Exchange 2007 and 2010 include Transport Rules, which allow a certain level of 'fiddling' with a message in transit when it matches a certain set of criteria, but unfortunately editing content isn't one of the supported actions.
You can add extra content to the body text (like an email...
I fear you are stuck, Fee.
It's not like you're the only person to be confounded by this, nor the first - see this post from James O'Neill 4 years ago:
http://blogs.technet.com/b/jamesone/archive/2007/06/19/campaign-for-real-numbers-update.aspx
It could be a name-resolution issue, as the Outlook client needs to be able to name-resolve the Exchange server to be able to connect. Perhaps the name-resolution issues are IP-address related - is DHCP at work here to allocate the client's IP address? Is it changing? Are the DNS setting correct?
4 Processors and 8GB of RAM? Do you mean 4 cores? 8GB is the absolute minimum for a multi-role server, and I always shy away from only just having the minimum when specing Microsoft systems. So this sounds a little undersized - I have a PC with that spec that I use for running a few VMs on in...
Two for you:
http://msexchangegeek.com/2010/01/30/rapid-transition-guide-from-exchange-2003-to-exchange-2010/
and
http://www.simple-talk.com/books/sysadmin-books/exchange-2010---a-practical-approach/
specifially the cooexistance chapter, although the rest may be of help as well (the ebook...
You don't have to reset someone's password to be able to access their mailbox - you can use EMC (or EMS) to add your account with Full Access permission, and that means it is possible to then create a MAPI profile to the mailbox and use Outlook to connect.
Mailboxes can only have one primary (sending) address by definition. That's true of other objects in the GAL as well. So the bottom line is that if you want a user to be able to send as different addresses, you need multiple objects that that user has Send As permisson on.
The Alias is the one mandatory 'name' field that you have to specificy for a mailbox. It has to be unique, as it is used to exclusively identify that mailbox. The new mailbox wizard in SP1 of Exchange 2010 will suggest one for a new mailbox, unless you have any other dependencies on the Alis...
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