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howto setup SMTP Connectors to single/multiple smarthosts?

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Mark Yashinsky

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Oct 4, 2005, 5:11:06 PM10/4/05
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Have multiple W2K user machine (minimum SP4) and Outlook 2003 (SP1) that
connects to a new SBS 2003 (SP1). All e-mail is via "smarthost". Attempting
to set Exchange up to initially send (SMTP) to a smarthost that requires a
different "Outbound Security" setting for each email user. Later, want to be
able to send to any smarthost based on the email that the user set up
(different smarthost/name/password). Currently have POP3 Connector bringing
in the mail from multiple smarthosts/name/password just fine.
The SMTP Virtual Server has no "Smart Host" or "Outbound Security" set up
(should send everything to the SMTP Connectors, right?). Currently have
multiple SMTP Connectors set up, one for each user's e-mail address, that has
mail forwarded to the correct smart host, the SBS server as bridgehead,
Outbound Security info correct for each users e-mail requirement AND Delivery
Restrictions set to allow only (hopefully) that user into that Connector and
reject all others. Also, have changed the Registry per KB277872, "Connector
Delivery Restrictions May Not Work Correctly".
The problem looks to be that the wrong Connector is being used to send mail,
which means that the wrong name/password is being used to AUTH LOGIN into the
smarthost and it rejects the e-mail sent with a "550 5.7.1 Authentication is
required to send mail as..." and the e-mail comes back to the user. Pushed
the logging up to maximum and cannot see the actual name/password going out
for the AUTH LOGIN command in the SMTPSVC1 log (any way of logging this?) but
the the next command MAIL TO fails with authenication. Consistent with the
results I get on a Telnet session to the smarthost.
The Connector selection process looks to be random. I can have user A able
to send, and user B fail, then wait a while and user B will work and user A
fails. Or user A can continue to work. Bouncing the SMTP and Routing engine
does not seem to have an effect on this selection process. Deleting all
Connectors but one, allows the user assigned to that Connector to send
consistantly.
Have gone through all the SBS/Exchange setup docs, searched the Microsoft
KB's and these newsgroups and not found anything definitive. Have seen this
issue posted on other forums on the Net, but no real answer was given.
Any solid ideas on how to fix this or to set this up correctly? Thanks...

Bharat Suneja

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Oct 4, 2005, 6:57:19 PM10/4/05
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Exchange Server 2003 Message Routing - scroll down and read the
load-balancing stuff.

http://www.microsoft.com/technet/prodtechnol/exchange/guides/E2k3TechRef/8d5fba50-9a24-4978-9b33-4a3a04cad9d1.mspx

Multiple Connectors with same Address Space & Cost are load-balanced if
using different Bridgeheads. If using same BH, one Connector is selected and
cached.

1) Ideally you'd want Routing Engine to look at Delivery Restrictions as
well before/when selecting the Connector. Doesn't happen.

2) When message gets to the Connector with Delivery Restrictions, and the
user does not have permissions, it is NDRed. Ideally, RE should re-route the
message if there is another Connector with same Address Space & Cost
present.

(Does this answer your question... ?)

--
Bharat Suneja
MCSE, MCT
--------------------------------


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Javier Gomez [SBS MVP]

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Oct 4, 2005, 9:10:49 PM10/4/05
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Let me see if I understand your question-> You want to use a different
username/password each time Exchange sends an email to a smarthost based on
the sender address?

AFAIK-> That is not possible to do in Exchange. On the other hand, it is
also probably unnecessary. After you authenticate with a smarthost you can
probably relay from any address.

Can you send mail at all? Also, any chance you are using Verizon as a
smarthost?

--
Javier [SBS MVP]
www.msmvps.com/javier
<< SBS ROCKS !!! >>

"Mark Yashinsky" <MarkYa...@discussions.microsoft.com> wrote in message
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Bharat Suneja

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Oct 4, 2005, 10:21:45 PM10/4/05
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It DOES NOT reroute messages - if the sender doesn't have permissions to
send out of one Connector based on Delivery Restrictions (or whatever... )
it will NDR the message rather than look for another Connectors with same
Address Space & Cost.

Not to say that it's not possible - I'm hearing it can be done, just don't
have details nailed down right now and not sure if I will soon.... It's not
something obivious that you can do from the ESM UI.


--
Bharat Suneja
MCSE, MCT
--------------------------------

"Mark Yashinsky" <MarkYa...@discussions.microsoft.com> wrote in message
news:6EBE3FB7-6305-43AB...@microsoft.com...
> Javier, yes, they ARE the main problem right now, however, getting some
> serious bandwidth from them (FIOS). Find it hard to believe that
> (supposedly) Outlook Express can be set up to handle Verizon, yet,
> Exchange
> 2003 cannot?!?!
> Bharat, the caching is probably what is happening w/ the Connectors and
> why
> one gets selected and stays selected. Your item 2, are you saying the
> R.E.
> DOES reroute to another Connector or like item 1, it should, but does not?
> Still reading and understanding the whole TechNet link you posted.
> Thanks.
>
> Bottom line, it sounds like Exchange 2003 currently cannot (ever???)
> handle
> a Verizon like smarthost, and need to send directly by getting a domain
> name,
> correct?


Gareth Winn

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Oct 5, 2005, 7:57:09 AM10/5/05
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do you have a static IP adress for your internet connection? If so then just
use DNS to route the emails as it need to. you don't need to relay messages
to send them to people across the internet. Should still be able to send
directly via Exchange even if the IP addy is dynamic.

Why don't you get your MX record for the domain pointed to your IP addy and
save all the hassle? Domain name registration and DNS management only costs
about £50 for 2 years

Gareth

Javier Gomez [SBS MVP]

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Oct 5, 2005, 12:38:08 PM10/5/05
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Yes... the problem started a couple of months ago with Verizon. They changed
the way AUTH commands work (non RFC compliant) and now they don't work with
Exchange (but Outlook and OE works).

The best bet is to use another smarthost (DynDNS.org offers one for a low
price) unless you have a static IP, in which case just use DNS instead.

--
Javier [SBS MVP]
www.msmvps.com/javier
<< SBS ROCKS !!! >>

"Mark Yashinsky" <MarkYa...@discussions.microsoft.com> wrote in message

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