֵּית־סֵפֶר גָּדוֹל"
+        start = text.index("גָּדוֹל")
+        end = start + len("גָּדוֹל")
+        score = score_sentence(text, start, end, nmap, nidx, freq)
+        assert isinstance(score, int)
+
+    def test_no_context_tokens_returns_default(self, scoring_setup):
+        nmap, nidx, freq = scoring_setup
+        text = "א ב"
+        score = score_sentence(text, 0, 1, nmap, nidx, freq)
+        assert score == DEFAULT_RANK