How do I know Outlook Anywhere is working?
Simple… when no one is complaining! Seriously though, it is preferable is to run diagnostics on Outlook Anywhere before subjecting it to thousands of users. The one tool that works pretty well in most cases is rpcping. Yes, it has a lot of parameters and is confusing, but it does provide pretty good diagnostic information and as long as you have the KB open, you can figure out where problems lie. Start by pinging just the RPCProxy by using the -E option. Once that works, move onto testing the mailbox server endpoints by removing the -E and adding -e 6001 instead. Similarly for 6002, 6004.
A typical command line would be something like this. Refer to http://support.microsoft.com/kb/831051 for usage details
rpcping -t ncacn_http -o RpcProxy=cas1.contoso.com -P “user,domain,password” -H 1 -F 3 -a connect -u 9 -v 3 -s mailbox.contoso.com -I ” user,domain,password ” -e 6004