so, we have a sandbox environment.
two servers, one is a terminal server the other is an exchange server. the exchange server is 2008x64, the TS is 2008R2x64
outlook 2003 on the TS, installed without error. creating a profile, pointed to the exchange server, resolves the name fine and all is well.
in outlook, i can browse the few public folders that exist, and i can receive test emails sent into exchange via smtp.
in outlook, no matter what i send a new email to, they all go into the outbox and sit there. outlook is online with exchange, since i can browse the public folders.
from the terminal server, if i manually send an email via telnet to the exchange server at port 25, it gets delivered just fine.
the exchange server and the TS are on the same switch in the same place on the same domain, and nothing else is on the domain. they're happily existing together in every other way.
i've rebooted the TS, and exchange, moved stuff out of the outbox, deleted it, resent new stuff, they all get stuck in the outbox. doesn't matter if it's to an external account or internal.
the windows firewall is completely disabled on both servers, and there's no router between them. this is straight outlook connections, not rpc or rpc-over-http or outlook-anywhere, and we're not relying on autodiscover.
when i sign into OWA and send an internal or external email, when i hit send they go to drafts (and not outbox or sent)
if i run outlook in compatibility mode for xp sp3, it can't open the information store.
if i run outlook as administrator (even though i'm logged in as domain\administrator) they get stuck in the outbox still