diff --git a/backend/apps/agents/browser/browser_skills.py b/backend/apps/agents/browser/browser_skills.py
index c4058b0c..06e86328 100644
--- a/backend/apps/agents/browser/browser_skills.py
+++ b/backend/apps/agents/browser/browser_skills.py
@@ -160,7 +160,10 @@ def normalize_task(task: str) -> str:
 # value is filled from the LIVE task at replay (so the value is never stored on
 # disk, a redaction win, and the skill generalizes). Quoting is the explicit,
 # high-precision signal that this token is a parameter; we never guess.
-_QUOTE_RE = re.compile(r'["“”‘’\']([^"“”‘’\']{1,200})["“”‘’\']')
+# Lookarounds keep word-internal apostrophes (chen's, don't) from opening a
+# span; without them every possessive made each task wording a unique sig and
+# silently disabled skill matching for those tasks.
+_QUOTE_RE = re.compile(r'(?<!\w)["“”‘’\']([^"“”‘’\']{1,200})["“”‘’\'](?!\w)')
 _SLOT_TOKEN = " slotvalue "
 
 
diff --git a/backend/tests/test_browser_skills.py b/backend/tests/test_browser_skills.py
index 0ba617cb..5bf03b83 100644
--- a/backend/tests/test_browser_skills.py
+++ b/backend/tests/test_browser_skills.py
@@ -514,3 +514,14 @@ def test_first_unsafe_step_splits_send_skills():
     assert i == 2 and "irreversible" in why
     safe, _ = replay_safety(send_flow)
     assert not safe
+
+
+def test_template_task_ignores_possessive_apostrophes():
+    from backend.apps.agents.browser.browser_skills import template_task, _sig
+    r14 = "go to tyler chen's linkedin hes in entrepreneurs first and text him '[test] hello world r14-os'"
+    r15 = "go to tyler chen's linkedin hes in entrepreneurs first and text him '[test] hello world r15-os'"
+    t14, v14 = template_task(r14)
+    assert v14 == ["[test] hello world r14-os"]
+    assert "chen's linkedin" in t14
+    assert _sig(r14) == _sig(r15)
+    assert template_task("no quotes here at all") == ("no quotes here at all", [])