Not sure what is going on... looking at a possible rebuild if it can't be figured out.
Windows 98SE, Internet Explorer 5.5, Outlook 2000. Have tried repeatedly to print emails (Sent Items, Inbox, Deleted Items) as well as any webpage. Nothing at all... its as if I hadn't even clicked on the printer icon or gone to File - Print or File - Print Preview. Reinstalled the printer drivers - HP LJ4100 on the network. Am able to do Windows test page, Wordpad and MS Word - those print fine. Just emails and webpages.
IE has all the critical updates.