http://bugs.winehq.org/show_bug.cgi?id=30765
--- Comment #19 from Robert Schwabe wayne@ioop.de 2013-06-28 10:42:58 CDT --- Created attachment 45025 --> http://bugs.winehq.org/attachment.cgi?id=45025 WINEDEBUG="+wininet,+winhttp,+rpc,+seh,+tid"
Switched to standard authentication in the http proxy settings and tried again.
Outlook tries to connect for apprx. 5 minutes and then stops with the couldnt connect message from comment #0.