diff --git a/cmd/server/main.go b/cmd/server/main.go
index e32b1c5..b695858 100644
--- a/cmd/server/main.go
+++ b/cmd/server/main.go
@@ -64,6 +64,15 @@ func main() {
 	}
 	slog.SetDefault(slog.New(slog.NewTextHandler(os.Stderr, &slog.HandlerOptions{Level: level})))
 
+	// Run one-time migrations (e.g. populate cmu_tail for rhyme support)
+	// before opening the database read-only.
+	if n, err := dictionary.Migrate(*dbPath); err != nil {
+		slog.Error("migration failed", "error", err)
+		os.Exit(1)
+	} else if n > 0 {
+		slog.Info("migration complete", "cmu_tails_populated", n)
+	}
+
 	dict, err := dictionary.NewReadOnly(*dbPath)
 	if err != nil {
 		slog.Error("failed to open dictionary", "error", err)
@@ -87,6 +96,8 @@ func main() {
 	mux.HandleFunc("GET /frequency/batch", handleFrequencyBatch(dict))
 	mux.HandleFunc("GET /pronunciation", handlePronunciation(dict))
 	mux.HandleFunc("GET /etymology", handleEtymology(dict))
+	mux.HandleFunc("GET /difficulty", handleDifficulty(dict))
+	mux.HandleFunc("GET /rhyme", handleRhyme(dict))
 	mux.HandleFunc("GET /health", handleHealth(dict, *dbPath))
 
 	serverStart = time.Now()
@@ -507,6 +518,60 @@ func handleEtymology(dict *dictionary.Dictionary) http.HandlerFunc {
 	}
 }
 
+func handleDifficulty(dict *dictionary.Dictionary) http.HandlerFunc {
+	return func(w http.ResponseWriter, r *http.Request) {
+		word := r.URL.Query().Get("word")
+		lang := r.URL.Query().Get("lang")
+		if word == "" || lang == "" {
+			writeError(w, 400, "bad_request", "word and lang are required")
+			return
+		}
+		if !dictionary.ValidLang(lang) {
+			writeError(w, 400, "bad_request", "unsupported language: "+lang)
+			return
+		}
+
+		diff, err := dict.Difficulty(word, lang)
+		if err != nil {
+			slog.Error("difficulty", "error", err)
+			writeError(w, 500, "internal", "internal error")
+			return
+		}
+		writeJSON(w, 200, map[string]any{
+			"word":       word,
+			"lang":       lang,
+			"difficulty": diff,
+		})
+	}
+}
+
+func handleRhyme(dict *dictionary.Dictionary) http.HandlerFunc {
+	return func(w http.ResponseWriter, r *http.Request) {
+		word := r.URL.Query().Get("word")
+		if word == "" {
+			writeError(w, 400, "bad_request", "word is required")
+			return
+		}
+		limit := 10
+		if v := r.URL.Query().Get("limit"); v != "" {
+			if n, err := strconv.Atoi(v); err == nil && n > 0 {
+				limit = n
+			}
+		}
+
+		rhymes, err := dict.Rhymes(word, limit)
+		if err != nil {
+			slog.Error("rhyme", "error", err)
+			writeError(w, 500, "internal", "internal error")
+			return
+		}
+		writeJSON(w, 200, map[string]any{
+			"word":   word,
+			"rhymes": rhymes,
+		})
+	}
+}
+
 func handleHealth(dict *dictionary.Dictionary, dbPath string) http.HandlerFunc {
 	// The database is read-only at runtime, so cache the health response
 	// after the first (slow) computation.
diff --git a/internal/dictionary/db.go b/internal/dictionary/db.go
index 211162a..ff5da72 100644
--- a/internal/dictionary/db.go
+++ b/internal/dictionary/db.go
@@ -157,6 +157,7 @@ func BootstrapSchema(db *sql.DB) error {
 	// when we catch the "duplicate column" error.
 	migrations := []string{
 		"ALTER TABLE words ADD COLUMN difficulty REAL DEFAULT NULL",
+		"ALTER TABLE pronunciations ADD COLUMN cmu_tail TEXT",
 	}
 	for _, m := range migrations {
 		if _, err := db.Exec(m); err != nil {
@@ -170,6 +171,109 @@ func BootstrapSchema(db *sql.DB) error {
 	return nil
 }
 
