How can I configure Privoxy for use with Outlook?
Versions of Outlook prior to Office 2007, use Internet Explorer components to both render HTML, and fetch any HTTP requests that may be embedded in an HTML email. So however you have Privoxy configured to work with IE, this configuration should automatically be shared, at least with older version of Internet Explorer. Starting with Office 2007, Microsoft is instead using the MS-Word rendering engine with Outlook. It is unknown whether this can be configured to use a proxy.