This is driving me nuts! Slightly convoluted explanation, please bear with it.

At our main site, we have an SBS server using a pop3 catchall for Exchange as we're on incredibly flakey 512k DSL and we have no smart host for SMTP (stop laughing)...

We have another site at which we still use the same domain name for email + individual pop3/smtp accounts directly from our mail service provider. Through some horrible cludge I've managed to get Exchange to send mail out to them even though it's on the same domain (that's not the problem but I'd love to know how to do it properly!).

One deputy head has just swapped sites and taken their laptop with them. I exported all their mail and removed the Exchange server settings on the laptop. I then removed the actual Outlook profile including all files etc, and started a new one from scratch. Added a pop3/smtp account by the same email address they used to use at the Exchange site, then imported all their old mail from a PST.

Here's the aaaargh bit -

When receiving any mail from main site (ie sent from users behind the Exchange server) to the independent laptop account, Outlook totally botches up replying. If you reply, it seems to pick up the Exchange address, even though it's showing an SMTP address as the To: field, then get totally stuck in the outbox. If I create a new email to someone at the main site, the majority of the time the same occurs. Sending mail to normal email addresses (ie those not on our domain name/associated with Exchange) works perfectly - but any replies to our domain just jam Outlook up completely.

If I've created a new Outlook profile, where on earth is it picking this up from? Having a deputy head who can't reply to mail from school is obviously not good!

When accepting email addresses, it seems to vary between accepting them and completing as

<email@domain.com>
(email@domain.com)
and 'email@domain.com'

I'm sure there's a clue there somewhere but I'm damned if I know what it is. Spent 3 hours fiddling Monday morning and got nowhere.

Any help much much appreciated!