+// Migrate opens the database read-write, applies any pending schema migrations,
+// and populates derived data (e.g. CMU rhyme tails). Returns the number of
+// CMU tails populated (0 if already up to date).
+func Migrate(dbPath string) (int, error) {
+	db, err := openDB(dbPath)
+	if err != nil {
+		return 0, err
+	}
+	defer db.Close()
+
+	if err := BootstrapSchema(db); err != nil {
+		return 0, err
+	}
+
+	return PopulateCMUTails(db)
+}
+
 func isDuplicateColumn(err error) bool {
 	return err != nil && strings.Contains(err.Error(), "duplicate column")
 }
+
+// PopulateCMUTails computes the rhyme tail for all CMU pronunciation entries
+// that don't already have one. The tail is the phoneme sequence from the last
+// stressed vowel onward (e.g. "K AE1 T" → "AE1 T").
+func PopulateCMUTails(db *sql.DB) (int, error) {
+	// Create index if it doesn't exist.
+	db.Exec("CREATE INDEX IF NOT EXISTS idx_pronunciations_cmu_tail ON pronunciations(cmu_tail)")
+
+	rows, err := db.Query(
+		`SELECT id, value FROM pronunciations WHERE format = 'cmu' AND (cmu_tail IS NULL OR cmu_tail = '')`)
+	if err != nil {
+		return 0, fmt.Errorf("dictionary: populate cmu tails: %w", err)
+	}
+
+	type entry struct {
+		id    int
+		value string
+	}
+	var entries []entry
+	for rows.Next() {
+		var e entry
+		if err := rows.Scan(&e.id, &e.value); err != nil {
+			rows.Close()
+			return 0, fmt.Errorf("dictionary: populate cmu tails scan: %w", err)
+		}
+		entries = append(entries, e)
+	}
+	rows.Close()
+
+	if len(entries) == 0 {
+		return 0, nil
+	}
+
+	tx, err := db.Begin()
+	if err != nil {
+		return 0, fmt.Errorf("dictionary: populate cmu tails begin: %w", err)
+	}
+	defer tx.Rollback()
+
+	stmt, err := tx.Prepare("UPDATE pronunciations SET cmu_tail = ? WHERE id = ?")
+	if err != nil {
+		return 0, fmt.Errorf("dictionary: populate cmu tails prepare: %w", err)
+	}
+	defer stmt.Close()
+
+	count := 0
+	for _, e := range entries {
+		tail := cmuTail(e.value)
+		if tail == "" {
+			continue
+		}
+		if _, err := stmt.Exec(tail, e.id); err != nil {
+			return 0, fmt.Errorf("dictionary: populate cmu tails update: %w", err)
+		}
+		count++
+	}
+
+	if err := tx.Commit(); err != nil {
+		return 0, fmt.Errorf("dictionary: populate cmu tails commit: %w", err)
+	}
+	return count, nil
+}
+
+// cmuTail extracts the phoneme sequence from the last stressed vowel onward.
+// e.g. "K AE1 T" → "AE1 T", "IH0 F EH1 M ER0 AH0 L" → "EH1 M ER0 AH0 L"
+func cmuTail(phonemes string) string {
+	parts := strings.Fields(phonemes)
+	lastStressed := -1
+	for i, p := range parts {
+		if len(p) >= 2 && p[len(p)-1] == '1' {
+			lastStressed = i
+		}
+	}
+	// Fall back to last vowel with any stress marker.
+	if lastStressed == -1 {
+		for i, p := range parts {
+			if len(p) >= 2 && (p[len(p)-1] == '0' || p[len(p)-1] == '2') {
+				lastStressed = i
+			}
+		}
+	}
+	if lastStressed == -1 {
+		return ""
+	}
+	return strings.Join(parts[lastStressed:], " ")
+}
diff --git a/internal/dictionary/query.go b/internal/dictionary/query.go
index ff64001..3ad4fe2 100644
--- a/internal/dictionary/query.go
+++ b/internal/dictionary/query.go
@@ -379,6 +379,82 @@ func (d *Dictionary) Etymology(word, lang string) (string, error) {
 	return text, nil
 }
 
+// Difficulty returns the difficulty score for a word in a language.
+// Returns -1 if the word is not found.
+func (d *Dictionary) Difficulty(word, lang string) (float64, error) {
+	var diff sql.NullFloat64
+	err := d.db.QueryRow(
+		"SELECT difficulty FROM words WHERE word = ? AND lang = ?",
+		strings.ToLower(word), lang,
+	).Scan(&diff)
+	if err == sql.ErrNoRows {
+		return -1, nil
+	}
+	if err != nil {
+		return 0, fmt.Errorf("dictionary: difficulty: %w", err)
+	}
+	if !diff.Valid {
+		return -1, nil
+	}
+	return diff.Float64, nil
+}
+
+// Rhymes returns words that rhyme with the given word by matching CMU phoneme tails.
+// English only. Returns up to `limit` results sorted by frequency descending.
+func (d *Dictionary) Rhymes(word string, limit int) ([]string, error) {
+	if limit <= 0 {
+		limit = 10
+	}
+	if limit > 50 {
+		limit = 50
+	}
+
+	// Get the CMU tail for the input word.
+	var tail sql.NullString
+	err := d.db.QueryRow(`
+		SELECT p.cmu_tail
+		FROM pronunciations p
+		JOIN words w ON w.id = p.word_id
+		WHERE w.word = ? AND w.lang = 'en' AND p.format = 'cmu' AND p.cmu_tail IS NOT NULL
+		LIMIT 1`,
+		strings.ToLower(word),
+	).Scan(&tail)
+	if err == sql.ErrNoRows || !tail.Valid || tail.String == "" {
+		return []string{}, nil
+	}
+	if err != nil {
+		return nil, fmt.Errorf("dictionary: rhymes: %w", err)
+	}
+
+	// Find other words with the same tail.
+	rows, err := d.db.Query(`
+		SELECT DISTINCT w.word
+		FROM pronunciations p
+		JOIN words w ON w.id = p.word_id
+		WHERE p.cmu_tail = ? AND p.format = 'cmu' AND w.lang = 'en' AND w.word != ?
+		ORDER BY w.frequency DESC
+		LIMIT ?`,
+		tail.String, strings.ToLower(word), limit,
+	)
+	if err != nil {
+		return nil, fmt.Errorf("dictionary: rhymes: %w", err)
+	}
+	defer rows.Close()
+
+	var rhymes []string
+	for rows.Next() {
+		var r string
+		if err := rows.Scan(&r); err != nil {
+			return nil, fmt.Errorf("dictionary: rhymes scan: %w", err)
+		}
+		rhymes = append(rhymes, r)
+	}
+	if rhymes == nil {
+		rhymes = []string{}
+	}
+	return rhymes, rows.Err()
+}
+
 func (d *Dictionary) DefCount() (map[string]int, error) {
 	rows, err := d.db.Query(`
 		SELECT w.lang, COUNT(*)