diff --git a/pylsp/plugins/_rope_task_handle.py b/pylsp/plugins/_rope_task_handle.py
index 7854bb22..ed93a058 100644
--- a/pylsp/plugins/_rope_task_handle.py
+++ b/pylsp/plugins/_rope_task_handle.py
@@ -76,7 +76,9 @@ def __init__(self, workspace: Workspace):
         self.observers = []
 
     def create_jobset(self, name="JobSet", count: Optional[int] = None):
-        report_iter = self.workspace.report_progress(name, None, None)
+        report_iter = self.workspace.report_progress(
+            name, None, None, skip_token_initialization=True
+        )
         result = PylspJobSet(count, report_iter)
         self.job_sets.append(result)
         self._inform_observers()
diff --git a/pylsp/workspace.py b/pylsp/workspace.py
index ea7f55e8..61955cbc 100644
--- a/pylsp/workspace.py
+++ b/pylsp/workspace.py
@@ -135,7 +135,20 @@ def report_progress(
         title: str,
         message: Optional[str] = None,
         percentage: Optional[int] = None,
+        skip_token_initialization: bool = False,
     ) -> Generator[Callable[[str, Optional[int]], None], None, None]:
+        """
+        Report progress to the editor / client.
+
+        ``skip_token_initialization` is necessary due to some current
+        limitations of our LSP implementation. When `report_progress`
+        is used from a synchronous LSP handler, the token initialization
+        will time out because we can't receive the response.
+
+        Many editors will still correctly show the progress messages though, which
+        is why we are giving progress users the option to skip the initialization
+        of the progress token.
+        """
         if self._config:
             client_supports_progress_reporting = (
                 self._config.capabilities.get("window", {}).get("workDoneProgress", False)
@@ -144,30 +157,21 @@ def report_progress(
             client_supports_progress_reporting = False
 
         if client_supports_progress_reporting:
-            try:
-                token = self._progress_begin(title, message, percentage)
-            except Exception:  # pylint: disable=broad-exception-caught
-                log.warning(
-                    "There was an error while trying to initialize progress reporting."
-                    "Likely progress reporting was used in a synchronous LSP handler, "
-                    "which is not supported by progress reporting yet.",
-                    exc_info=True
-                )
+            token = self._progress_begin(title, message, percentage, skip_token_initialization)
 
-            else:
-                def progress_message(message: str, percentage: Optional[int] = None) -> None:
-                    self._progress_report(token, message, percentage)
+            def progress_message(message: str, percentage: Optional[int] = None) -> None:
+                self._progress_report(token, message, percentage)
 
-                try:
-                    yield progress_message
-                finally:
-                    self._progress_end(token)
+            try:
+                yield progress_message
+            finally:
+                self._progress_end(token)
 
-                return
+            return
 
         # FALLBACK:
-        # If the client doesn't support progress reporting, or if we failed to
-        # initialize it, we have a dummy method for the caller to use.
+        # If the client doesn't support progress reporting, we have a dummy method
+        # for the caller to use.
         def dummy_progress_message(message: str, percentage: Optional[int] = None) -> None:
             # pylint: disable=unused-argument
             pass
@@ -179,10 +183,23 @@ def _progress_begin(
         title: str,
         message: Optional[str] = None,
         percentage: Optional[int] = None,
+        skip_token_initialization: bool = False,
     ) -> str:
         token = str(uuid.uuid4())
 
-        self._endpoint.request(self.M_INITIALIZE_PROGRESS, {'token': token}).result(timeout=1.0)
+        if not skip_token_initialization:
+            try:
+                self._endpoint.request(self.M_INITIALIZE_PROGRESS, {'token': token}).result(timeout=1.0)
+            except Exception:  # pylint: disable=broad-exception-caught
+                log.warning(
+                    "There was an error while trying to initialize progress reporting."
+                    "Likely progress reporting was used in a synchronous LSP handler, "
+                    "which is not supported by progress reporting yet. "
+                    "To prevent waiting for the timeout you can set "
+                    "`skip_token_initialization=True`. "
+                    "Not every editor will show progress then, but many will.",
+                    exc_info=True
+                )
 
         value = {
             "kind": "begin",
diff --git a/test/test_workspace.py b/test/test_workspace.py
index 94a9cba1..61c303b6 100644
--- a/test/test_workspace.py
+++ b/test/test_workspace.py
@@ -327,19 +327,24 @@ def test_progress_simple(workspace, consumer):
 
 
 @pytest.mark.parametrize("exc", [Exception("something"), TimeoutError()])
-def test_progress_initialization_fails(workspace, consumer, endpoint, exc):
+def test_progress_initialization_fails_but_is_skipped(workspace, consumer, endpoint, exc):
     def failing_token_initialization(self, *_args, **_kwargs):
         raise exc
     endpoint._dispatcher.m_window__work_done_progress__create = failing_token_initialization
 
     workspace._config.capabilities['window'] = {"workDoneProgress": True}
 
-    with workspace.report_progress("some_title"):
+    with workspace.report_progress("some_title", skip_token_initialization=True):
         pass
 
     # we only see the failing token initialization call, no other calls
-    init_call, = consumer.call_args_list
-    assert init_call[0][0]['method'] == 'window/workDoneProgress/create'
+    progress_calls = consumer.call_args_list
+    assert all(call[0][0]["method"] == "$/progress" for call in progress_calls)
+    assert len({call[0][0]["params"]["token"] for call in progress_calls}) == 1
+    assert [call[0][0]["params"]["value"] for call in progress_calls] == [
+        {"kind": "begin", "title": "some_title"},
+        {"kind": "end"},
+    ]
 
 
 def test_progress_with_percent(workspace, consumer):