I took a closer look at the IIS logs for the application I'm trying to get to and found some interesting things. Take note of the client IPs in the failure case. I added some comments to each request at the end of the line in bold/italics. Again, I removed IPs and replaced as follows:
<ServerIP /> = application IP
<ClientIP-A /> = client IP when MS Word makes the [initial] request
<ClientIP-B /> = client IP when IE makes the request
#Fields: date time s-ip cs-method cs-uri-stem cs-uri-query s-port cs-username c-ip cs(User-Agent) sc-status sc-substatus sc-win32-status time-taken
Starting from MS Word (failure):
2010-02-03 13:46:23 <ServerIP /> GET / - 443 - <ClientIP-A /> 302 0 0 1937 MSWord makes request and the claims aware agent detects no token so redirects to FS resource server URL, but first establishes a context via a cookie
2010-02-03 13:46:29 <ServerIP /> POST / - 443 - <ClientIP-B /> 302 0 0 125 IE POSTS back a token generated from the resource server. Cliams aware agent cannot extract the context from the cookie and redirects to an error page within the application.
2010-02-03 13:46:29 <ServerIP /> GET /Error.aspx aspxerrorpath=/ 443 - <ClientIP-B /> 302 0 0 125 IE attempts a GET of the error page, but it also requrires authentication and we redirect back to the FS resource server, which ultimately stops this process and displays an error page that does not require authentication
Starting from IE (success):
2010-02-03 13:47:51 <ServerIP /> GET / - 443 - <ClientIP-B /> 302 0 0 125 IE makes a request and the claims aware agent detects no token so redirects to FS resource server URL, but first establishes a context via a cookie
2010-02-03 13:47:55 <ServerIP /> POST / - 443 - <ClientIP-B /> 302 0 0 1156 IE POSTS back a token generated from the resource server. Claims aware agent extracts the context correctly from the cookie and redirects the user to the appropriate URL they originally requested.
Also, the user agent for ALL requests appear to be identical and all start with:
Mozilla/4.0+(compatible;+MSIE+7.0;
So, my question is, where does the cookie go that gets generated by the claims aware agent in step 1 of the failure case? Which process owns the cookie (word or IE)? Seems like this is a GOOD thing that the problem is occuring from a security perspective; however, it would be nice to know why the source IP from the MS Word request is different. Note that my desktop is behind firewalls and proxies and that <ClientIP-B> is the proxy server configured in IE.