Our Exchange Win2k/SP2 server running in native mode allows our users to use OWA really well -- most of the time. When it fails, however, the user gets either a "page not found" error or it prompts them for a user ID/password/domain. If they are prompted, they put in the proper information, but they are re-prompted over and over (and they don't get locked out). The "fix" is to restart the IIS admin service, which, in turn, restarts...
a bunch of subordinate services. Restarting the subordinate services individually does not work. Any ideas? It's regrettable that you have to fix this issue by restarting IIS. You shouldn't have to do that. Have you checked for memory leaks in inetinfo.exe? You might also try taking a network capture using Network Monitor during the time at which this problem manifests itself.
I also strongly recommend moving to the latest service packs for both Windows 2000 and Exchange. These include all necessary security updates and critical updates from Windows Update.
Dig Deeper on User Authentication for Microsoft Outlook and OWA
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