diff --git a/gateway/run.py b/gateway/run.py
index d26b679b182..99e2d9de9f6 100644
--- a/gateway/run.py
+++ b/gateway/run.py
@@ -16544,6 +16544,37 @@ class GatewayRunner:
                     entry.session_id = agent.session_id
                     self.session_store._save()
 
+                # If this is a Telegram DM and source.thread_id was lost during
+                # the session split (synthetic / recovered event), restore it
+                # from the binding so _thread_metadata_for_source produces the
+                # correct message_thread_id instead of routing to the General
+                # thread.  Failure here is non-fatal — we log and continue;
+                # worst case the message lands in General, which is the
+                # pre-fix behaviour.
+                if (
+                    getattr(source, "platform", None) == Platform.TELEGRAM
+                    and getattr(source, "chat_type", None) == "dm"
+                    and getattr(source, "thread_id", None) is None
+                    and self._session_db is not None
+                ):
+                    try:
+                        _binding = self._session_db.get_telegram_topic_binding_by_session(
+                            session_id=agent.session_id,
+                        )
+                        if _binding and _binding.get("thread_id"):
+                            source.thread_id = str(_binding["thread_id"])
+                            logger.debug(
+                                "Restored source.thread_id=%s from binding after session split %s → %s",
+                                source.thread_id,
+                                session_id,
+                                agent.session_id,
+                            )
+                    except Exception:
+                        logger.debug(
+                            "Failed to restore thread_id from binding after session split",
+                            exc_info=True,
+                        )
+
             effective_session_id = getattr(agent, 'session_id', session_id) if agent else session_id
 
             # When compression created a new session, the messages list was
diff --git a/hermes_state.py b/hermes_state.py
index e984e653be2..e8e8947c05a 100644
--- a/hermes_state.py
+++ b/hermes_state.py
@@ -2852,6 +2852,30 @@ class SessionDB:
                 return []
         return [dict(row) for row in rows]
 
+    def get_telegram_topic_binding_by_session(
+        self,
+        *,
+        session_id: str,
+    ) -> Optional[Dict[str, Any]]:
+        """Return the Telegram DM topic binding for a given session_id, if present.
+
+        Uses the UNIQUE INDEX on telegram_dm_topic_bindings(session_id) for an
+        efficient reverse lookup. Returns None when the session has no binding or
+        the table does not exist yet.
+        """
+        with self._lock:
+            try:
+                row = self._conn.execute(
+                    """
+                    SELECT * FROM telegram_dm_topic_bindings
+                    WHERE session_id = ?
+                    """,
+                    (str(session_id),),
+                ).fetchone()
+            except sqlite3.OperationalError:
+                return None
+        return dict(row) if row else None
+
     def bind_telegram_topic(
         self,
         *,
diff --git a/tests/gateway/test_telegram_topic_mode.py b/tests/gateway/test_telegram_topic_mode.py
index 1a577bfd486..7945fb716b0 100644
--- a/tests/gateway/test_telegram_topic_mode.py
+++ b/tests/gateway/test_telegram_topic_mode.py
@@ -1229,6 +1229,100 @@ def test_list_telegram_topic_bindings_for_chat_no_table(tmp_path):
     assert tables == set()
 
 
+# ---------------------------------------------------------------------------
+# Tests for get_telegram_topic_binding_by_session (issue #27166)
+# ---------------------------------------------------------------------------
+
+def test_get_telegram_topic_binding_by_session_returns_binding(tmp_path):
+    """Reverse lookup by session_id returns the binding row."""
+    db = SessionDB(db_path=tmp_path / "state.db")
+    db.enable_telegram_topic_mode(chat_id="208214988", user_id="208214988")
+    db.create_session(session_id="sess-27166", source="telegram", user_id="208214988")
+    db.bind_telegram_topic(
+        chat_id="208214988",
+        thread_id="17585",
+        user_id="208214988",
+        session_key="agent:main:telegram:dm:208214988:17585",
+        session_id="sess-27166",
+    )
+
+    binding = db.get_telegram_topic_binding_by_session(session_id="sess-27166")
+
+    assert binding is not None
+    assert binding["chat_id"] == "208214988"
+    assert binding["thread_id"] == "17585"
+    assert binding["session_id"] == "sess-27166"
 
 
+def test_get_telegram_topic_binding_by_session_returns_none_for_unknown(tmp_path):
+    """Returns None when no binding exists for the given session_id."""
+    db = SessionDB(db_path=tmp_path / "state.db")
+    db.apply_telegram_topic_migration()
 
+    result = db.get_telegram_topic_binding_by_session(session_id="nonexistent-sess")
+
+    assert result is None
+
+
+# ---------------------------------------------------------------------------
+# Test for session-split thread_id recovery (issue #27166)
+# ---------------------------------------------------------------------------
+
+def test_session_split_restores_source_thread_id_from_binding(tmp_path):
+    """After a session split, source.thread_id is restored from the binding.
+
+    Simulates the case where context compression creates a new session_id and
+    source.thread_id is None (synthetic/recovered event). The recovery block
+    must look up the binding by the new session_id and restore thread_id on
+    source so that _thread_metadata_for_source returns the correct thread.
+    """
+    from gateway.run import GatewayRunner
+    from gateway.config import Platform
+
+    db = SessionDB(db_path=tmp_path / "state.db")
+    db.enable_telegram_topic_mode(chat_id="208214988", user_id="208214988")
+    db.create_session(session_id="sess-split-new", source="telegram", user_id="208214988")
+    db.bind_telegram_topic(
+        chat_id="208214988",
+        thread_id="17585",
+        user_id="208214988",
+        session_key="agent:main:telegram:dm:208214988:17585",
+        session_id="sess-split-new",
+    )
+
+    runner = object.__new__(GatewayRunner)
+    runner._session_db = db
+
+    # Build a source that looks like it came from a synthetic/recovered event:
+    # platform and chat_type match a Telegram DM, but thread_id is None.
+    source = _make_source(thread_id=None)
+    assert source.platform == Platform.TELEGRAM
+    assert source.chat_type == "dm"
+    assert source.thread_id is None
+
+    # Simulate the session-split recovery block logic directly.
+    if (
+        getattr(source, "platform", None) == Platform.TELEGRAM
+        and getattr(source, "chat_type", None) == "dm"
+        and getattr(source, "thread_id", None) is None
+        and runner._session_db is not None
+    ):
+        try:
+            _binding = runner._session_db.get_telegram_topic_binding_by_session(
+                session_id="sess-split-new",
+            )
+            if _binding and _binding.get("thread_id"):
+                source.thread_id = str(_binding["thread_id"])
+        except Exception:
+            pass
+
+    assert source.thread_id == "17585", (
+        "thread_id must be restored from the binding after session split"
+    )
+
+    # Confirm _thread_metadata_for_source now returns non-None.
+    runner.config = _make_runner(session_db=db).config
+    runner.adapters = _make_runner(session_db=db).adapters
+    meta = GatewayRunner._thread_metadata_for_source(runner, source)
+    assert meta is not None
+    assert meta["thread_id"] == "17585"