What steps will reproduce the problem? 1. >>> h = httplib2.Http() >>> h.request("https://arcgis.vdem.virginia.gov/arcgis/rest/services/&quot;) Traceback (most recent call last): File "<stdin>", line 1, in <module> File "httplib2/init.py", line 1591, in request (response, content) = self._request(conn, authority, uri, request_uri, method, body, headers, redirections, cachekey) File "httplib2/init.py", line 1333, in _request (response, content) = self._conn_request(conn, request_uri, method, body, headers) File "httplib2/init.py", line 1255, in _conn_request conn.connect() File "httplib2/init.py", line 1044, in connect raise SSLHandshakeError(e) httplib2.SSLHandshakeError: [Errno 1] _ssl.c:504: error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed

http://www.sslshopper.com/ssl-checker.html#hostname=arcgis.vdem.virginia.gov shows the certificates. It looks like cacerts is a pretty limited set.