We had the same issue migrating from GroupWise to Exchange 5.5 a few years
back.  

Outlook doesn't really cache anything in the sense that you're talking about.
It merely neglects to re-look-up the address in a reply.  Normally, this
makes sense.  If you send me a message and I reply, there's no reason to
waste the CPU cycles or the bandwidth to verify that the address still
exists.  

What we told people to do is when they get the bounce messages, do a resend,
delete all of the addresses from the From, CC, etc. fields and type them
again.  This forces a new GAL lookup and should find the up to date
addresses.  This will be a problem that will lessen as time goes on.  

> -----Original Message-----
> From: Matt Hoffman [mailto:[EMAIL PROTECTED] 
> Sent: Monday, November 24, 2003 11:56 AM
> To: Exchange Discussions
> Subject: Silly Outlook Addressing Problem
> 
> 
> OK, I'm sure this is a newbie question, but I don't even know what to
> call this problem in order to look it up:
> 
> After our upgrade to Exchange 2000 from 5.5 many of our users are
> experiencing a problem where they are getting undeliverable emails to
> other staff members.  This is definitely a problem with the X400
> addresses, since they have changed and the SMTP addresses 
> have not (and
> in fact, when looking at their "sent item" I can see the old X400
> address from the 5.5 system is still in there).
> 
> So, I surmise that the problem has to do with how Outlook holds on to
> past email addresses.  My guess is that the users are 
> responding to old
> emails that came from users back when the old system was in place and
> are therefore getting the old X400 addresses.  This is sticking in
> Outlook's "cache" (again, note that I'm not an Outlook expert) and
> causing problems when they then attempt to send to that user again.
> 
> So, two possible related solutions:
> 
> 1.  get rid of the X400 addresses if they are not necessary.  We have
> only one Exchange server and are not likely to get another.  Do we
> really need them?
> 
> 2.  Figure out how to turn off Outlook's "caching" of email addresses.
> How does one do that?  Is there a way to do it via Active Directory
> GPO's?
> 
> Thanks for any help,
> 
> Matt
> 
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