diff --git a/grpclib/protocol.py b/grpclib/protocol.py
index 356f77f..91973f3 100644
--- a/grpclib/protocol.py
+++ b/grpclib/protocol.py
@@ -301,10 +301,12 @@ class Stream:
                 await self._connection.write_ready.wait()
 
             window = self._h2_connection.local_flow_control_window(self.id)
-            if not window:
+            if not window > 0:
                 self.__window_updated__.clear()
                 await self.__window_updated__.wait()
-                window = self._h2_connection.local_flow_control_window(self.id)
+                # during "await" above other streams were able to send data and
+                # decrease current window size, so try from the beginning
+                continue
 
             max_frame_size = self._h2_connection.max_outbound_frame_size
             f_chunk = f.read(min(window, max_frame_size, f_last - f_pos))
diff --git a/tests/test_protocol.py b/tests/test_protocol.py
index ff42631..32287eb 100644
--- a/tests/test_protocol.py
+++ b/tests/test_protocol.py
@@ -215,7 +215,7 @@ async def test_initial_window_size_update(loop):
     assert client_h2c.local_flow_control_window(client_stream.id) == 1
     await asyncio.wait([send_task], timeout=0.01)
 
-    assert send_task.done()
+    assert send_task.result() is None
 
 
 @pytest.mark.asyncio
@@ -337,3 +337,55 @@ async def test_released_stream_data_ack(loop):
     to_server_transport.process(server_proc)
     # client-side flow control window will increase to initial value eventually
     assert client_h2c.outbound_flow_control_window > 1
+
+
+@pytest.mark.asyncio
+async def test_negative_window_size(loop):
+    client_h2c, server_h2c = create_connections()
+
+    to_client_transport = TransportStub(client_h2c)
+    server_conn = Connection(server_h2c, to_client_transport, loop=loop)
+
+    to_server_transport = TransportStub(server_h2c)
+    client_conn = Connection(client_h2c, to_server_transport, loop=loop)
+
+    client_proc = EventsProcessor(DummyHandler(), client_conn)
+    client_stream = client_conn.create_stream()
+
+    await client_stream.send_request(create_headers(), _processor=client_proc)
+
+    # data should be bigger than window size
+    initial_window = server_h2c.local_settings.initial_window_size
+    data = b'0' * (initial_window + 1)
+
+    assert (client_h2c.local_flow_control_window(client_stream.id)
+            == initial_window)
+
+    # send_data should wait until settings/window updated
+    send_task = loop.create_task(client_stream.send_data(data))
+    await asyncio.wait([send_task], timeout=0.01)
+
+    assert client_h2c.local_flow_control_window(client_stream.id) == 0
+
+    # updating settings, this should decrease connection window size
+    server_h2c.update_settings({
+        SettingCodes.INITIAL_WINDOW_SIZE: initial_window - 1
+    })
+    server_conn.flush()
+    to_client_transport.process(client_proc)
+
+    # window is negative and client should wait
+    assert client_h2c.local_flow_control_window(client_stream.id) == -1
+    await asyncio.wait([send_task], timeout=0.01)
+    assert not send_task.done()
+
+    # now `send_data` should succeed
+    server_h2c.increment_flow_control_window(2, stream_id=client_stream.id)
+    # INITIAL_WINDOW_SIZE not changes connection's window size, so it should be
+    # incremented only by 1
+    server_h2c.increment_flow_control_window(1, stream_id=None)
+    server_conn.flush()
+    to_client_transport.process(client_proc)
+    assert client_h2c.local_flow_control_window(client_stream.id) == 1
+    await asyncio.wait([send_task], timeout=0.01)
+    assert send_task.result() is None