Jeremy - it sounds like you and I are having the same problem. I think that after 20 minutes ASP.NET is trying to verify the cookie, but cannot decrypt it for some reason. For me I do not have any ASP 1.1 sites on my DEV server. Also, I only have 3 test users that access the site - and the behaviour is consistent - after 20 minutes the error occurs and the users get prompted to login.
I did just notice that this behaviour in occuring only on my DEV server, but not on my PRD server. Weird!
DEV - Windows XP Pro x64 with SP2, running IIS5.1, ASP.NET 2.0, SQL 2005, everything fully patched
PRD - Windows 2003 Server 32 bit, running IIS6, ASP.NET 1.1 and 2.0, SQL 2005, everything fully patched
As you and others are experiencing the problem on Windows 2003, we can assume it's not a difference between IIS5.1 and IIS6. As I am not experiencing the problem on my PRD server, I don't think that it's because of ASP.NET 1.1.
My only lead at this point is that the idea that the perhaps the cookie encryption is different from the decryption.
Also noticed that I seem to have 2 cookies when I visit my site. One is called ITM_AUTH_COOKIE, and it's the one that I create and set the cookie timeout of 14 days on. The other is called ASP_NET.Session_ID, and I don't know how it gets created. It's timeout is set to the end of the session. Perhaps that is a clue?
Cheers,
Mike