diff --git a/graphify/extract.py b/graphify/extract.py
index 9de0c762..e53ca849 100644
--- a/graphify/extract.py
+++ b/graphify/extract.py
@@ -7,6 +7,7 @@ import json
 import os
 import re
 import sys
+import textwrap
 from collections import Counter
 from dataclasses import dataclass, field
 from pathlib import Path
@@ -1033,6 +1034,23 @@ _SWIFT_CONFIG = LanguageConfig(
 _RATIONALE_PREFIXES = ("# NOTE:", "# IMPORTANT:", "# HACK:", "# WHY:", "# RATIONALE:", "# TODO:", "# FIXME:")
 
 
+def _shorten_rationale_label(text: str, width: int = 80) -> str:
+    """Collapse whitespace and truncate ``text`` to ``width`` chars for a
+    rationale node label, cutting on a word boundary rather than mid-word.
+    Shared by the Python and JS/TS rationale extractors (#2206).
+
+    ``textwrap.shorten`` collapses to just the placeholder when the first
+    "word" alone exceeds ``width`` (e.g. a docstring/comment that opens with
+    an unbroken URL) -- that would emit a content-free label, so fall back to
+    a plain character truncation of the normalized text in that case.
+    """
+    label = textwrap.shorten(text, width=width, placeholder="…")
+    if label in ("", "…"):
+        flat = " ".join(text.split())
+        label = flat if len(flat) <= width else flat[: width - 1] + "…"
+    return label
+
+
 def _is_autogenerated_python(source: bytes) -> bool:
     """Return True if this Python file is auto-generated and its module docstring is noise.
 
@@ -1091,7 +1109,11 @@ def _extract_python_rationale(path: Path, result: dict) -> None:
         return None
 
     def _add_rationale(text: str, line: int, parent_nid: str) -> None:
-        label = text[:80].replace("\r\n", " ").replace("\r", " ").replace("\n", " ").strip()
+        # Normalize whitespace before truncating, not after: slicing raw text
+        # first can land mid-word, leave a run of literal spaces where a
+        # newline + indentation used to be, or end on a "." that turns into
+        # an Obsidian "..md" filename once export.py appends the extension.
+        label = _shorten_rationale_label(text)
         rid = _make_id(stem, "rationale", str(line))
         if rid not in seen_ids:
             seen_ids.add(rid)
@@ -1228,7 +1250,11 @@ def _extract_js_rationale(path: Path, result: dict) -> None:
     seen_doc_refs: set[str] = set()
 
     def _add_rationale(text: str, line: int) -> None:
-        label = text[:80].replace("\r\n", " ").replace("\r", " ").replace("\n", " ").strip()
+        # Normalize whitespace before truncating, not after: slicing raw text
+        # first can land mid-word, leave a run of literal spaces where a
+        # newline + indentation used to be, or end on a "." that turns into
+        # an Obsidian "..md" filename once export.py appends the extension.
+        label = _shorten_rationale_label(text)
         rid = _make_id(stem, "rationale", str(line))
         if rid not in seen_ids:
             seen_ids.add(rid)
diff --git a/tests/test_rationale.py b/tests/test_rationale.py
index 4c915664..bb91d7c0 100644
--- a/tests/test_rationale.py
+++ b/tests/test_rationale.py
@@ -263,6 +263,106 @@ def test_decorated_method_node_id_is_class_qualified(tmp_path):
             )
 
