diff --git a/matrix_client/api.py b/matrix_client/api.py
index cb726aca..44b9584a 100644
--- a/matrix_client/api.py
+++ b/matrix_client/api.py
@@ -16,7 +16,7 @@
 import json
 import requests
 from time import time, sleep
-from .errors import MatrixError, MatrixRequestError
+from .errors import MatrixError, MatrixRequestError, MatrixHttpLibError
 
 try:
     from urllib import quote
@@ -585,13 +585,16 @@ def _send(self, method, path, content=None, query_params={}, headers={},
 
         response = None
         while True:
-            response = requests.request(
-                method, endpoint,
-                params=query_params,
-                data=content,
-                headers=headers,
-                verify=self.validate_cert
-            )
+            try:
+                response = requests.request(
+                    method, endpoint,
+                    params=query_params,
+                    data=content,
+                    headers=headers,
+                    verify=self.validate_cert
+                )
+            except requests.exceptions.RequestException as e:
+                raise MatrixHttpLibError(e, method, endpoint)
 
             if response.status_code == 429:
                 sleep(response.json()['retry_after_ms'] / 1000)
diff --git a/matrix_client/errors.py b/matrix_client/errors.py
index 10cd039f..1662dd3d 100644
--- a/matrix_client/errors.py
+++ b/matrix_client/errors.py
@@ -5,6 +5,7 @@ class MatrixError(Exception):
 
 class MatrixUnexpectedResponse(MatrixError):
     """The home server gave an unexpected response. """
+
     def __init__(self, content=""):
         super(MatrixError, self).__init__(content)
         self.content = content
@@ -17,3 +18,13 @@ def __init__(self, code=0, content=""):
         super(MatrixRequestError, self).__init__("%d: %s" % (code, content))
         self.code = code
         self.content = content
+
+
+class MatrixHttpLibError(MatrixError):
+    """The library used for http requests raised an exception."""
+
+    def __init__(self, original_exception, method, endpoint):
+        super(MatrixHttpLibError, self).__init__(
+            "Something went wrong in {} requesting {}: {}".format(original_exception)
+        )
+        self.original_exception = original_exception