diff --git a/hermes_state.py b/hermes_state.py
index af74ed6f..5a38e73f 100644
--- a/hermes_state.py
+++ b/hermes_state.py
@@ -1035,7 +1035,13 @@ class SessionDB:
         sanitized = re.sub(r"(?i)^(AND|OR|NOT)\b\s*", "", sanitized.strip())
         sanitized = re.sub(r"(?i)\s+(AND|OR|NOT)\s*$", "", sanitized.strip())
 
-        # Step 5: Wrap unquoted hyphenated terms (e.g. ``chat-send``) in
+        # Step 5: Wrap unquoted dotted terms (e.g. ``P2.2``, ``simulate.p2.test.ts``)
+        # in double quotes. In practice, FTS5 query parsing can treat dots as
+        # syntax boundaries, which may produce OperationalError or zero results.
+        # Quoting forces phrase semantics and avoids query parse edge cases.
+        sanitized = re.sub(r"\b([\w-]+(?:\.[\w-]+)+)\b", r'"\1"', sanitized)
+
+        # Step 6: Wrap unquoted hyphenated terms (e.g. ``chat-send``) in
         # double quotes.  FTS5's tokenizer splits on hyphens, turning
         # ``chat-send`` into ``chat AND send``.  Quoting preserves the
         # intended phrase match.
diff --git a/tests/test_hermes_state.py b/tests/test_hermes_state.py
index e79c7f4f..f38d9701 100644
--- a/tests/test_hermes_state.py
+++ b/tests/test_hermes_state.py
@@ -376,6 +376,20 @@ class TestFTS5Search:
         assert any("chat-send" in (r.get("snippet") or r.get("content", "")).lower()
                     for r in results)
 
+    def test_search_dotted_term_does_not_crash(self, db):
+        """Dotted terms like 'P2.2' or 'simulate.p2.test.ts' should not crash FTS5."""
+        db.create_session(session_id="s1", source="cli")
+        db.append_message("s1", role="user", content="Working on P2.2 session_search edge cases")
+        db.append_message("s1", role="assistant", content="See simulate.p2.test.ts for details")
+
+        results = db.search_messages("P2.2")
+        assert isinstance(results, list)
+        assert len(results) >= 1
+
+        results2 = db.search_messages("simulate.p2.test.ts")
+        assert isinstance(results2, list)
+        assert len(results2) >= 1
+
     def test_search_quoted_phrase_preserved(self, db):
         """User-provided quoted phrases should be preserved for exact matching."""
         db.create_session(session_id="s1", source="cli")
@@ -443,6 +457,23 @@ class TestFTS5Search:
         # Hyphenated inside a quoted phrase stays as-is
         assert s('"my chat-send thing"') == '"my chat-send thing"'
 
+    def test_sanitize_fts5_quotes_dotted_terms(self):
+        """Dotted terms should be wrapped in quotes to avoid FTS5 query parse edge cases."""
+        from hermes_state import SessionDB
+        s = SessionDB._sanitize_fts5_query
+
+        assert s('P2.2') == '"P2.2"'
+        assert s('simulate.p2') == '"simulate.p2"'
+        assert s('simulate.p2.test.ts') == '"simulate.p2.test.ts"'
+
+        # Already quoted — no double quoting
+        assert s('"P2.2"') == '"P2.2"'
+
+        # Works with boolean syntax
+        result = s('P2.2 OR simulate.p2')
+        assert '"P2.2"' in result
+        assert '"simulate.p2"' in result
+
 
 # =========================================================================
 # Session search and listing