 
+# ── Regression for #2206: labels must normalize whitespace before truncating ──
+
+
+def test_long_docstring_label_truncates_on_word_boundary(tmp_path):
+    """A docstring longer than the 80-char cap must be shortened at a word
+    boundary, not mid-word. Before the fix, ``text[:80]`` sliced "feeds" down
+    to "feed"."""
+    docstring = ("This routine reconciles pending settlement batches nightly "
+                 "because upstream feeds arrive unordered and out of sequence.")
+    path = _write_py(tmp_path, f'''
+        def reconcile_batches():
+            """{docstring}"""
+            pass
+    ''')
+    result = extract_python(path)
+    rationale = [n for n in result["nodes"] if n.get("file_type") == "rationale"]
+    assert len(rationale) == 1
+    label = rationale[0]["label"]
+    assert len(label) <= 80
+    core = label[:-1].rstrip() if label.endswith("…") else label
+    assert docstring.startswith(core)
+    if core != docstring:
+        # Whatever follows the retained prefix in the source must be a space
+        # (or end of string) -- i.e. the cut landed on a word boundary.
+        assert docstring[len(core):len(core) + 1] in (" ", ""), label
+
+
+def test_docstring_newline_and_indentation_collapsed_to_single_space(tmp_path):
+    """A multi-line docstring's line break + indentation must not survive as a
+    run of literal spaces inside the label (the raw slice used to keep them
+    because it ran before the newline-to-space normalization)."""
+    path = _write_py(tmp_path, '''
+        def sync_inventory():
+            """Aggregates daily settlement counts for reconciliation runs.
+               Retries three times before raising to the monitoring pipeline.
+            """
+            pass
+    ''')
+    result = extract_python(path)
+    rationale = [n for n in result["nodes"] if n.get("file_type") == "rationale"]
+    label = rationale[0]["label"]
+    assert "\n" not in label
+    assert "  " not in label, f"whitespace run survived in label: {label!r}"
+    assert "runs. Retries" in label
+
+
+def test_truncated_docstring_never_ends_with_bare_period(tmp_path):
+    """When the old 80-char cut happened to land on a ".", the Obsidian
+    exporter appended ".md" and produced a double-dot filename. A truncated
+    label must end on the placeholder, never on a lone trailing period."""
+    docstring = ("Loads the merchant configs bundle from disk once at process "
+                 "start-up and caches. It refreshes every six hours in the background.")
+    path = _write_py(tmp_path, f'''
+        def load_merchant_config():
+            """{docstring}"""
+            pass
+    ''')
+    result = extract_python(path)
+    rationale = [n for n in result["nodes"] if n.get("file_type") == "rationale"]
+    label = rationale[0]["label"]
+    assert len(label) < len(docstring), "expected this docstring to be truncated"
+    assert not label.endswith("."), label
+    assert label.endswith("…"), label
+
+
+def test_docstring_opening_with_unbroken_long_token_keeps_content(tmp_path):
+    """Adversarial case: ``textwrap.shorten`` alone collapses to just the
+    placeholder when the first whitespace-delimited "word" already exceeds
+    the width (e.g. a docstring opening with a long, unbroken URL) -- that
+    would regress to a content-free label, worse than the original bug. The
+    label must still carry real content."""
+    url = "https://example.com/api/v3/settlements/" + "a" * 60 + "/confirm"
+    docstring = f"{url} documents the retry contract for this handler."
+    path = _write_py(tmp_path, f'''
+        def call_endpoint():
+            """{docstring}"""
+            pass
+    ''')
+    result = extract_python(path)
+    rationale = [n for n in result["nodes"] if n.get("file_type") == "rationale"]
+    label = rationale[0]["label"]
+    assert label not in ("", "…"), label
+    assert label.startswith("https://example.com/"), label
+
+
+def test_short_docstring_label_unchanged(tmp_path):
+    """Non-regression: a docstring well under 80 chars must pass through
+    byte-for-byte, with no placeholder and no reformatting."""
+    docstring = "Splits the bearer token because some clients send a stray prefix."
+    path = _write_py(tmp_path, f'''
+        def parse_token():
+            """{docstring}"""
+            pass
+    ''')
+    result = extract_python(path)
+    rationale = [n for n in result["nodes"] if n.get("file_type") == "rationale"]
+    label = rationale[0]["label"]
+    assert label == docstring
+
+
 # ── JS/TS rationale + doc-reference extraction ────────────────────────────────
 
