Extreme problem with Outlook 2003 but not 2002 (xp) !?!

[Scott Lansbury]

Hi there,

Here's the deal.
I have a user who uses an exchange server for calendar bookings /
sharing contacts / internal emails etc (saves on internet traffic over
a small link too)

Their primary email however is external (pop)
This pretty much can't be changed, it's a long story.

Anyhow.

Under Outlook 2002, if I send an email to an INTERNAL recipient and CC
an external smtp recipient (outside the domain at say hotmail for
example) Outlook 2002 knows to send the email correctly, an internal
version via exchange to internal recipients and an external version to
the "internet" recipients. (still showing one copy only in the sent
items though)

The header on the received internal email does indeed have no internet
information and of course the smtp server at the local isp serving
this small business wouldn't recognise "(e-mail address removed)" for
example anyhow.



Now,...

If I do this via Outlook 2003, it will send a single copy of the email
directly to the smtp server of the isp, which will promptly crack the
niggles and send a bounce back message saying "who is
(e-mail address removed)?"

Hopefully you're all following me?

Note the default account in both cases is the pop / smtp account not
the exchange.

Please please don't reply with "just move the mail internal and do it
all through exchange" it just can't be done in this instance and it's
been working exceptionally well for almost a year like this until
today when Outlook 2003 was loaded on to a machine.


Has anyone else encountered this and what can I do to rectify it, it's
caused me no end of headaches today.
(other issues happening at the same time, so it's been difficult to
diagnose)

 

[Jeff Stephenson [MSFT]]

This is an unfortunate (and un-intended) side-effect of a change we made
response to user requests to have messages addressed to Exchange recipients
sent via SMTP if an Internet account was specified as the sending account.
Outlook 2003 will crack the Exchange address book entry and get the SMTP
address of an Exchange recipient when sending on an Internet account.

Normally when users are hitting the problem you're seeing, I recommend that
they set the ISP account to be the default account and set the SMTP proxy
addresses of the users in their Exchange addresse book to be the external
ISP addresses. This results in all mail going through the ISP (rather than
being delivered locally in Exchange), but at least it works. It won't, as
you've discovered, work for Exchange-side distribution lists.

One thing you might try (I don't know enough about administering Exchange
to know whether it's possible) is to remove any SMTP proxy addresses from
the Exchange distribution lists. That will make it impossible for Outlook
to get an SMTP address for the DL, so it will be forced to send it via
Exchange. Of course there will be no way for external recipients to reply
to the people on the list, because there is no valid SMTP address for it.

I'm pushing to get a hot-fix done to allow people to return to the Outlook
2002 behavior via a regkey. If you could contact Product Support to make a
similar request, that would add a bit more pressure to get it done...

 

[Jeff Stephenson [MSFT]]

This is due to a change in how Outlook's SMTP handles non-SMTP addresses.
It used to be that it would just ignore anything that wasn't explicitly
marked as SMTP. In Outlook 2003, however, it will open the address book
entry for that recipient and see if there is an SMTP address for the
recipient; if there is, it will use it.

The only way I can see around the problem you're facing is to remove the
SMTP proxy addresses from all address book entries of internal users. This
will mean that Outlook won't find an SMTP address and thus will be forced
to use the Exchange address and send via Exchange. Of course such
addresses won't be repliable by Internet recipients, but that was already
the case...

 

[Guest]

I was just starting to deploy office 2003 at a clients and ran into this
specific issue. Going to roll back to office XP until this issue is
fixed.... maybe someday...

blah MS blah...

 

[Jeff Stephenson [MSFT]]

I was just starting to deploy office 2003 at a clients and ran into this
specific issue. Going to roll back to office XP until this issue is
fixed.... maybe someday...

Don't know if anyone's still paying attention to this thread, but I talked
with some of the MVPs and Diane Poremsky suggested the following solution:

1) Set the SMTP proxy addresses of the internal Exchange users to be their
addresses at the ISP.
2) Configure the Exchange server to *send* mail only, using the ISP's
server as a smarthost.
3) Set the user's profiles to make the Exchange account the default
account, and configure the POP3 account to only receive, not send.

This does everything that I think people with this topology are trying to
accomplish:

a) Their Exchange server doesn't need to have a static IP address.
b) They don't have to open their firewall to any incoming traffic.
c) All purely internal mail never leaves the Exchange server.

Does that sound like it would work for you?