The last several times I checked Windows Update, I find the same 2 updates that were there before. They always are shown to be successful update installations, but they are always listed as available updates the next time I check. The one that concerns me the most is a critical update. “Cumulative Security Update for Outlook Express 6, Service Pack 1” (KB837009). The other is a driver update for the onboard sound from the motherboard manufacturer. I use Trend-Micro PC-cillin and the OE6 SP1update is also listed as a Microsoft security vulnerability problem, so I assume it is not really installed. If I check installed updates they are listed multiple times. I would appreciate any help someone can offer. Thanks in advance.

You assume correctly, they are NOT installed. Find and remove them from Add/Remove Programs, delete your Temporary Internet Files from Internet Options and try WinUp site again where they will likely 'take' for real this time.

OR you can try to apply the off-line versions found at the Catalog site. Best results happen when off-line.
http://v4.windowsupdate.microsoft.com/catalog/

Drivers from WinUP? I've never heard anything good about doing that, best to get them from the manufacturer's site instead?

Thanks for the suggestions. When I tried to remove it in Add/Remove Program, it gave an error message that said it could not properly remove it. I emptied the IE temp folder and this time it took longer to download the update, so I was hopeful. It still did not work, so I read the info sheet with the update and it lead me to a file download. I could not install it because it says I need OE SP1 which I thought I already have. I may try reinstalling IE6/OE6 SP1 and try again or use the catalog site you mentioned. Thanks again!