Hi,
Which version of Outlook are you using? Please verify if Outlook is installed as 32bit or 64bit version.
Basically, 32-bit connector works with Microsoft Office Outlook 2003, Microsoft Office Outlook 2007 and Microsoft Office Outlook 2010 (32-bit). 64-bit connector works with Microsoft Office Outlook 2010 64-bit. Please make sure you have installed the correct version of Hotmail Connector.
In addition, please also make sure you have installed the latest version of connector. You can download the correct version here:
Outlook Hotmail Connector 32-bit
Outlook Hotmail Connector 64-bit
Regards,
Steve Fan
TechNet Community Support