 
@@ -330,3 +430,80 @@ def test_js_adr_in_string_literal_not_extracted(tmp_path):
     result = extract_js(path)
     refs = [n for n in result["nodes"] if n.get("file_type") == "doc_ref"]
     assert refs == []
+
+
+# ── Regression for #2206, JS/TS site (shares the fix with the Python site) ────
+
+
+def test_js_rationale_label_truncates_on_word_boundary(tmp_path):
+    """Same invariant as the Python site: a long ``// WHY:`` comment must be
+    shortened at a word boundary, not mid-word."""
+    from graphify.extract import extract_js
+    comment_text = ("retries are capped because the upstream billing service "
+                     "enforces a strict per-tenant rate limit that keeps dropping requests")
+    path = _write_ts(tmp_path, f'''
+        // WHY: {comment_text}
+        export function fetchData(): void {{}}
+    ''')
+    result = extract_js(path)
+    rationale = [n for n in result["nodes"] if n.get("file_type") == "rationale"]
+    assert len(rationale) == 1
+    label = rationale[0]["label"]
+    full = f"WHY: {comment_text}"
+    assert len(label) <= 80
+    core = label[:-1].rstrip() if label.endswith("…") else label
+    assert full.startswith(core)
+    if core != full:
+        assert full[len(core):len(core) + 1] in (" ", ""), label
+
+
+def test_js_rationale_label_never_ends_with_bare_period_when_truncated(tmp_path):
+    """Same invariant as the Python site: a truncated label must never end on
+    a lone "." (double-dot Obsidian filename)."""
+    from graphify.extract import extract_js
+    comment_text = ("retries are capped at five attempts before the circuit breaker "
+                     "opens for the endpoint. A metrics counter records every trip.")
+    path = _write_ts(tmp_path, f'''
+        // WHY: {comment_text}
+        export function fetchData(): void {{}}
+    ''')
+    result = extract_js(path)
+    rationale = [n for n in result["nodes"] if n.get("file_type") == "rationale"]
+    label = rationale[0]["label"]
+    full = f"WHY: {comment_text}"
+    assert len(label) < len(full), "expected this comment to be truncated"
+    assert not label.endswith("."), label
+
+
+def test_js_rationale_comment_opening_with_unbroken_long_token_keeps_content(tmp_path):
+    """Same adversarial case as the Python site: a ``// WHY:`` comment whose
+    content is an unbroken long URL must not collapse to a content-free
+    placeholder label. Unlike the Python site, the ``WHY:`` prefix always
+    fits on its own, so the invariant is "some real content survives",
+    not "the URL itself survives" (it genuinely cannot fit in 80 chars)."""
+    from graphify.extract import extract_js
+    url = "https://example.com/api/v3/settlements/" + "a" * 60 + "/confirm"
+    path = _write_ts(tmp_path, f'''
+        // WHY: {url} documents the retry contract for this handler.
+        export function fetchData(): void {{}}
+    ''')
+    result = extract_js(path)
+    rationale = [n for n in result["nodes"] if n.get("file_type") == "rationale"]
+    label = rationale[0]["label"]
+    assert label not in ("", "…"), label
+    assert label.startswith("WHY:"), label
+
+
+def test_js_short_rationale_comment_unchanged(tmp_path):
+    """Non-regression: a short ``// NOTE:`` comment must pass through
+    byte-for-byte, matching the pre-existing test above but pinned exactly."""
+    from graphify.extract import extract_js
+    path = _write_ts(tmp_path, '''
+        // NOTE: must run before compile() or the linker will fail
+        export function build(): void {}
+    ''')
+    result = extract_js(path)
+    rationale = [n for n in result["nodes"] if n.get("file_type") == "rationale"]
+    assert [n["label"] for n in rationale] == [
+        "NOTE: must run before compile() or the linker will fail"
+    ]