diff --git a/telegram/utils/request.py b/telegram/utils/request.py
index db948fb3049..ca3a7731eaf 100644
--- a/telegram/utils/request.py
+++ b/telegram/utils/request.py
@@ -323,7 +323,8 @@ def post(self, url, data, timeout=None):
         else:
             result = self._request_wrapper('POST', url,
                                            body=json.dumps(data).encode('utf-8'),
-                                           headers={'Content-Type': 'application/json'})
+                                           headers={'Content-Type': 'application/json'},
+                                           **urlopen_kwargs)
 
         return self._parse(result)
 
diff --git a/tests/test_bot.py b/tests/test_bot.py
index fe3b38736c7..a84d52abfaf 100644
--- a/tests/test_bot.py
+++ b/tests/test_bot.py
@@ -618,16 +618,27 @@ def test_error_pin_unpin_message(self, bot, message):
     # test_sticker module.
 
     def test_timeout_propagation(self, monkeypatch, bot, chat_id):
+
+        from telegram.vendor.ptb_urllib3.urllib3.util.timeout import Timeout
+
         class OkException(Exception):
             pass
 
-        timeout = 500
+        TIMEOUT = 500
 
-        def post(*args, **kwargs):
-            if kwargs.get('timeout') == 500:
+        def request_wrapper(*args, **kwargs):
+            obj = kwargs.get('timeout')
+            if isinstance(obj, Timeout) and obj._read == TIMEOUT:
                 raise OkException
 
-        monkeypatch.setattr('telegram.utils.request.Request.post', post)
+            return b'{"ok": true, "result": []}'
+
+        monkeypatch.setattr('telegram.utils.request.Request._request_wrapper', request_wrapper)
+
+        # Test file uploading
+        with pytest.raises(OkException):
+            bot.send_photo(chat_id, open('tests/data/telegram.jpg', 'rb'), timeout=TIMEOUT)
 
+        # Test JSON submition
         with pytest.raises(OkException):
-            bot.send_photo(chat_id, open('tests/data/telegram.jpg', 'rb'), timeout=timeout)
+            bot.get_chat_administrators(chat_id, timeout=TIMEOUT)