diff --git a/rulechef/executor.py b/rulechef/executor.py
index ecb8b94..0eb57f1 100644
--- a/rulechef/executor.py
+++ b/rulechef/executor.py
@@ -3,6 +3,7 @@
 import json
 import re
 import signal
+import string
 import threading
 from typing import Any
 
@@ -18,6 +19,13 @@
 # bound, one bad rule freezes the whole evaluation loop.
 RULE_TIMEOUT_S = 3.0
 
+# Characters trimmed from the edges of a produced entity span when snapping
+# to word boundaries (see `substitute_template`). Whitespace + standard
+# punctuation, not full Unicode punctuation categories — this only needs to
+# catch the common over-capture cases (trailing comma, wrapping quotes),
+# not act as a general tokenizer.
+_BOUNDARY_TRIM_CHARS = string.whitespace + string.punctuation
+
 
 class _RuleTimeout(Exception):
     pass
@@ -183,6 +191,29 @@ def substitute_template(
             result["start"] = start + offset
             result["end"] = result["start"] + len(result["text"])
 
+    # Snap the span to word boundaries: a regex that over-captures a
+    # trailing/leading punctuation or space mark (e.g. "London," instead of
+    # "London") turns a boundary slip into both a false positive and a false
+    # negative under the default `text` matching mode (see evaluation.py
+    # `_match_entities`). Trim only whitespace/punctuation at the edges —
+    # never touch interior characters — so the produced text lines up with
+    # gold spans without changing what the rule's capture group intended.
+    if (
+        "text" in result
+        and "start" in result
+        and "end" in result
+        and isinstance(result["text"], str)
+        and isinstance(result["start"], int)
+        and isinstance(result["end"], int)
+        and result["text"]
+    ):
+        stripped = result["text"].strip(_BOUNDARY_TRIM_CHARS)
+        if stripped and stripped != result["text"]:
+            lead_trim = len(result["text"]) - len(result["text"].lstrip(_BOUNDARY_TRIM_CHARS))
+            result["start"] += lead_trim
+            result["end"] = result["start"] + len(stripped)
+            result["text"] = stripped
+
     return result
 
 
diff --git a/tests/test_executor.py b/tests/test_executor.py
index 26f28d7..23e33a5 100644
--- a/tests/test_executor.py
+++ b/tests/test_executor.py
@@ -49,6 +49,33 @@ def test_group_zero_via_dollar_zero(self):
         result = substitute_template(tpl, "full_match", 0, 10, groups=())
         assert result == {"match": "full_match"}
 
+    def test_trailing_punctuation_snapped_from_span(self):
+        tpl = {"text": "$0", "start": "$start", "end": "$end"}
+        # "London," at offset 10-17 in some larger text; the rule over-captured
+        # the trailing comma.
+        result = substitute_template(tpl, "London,", 10, 17)
+        assert result == {"text": "London", "start": 10, "end": 16}
+
+    def test_leading_and_trailing_whitespace_snapped_from_span(self):
+        tpl = {"text": "$0", "start": "$start", "end": "$end"}
+        result = substitute_template(tpl, " Paris ", 5, 12)
+        assert result == {"text": "Paris", "start": 6, "end": 11}
+
+    def test_wrapping_quotes_snapped_from_span(self):
+        tpl = {"text": "$0", "start": "$start", "end": "$end"}
+        result = substitute_template(tpl, '"Berlin"', 0, 8)
+        assert result == {"text": "Berlin", "start": 1, "end": 7}
+
+    def test_no_snap_needed_leaves_span_unchanged(self):
+        tpl = {"text": "$0", "start": "$start", "end": "$end"}
+        result = substitute_template(tpl, "Tokyo", 0, 5)
+        assert result == {"text": "Tokyo", "start": 0, "end": 5}
+
+    def test_all_punctuation_text_is_not_snapped_to_empty(self):
+        tpl = {"text": "$0", "start": "$start", "end": "$end"}
+        result = substitute_template(tpl, "---", 0, 3)
+        assert result == {"text": "---", "start": 0, "end": 3}
+
 
 # =========================================================================
 # RuleExecutor._execute_regex_rule
@@ -122,6 +149,26 @@ def test_no_match_returns_empty(self):
         results = self.executor._execute_regex_rule(rule, {"text": "nothing here"})
         assert results == []
 
+    def test_over_captured_trailing_punctuation_is_snapped(self):
+        # A rule that (deliberately, as a stand-in for a real over-broad
+        # LLM-written pattern) captures a trailing comma along with the city
+        # name. Under the default `text` matching mode this boundary slip
+        # would count as both a false positive and a false negative against
+        # a gold span of just "London" (rulechef/evaluation.py:_match_entities).
+        rule = Rule(
+            id="r5",
+            name="city",
+            description="Match a city mention followed by optional punctuation",
+            format=RuleFormat.REGEX,
+            content=r"London,?",
+            output_template={"text": "$0", "start": "$start", "end": "$end"},
+        )
+        text = "She lives in London, near the river."
+        results = self.executor._execute_regex_rule(rule, {"text": text})
+        assert len(results) == 1
+        assert results[0]["text"] == "London"
+        assert text[results[0]["start"] : results[0]["end"]] == "London"
+
 
 # =========================================================================
 # RuleExecutor._execute_code_rule