diff --git a/help_processor.py b/help_processor.py
index 1f5d7dd..57bf277 100644
--- a/help_processor.py
+++ b/help_processor.py
@@ -676,25 +676,128 @@ def _render_pdf_image(page, img_info, resolution: int = 150) -> Optional[bytes]:
 
 
 _PDF_LINE_Y_TOL = 3.0
+# Typical word space in these PDFs is ~0.2–0.3em; only merge tighter (or drop-caps).
+_PDF_LETTER_GAP_FRAC = 0.12
+# Bare "1" / "2." / "3)" followed by a capital — TOC/list, not "виж 1 и 2".
+_PDF_LIST_MARK_RE = re.compile(
+    r"(?<!\d)(?<![A-Za-zА-Яа-яЁёІіЇїЄєҐґ])(\d{1,2})([.)])?(?=\s+[A-ZА-ЯЁІЇЄҐ])"
+)
+
+
+def _pdf_word_band(w) -> tuple[float, float]:
+    top = float(w.get("top", 0))
+    bot = float(w.get("bottom", top + float(w.get("size") or 10)))
+    if bot <= top:
+        bot = top + max(float(w.get("size") or 10), 1.0)
+    return top, bot
+
+
+def _pdf_cluster_words_by_y(words: list) -> list[dict]:
+    """Visual lines by Y (and vertical overlap), not PDF stream order."""
+    items = [w for w in words if (w.get("text") or "").strip()]
+    items.sort(key=lambda w: (float(w.get("top", 0)), float(w.get("x0", 0))))
+    lines: list[dict] = []
+    for w in items:
+        top, bot = _pdf_word_band(w)
+        placed = False
+        for line in reversed(lines):
+            overlap = min(bot, line["bot"]) - max(top, line["top"])
+            band = min(bot - top, line["bot"] - line["top"])
+            close = abs(top - line["top"]) <= _PDF_LINE_Y_TOL
+            if close or (band > 0 and overlap >= 0.35 * band):
+                line["words"].append(w)
+                line["top"] = min(line["top"], top)
+                line["bot"] = max(line["bot"], bot)
+                placed = True
+                break
+            # Sorted by top: once this word sits clearly below a line, earlier
+            # lines are even higher.
+            if top > line["bot"] + _PDF_LINE_Y_TOL:
+                break
+        if not placed:
+            lines.append({"top": top, "bot": bot, "words": [w]})
+    lines.sort(key=lambda ln: ln["top"])
+    return lines
+
+
+def _pdf_merge_split_letters(ws: list) -> list[dict]:
+    """Join drop-cap / styled first letters: 'C' + 'orrelation' → 'Correlation'."""
+    ordered = sorted(ws, key=lambda w: float(w.get("x0", 0)))
+    clusters: list[dict] = []
+    for w in ordered:
+        text = (w.get("text") or "").strip()
+        if not text:
+            continue
+        x0 = float(w.get("x0", 0))
+        x1 = float(w.get("x1", x0))
+        size = float(w.get("size") or 10)
+        font = str(w.get("fontname") or "")
+        if not clusters:
+            clusters.append({"text": text, "x1": x1, "size": size, "font": font})
+            continue
+        prev = clusters[-1]
+        gap = x0 - prev["x1"]
+        ref = max(size, prev["size"], 1.0)
+        fonts_differ = bool(prev["font"] and font and prev["font"] != font)
+        sizes_differ = abs(size - prev["size"]) > 0.6
+        drop = (
+            len(prev["text"]) == 1
+            and prev["text"].isalpha()
+            and text[0].islower()
+        )
+        tiny = gap < _PDF_LETTER_GAP_FRAC * ref or gap < 0.8
+        if tiny or (drop and gap < 0.55 * ref and (fonts_differ or sizes_differ or gap < 0.2 * ref)):
+            prev["text"] += text
+            prev["x1"] = max(prev["x1"], x1)
+            prev["size"] = max(prev["size"], size)
+            if font:
+                prev["font"] = font
+        else:
+            clusters.append({"text": text, "x1": x1, "size": size, "font": font})
+    return clusters
+
+
+def _pdf_split_list_text(text: str) -> list[str]:
+    """Break a flattened TOC/list: '... 1 Foo 2 Bar' → one item per line."""
+    text = text.strip()
+    if not text:
+        return []
+    matches = list(_PDF_LIST_MARK_RE.finditer(text))
+    if len(matches) < 2:
+        return [text]
+    nums = [int(m.group(1)) for m in matches]
+    if nums[0] not in (1, 2):
+        return [text]
+    if any(nums[i] != nums[0] + i for i in range(len(nums))):
+        return [text]
+    parts: list[str] = []
+    last = 0
+    for m in matches:
+        if m.start() > last:
+            head = text[last:m.start()].strip()
+            if head:
+                parts.append(head)
+        last = m.start()
+    tail = text[last:].strip()
+    if tail:
+        parts.append(tail)
+    return parts or [text]
 
 
 def _pdf_words_to_lines(words: list) -> list[dict]:
     """Group pdfplumber words into visual lines by Y, then left-to-right."""
-    lines: list[dict] = []
-    for w in words:
-        y = float(w.get("top", 0))
-        if lines and abs(y - lines[-1]["top"]) <= _PDF_LINE_Y_TOL:
-            lines[-1]["words"].append(w)
-        else:
-            lines.append({"top": y, "words": [w]})
     result = []
-    for line in lines:
-        ws = sorted(line["words"], key=lambda ww: float(ww.get("x0", 0)))
-        text = " ".join(ww["text"] for ww in ws).strip()
-        if not text:
+    for line in _pdf_cluster_words_by_y(words):
+        ws = line["words"]
+        tokens = _pdf_merge_split_letters(ws)
+        if not tokens:
+            continue
+        joined = " ".join(t["text"] for t in tokens).strip()
+        if not joined:
             continue
         size = round(float(ws[0].get("size", 10)), 1)
-        result.append({"top": line["top"], "size": size, "text": text})
+        for piece in _pdf_split_list_text(joined):
+            result.append({"top": line["top"], "size": size, "text": piece})
     return result
 
 
@@ -730,7 +833,7 @@ def parse_pdf(path: Path) -> list[Section]:
                     continue
                 img_queue.append((float(im.get("top", 0)), data))
 
-            words = page.extract_words(extra_attrs=["size"])
+            words = page.extract_words(extra_attrs=["size", "fontname"])
             visual_lines = _pdf_words_to_lines(words)
             line_buf, line_size = [], None