diff --git a/CHANGELOG.md b/CHANGELOG.md
index ff6a60af..fea2756c 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -141,6 +141,10 @@ Status of the `main` branch. Changes prior to the next official version change w
     `(int X, string Y)`, had their name corrupted to include a trailing `:` because the
     parenthesis in the type was mistaken for a method's parameter list; `find_symbol` on
     the real name then returned nothing
+  - Fix: TypeScript's `_has_waited_for_cross_file_references` latch was set after the first
+    cross-file query and never reset, so a later query that opened a file from a project tsserver
+    had not loaded yet (e.g. a monorepo package) skipped the indexing wait even while that
+    project's own `$/progress` indexing was still in flight (#1937)
   - Fix: Nextflow's `_flush_deferred_workspace_scan` marked the workspace scan flushed even when both
     of its `completion` probes failed, permanently skipping the flush (and silencing retries) for the
     rest of the session (#1871)
diff --git a/src/solidlsp/language_servers/typescript_language_server.py b/src/solidlsp/language_servers/typescript_language_server.py
index ca293961..e3ae0868 100644
--- a/src/solidlsp/language_servers/typescript_language_server.py
+++ b/src/solidlsp/language_servers/typescript_language_server.py
@@ -575,18 +575,29 @@ class TypeScriptLanguageServer(SolidLanguageServer):
 
     @override
     def _wait_for_cross_file_references_if_needed(self) -> None:
-        if self._has_waited_for_cross_file_references:
+        timeout = self._get_indexing_timeout()
+        if not self._has_waited_for_cross_file_references:
+            start_grace = self._get_indexing_start_grace()
+            self._log_cross_file_indexing_wait_outcome(
+                self._wait_for_indexing_start_or_completion(timeout=timeout, start_grace=start_grace), timeout
+            )
+            self._has_waited_for_cross_file_references = True
             return
 
-        timeout = self._get_indexing_timeout()
-        start_grace = self._get_indexing_start_grace()
-        if self._wait_for_indexing_start_or_completion(timeout=timeout, start_grace=start_grace):
+        # The latch above only covers the first query; a later one can still open a file from a
+        # project tsserver has not loaded before, starting a fresh $/progress cycle to drain.
+        with self._progress_lock:
+            indexing_in_progress = bool(self._active_progress_tokens)
+        if indexing_in_progress:
+            self._log_cross_file_indexing_wait_outcome(self.wait_for_indexing(timeout=timeout), timeout)
+
+    def _log_cross_file_indexing_wait_outcome(self, completed: bool, timeout: float) -> None:
+        if completed:
             log.info("TypeScript cross-file indexing complete")
         else:
             log.warning(
                 "TypeScript cross-file indexing did not complete within %.0fs; proceeding (%s)", timeout, self.describe_indexing_state()
             )
-        self._has_waited_for_cross_file_references = True
 
     @override
     def _get_preferred_definition(self, definitions: list[ls_types.Location]) -> ls_types.Location:
diff --git a/test/solidlsp/test_typescript_timeout_policy.py b/test/solidlsp/test_typescript_timeout_policy.py
index f71867ca..ac6b7128 100644
--- a/test/solidlsp/test_typescript_timeout_policy.py
+++ b/test/solidlsp/test_typescript_timeout_policy.py
@@ -284,6 +284,42 @@ class TestWaitForCrossFileReferencesUsesConfiguredGrace:
         server._wait_for_cross_file_references_if_needed()
         assert time.monotonic() - start < 0.1
 
+    def test_second_call_drains_a_progress_token_already_in_flight(self) -> None:
+        """oraios/serena#1937: a later cross-file query can open a file from a project tsserver
+        has not loaded yet (e.g. a monorepo package), starting a fresh $/progress cycle. The
+        once-only latch must not let that query return while the fresh token is still active.
+        """
+        server = _bare_ts_server(TypeScriptLanguageServer, {"indexing_start_grace": 0.05})
+        server._has_waited_for_cross_file_references = True
+        server._active_progress_tokens.add("tsserver/project-b-load")
+        server._indexing_complete.clear()
+
+        def _drain_shortly() -> None:
+            time.sleep(0.2)
+            with server._progress_lock:
+                server._active_progress_tokens.discard("tsserver/project-b-load")
+                server._indexing_complete.set()
+
+        threading.Thread(target=_drain_shortly, daemon=True).start()
+
+        start = time.monotonic()
+        server._wait_for_cross_file_references_if_needed()
+        elapsed = time.monotonic() - start
+
+        # proves the wait actually blocked for the still-active token, not a fast no-op return
+        assert elapsed >= 0.15
+        assert server._active_progress_tokens == set()
+
+    def test_second_call_proceeds_on_timeout_while_a_token_never_drains(self) -> None:
+        server = _bare_ts_server(TypeScriptLanguageServer, {"indexing_timeout": 0.05})
+        server._has_waited_for_cross_file_references = True
+        server._active_progress_tokens.add("tsserver/project-b-load")
+        server._indexing_complete.clear()
+
+        server._wait_for_cross_file_references_if_needed()  # must log and return, not raise or hang
+
+        assert server._active_progress_tokens == {"tsserver/project-b-load"}
+
 
 class _FakeSolidLSPSettings:
     """Minimal settings stand-in: returns a fixed TypeScript indexing_timeout so the guard tests can