diff --git a/hermes_state.py b/hermes_state.py
index 68387ede17..2d8a0fd4af 100644
--- a/hermes_state.py
+++ b/hermes_state.py
@@ -1249,10 +1249,37 @@ class SessionDB:
             try:
                 with self._lock:
                     ctx_cursor = self._conn.execute(
-                        """SELECT role, content FROM messages
-                           WHERE session_id = ? AND id >= ? - 1 AND id <= ? + 1
-                           ORDER BY id""",
-                        (match["session_id"], match["id"], match["id"]),
+                        """WITH target AS (
+                               SELECT session_id, timestamp, id
+                               FROM messages
+                               WHERE id = ?
+                           )
+                           SELECT role, content
+                           FROM (
+                               SELECT m.id, m.timestamp, m.role, m.content
+                               FROM messages m
+                               JOIN target t ON t.session_id = m.session_id
+                               WHERE (m.timestamp < t.timestamp)
+                                  OR (m.timestamp = t.timestamp AND m.id < t.id)
+                               ORDER BY m.timestamp DESC, m.id DESC
+                               LIMIT 1
+                           )
+                           UNION ALL
+                           SELECT role, content
+                           FROM messages
+                           WHERE id = ?
+                           UNION ALL
+                           SELECT role, content
+                           FROM (
+                               SELECT m.id, m.timestamp, m.role, m.content
+                               FROM messages m
+                               JOIN target t ON t.session_id = m.session_id
+                               WHERE (m.timestamp > t.timestamp)
+                                  OR (m.timestamp = t.timestamp AND m.id > t.id)
+                               ORDER BY m.timestamp ASC, m.id ASC
+                               LIMIT 1
+                           )""",
+                        (match["id"], match["id"]),
                     )
                     context_msgs = [
                         {"role": r["role"], "content": (r["content"] or "")[:200]}
diff --git a/tests/test_hermes_state.py b/tests/test_hermes_state.py
index 72cf47e076..dfb2445c55 100644
--- a/tests/test_hermes_state.py
+++ b/tests/test_hermes_state.py
@@ -365,6 +365,25 @@ class TestFTS5Search:
         assert isinstance(results[0]["context"], list)
         assert len(results[0]["context"]) > 0
 
+    def test_search_context_uses_session_neighbors_when_ids_are_interleaved(self, db):
+        db.create_session(session_id="s1", source="cli")
+        db.create_session(session_id="s2", source="cli")
+
+        db.append_message("s1", role="user", content="before needle")
+        db.append_message("s2", role="user", content="other session message")
+        db.append_message("s1", role="assistant", content="needle match")
+        db.append_message("s2", role="assistant", content="another other session message")
+        db.append_message("s1", role="user", content="after needle")
+
+        results = db.search_messages('"needle match"')
+        needle_result = next(r for r in results if r["session_id"] == "s1" and "needle match" in r["snippet"])
+
+        assert [msg["content"] for msg in needle_result["context"]] == [
+            "before needle",
+            "needle match",
+            "after needle",
+        ]
+
     def test_search_special_chars_do_not_crash(self, db):
         """FTS5 special characters in queries must not raise OperationalError."""
         db.create_session(session_id="s1", source="cli")