Google Answers Logo
View Question
Q: Outlook with Exchange as Mailbox Store, fetching from POP3 and sending via SMTP ( Answered 5 out of 5 stars,   0 Comments )
Subject: Outlook with Exchange as Mailbox Store, fetching from POP3 and sending via SMTP
Category: Computers > Internet
Asked by: c3chris-ga
List Price: $100.00
Posted: 15 Nov 2006 20:41 PST
Expires: 15 Dec 2006 20:41 PST
Question ID: 783139
I've got numerous SBS 2003 and Standard 2003 servers with Exchange on
them, and I'm largely using it as an archive for standard POP3
accounts and for basic Contact/Calendar sharing.  The majority of the
clients are small, and POP3 does the job.  Having them route their own
mail is an unncessesary overhead that these folks don't need.  Have a
few of them on DynDNS MailHop, but that still means opening ports,
which I'd rather not do.  Most of the power from Exchange comes from
the contact/cal sharing, and I'd rather route their mail with my *nix

Here's what I'm looking to solve:  Outlook has always nailed me
unpredictably when people are sending or responding to e-mail - It
gets routed through the Exchange server "by accident" even though
their accounts are configured with the POP3/SMTP set to default. 
Undeliverable messages get bounced back and scare the natives.

So, there might be two answers.  1)  A way to make Outlook never, ever
try to send outbound messages through Exchange, or 2) A way to make
Exchange refuse the message from the get-go, on the server side,
somehow.  The key is the user never having to get a bounceback from
Exchange for outbound mail that shouldn't have been routed through it
in the first place.

Hep me hep me.  Please let me know if I haven't been clear enough -
This is my first Answers post.

Thanks in advance.

Clarification of Question by c3chris-ga on 20 Nov 2006 22:23 PST
Must be too complex for $20.  Raised to $100.  =)
Subject: Re: Outlook with Exchange as Mailbox Store, fetching from POP3 and sending via
Answered By: hummer-ga on 25 Nov 2006 09:52 PST
Rated:5 out of 5 stars
Hi c3chris,

I'm sorry it has taken over a week for someone to respond to your
question, perhaps the reason being that you probably won't be 100%
satisfied with the solution  After researching this issue, I've
discovered that you are not alone and what you describe is a common
complaint. For possible solutions, please click on the following links
for full details.

"A number of small businesses have a problem with their topology --
they use an Exchange server that is not connected to the Internet and
a separate connection to an ISP for external mail. They use the
Exchange server for internal mail and calendaring, while all external
email is sent via a POP3 account in Outlook to the ISP. The POP3
account is configured as the default, the Exchange account is
Each version of Outlook handles this scenario a bit differently, but
when it worked, it worked fine. When it fails, as it often does, it
causes headaches all around.
In Outlook 2003 when the SMTP transport is presented with an Exchange
address it opens the address book entry for that recipient and uses
their default SMTP address. So now, in the above topology, sending a
message to mixed internal/external recipients sends it to all
recipients via the ISP. Since Exchange is not on the Internet, the
SMTP addresses for internal recipients are not deliverable and all
internal recipients bounce. If you reverse the order of the accounts,
Exchange handles all recipients but bounces all external recipients
because it doesn't have an Internet connection for SMTP."
"The simplest solution is to add the user's external SMTP address to
their Exchange account as the default SMTP. The messages will be
deliverable this way, although you may not want internal messages
going out the Internet. Not only does it increase bandwidth, sending
confidential documents to an Internet account may be a security
A better solution goes one step farther. Not only do you add each
users external SMTP address as their default SMTP, you also configure
Exchange to send mail to the Internet, either directly or by
forwarding it to your ISP or external mail server using Exchange
Server's smart host feature. (Keep in mind that if you don't have a
commercial IP address, messages sent directly from your server may be
blocked by Real time block lists.)"
"While POP3 connectors are discouraged by most Exchange
administrators, if you are going to use external mailboxes it's much
better to use a connector and collect everyone's email from a central
point on a regular schedule, passing it through virus and anti-spam
scanners before depositing it in the Exchange mailboxes, rather than
each employee collecting their own email as often as they want."

1) You could use the SBS 2003 POP3 Connector tool
2) You could use some other POP3 Connector program
3) You could simply set the Exchange account as the default in Outlook

"It is widely known that Microsoft Exchange Server 2000/2003 doesn't
support receiving mail through the POP3 protocol. However, in
practice, it has been shown that many users find the absence of this
feature inconvenient. All the existing solutions entice users to use a
utility agent receiving mail through the POP3 protocol and delivering
it to the Exchange Server through the SMTP protocol. This is a
versatile solution equally usable for most SMTP-servers. However,
there are a number of negatives with this method... "

1) SBS POP3 Connector tool

How to?Get Connected With POP3
Already installed by default, you will access and configure the POP3
Connector using the following steps...

Install this patch before enabling the connector.

2) Other Connectors

Connecting Microsoft Exchange Server to a POP3 Account
All of the commercial POP3 connectors should be able to deliver mail
to any SMTP address, including mail-enabled Public Folders.

3) Exchange as Default

I hate Microsoft Exchange. Let me explain why.
"So far, I?ve found that Outlook - when configured to use Exchange and
a POP3 account - doesn?t like to send email through the default SMTP
server, say '' Instead, it just seems to ?forget?
that it?s supposed to use that server, and instead says 'oh, I?m
configured for Exchange - obviously they must?ve wanted to send it
through Exchange. I?ll just do that for you!'"
And then the Exchange server says 'wait a minute there, sparky. I?m
not relaying anything for you (even though I?ve been configured for
open relay and you?re properly authenticated). BOUNCE!'"
"I?ve never found a ?solution? for the problem; only a ?workaround.?
And like I said, the workaround is to make the Exchange account the
?default? account in Outlook, thus causing all outgoing mail to be
sent through Exchange (which will then forward it to your ?real? SMTP
server). Otherwise, it just doesn?t work."
"In the end, I had to switch everyone?s email settings to use the
Exchange server as the default for outgoing mail"

I hope this helps. If you have any questions, please post a
clarification request and wait for me to respond before closing/rating
my answer.

Thank you,

Google Search Terms Used: exchange server outlook pop3 connector smtp bounce
c3chris-ga rated this answer:5 out of 5 stars
Couldn't have said it better.  Thank you.

There are no comments at this time.

Important Disclaimer: Answers and comments provided on Google Answers are general information, and are not intended to substitute for informed professional medical, psychiatric, psychological, tax, legal, investment, accounting, or other professional advice. Google does not endorse, and expressly disclaims liability for any product, manufacturer, distributor, service or service provider mentioned or any opinion expressed in answers or comments. Please read carefully the Google Answers Terms of Service.

If you feel that you have found inappropriate content, please let us know by emailing us at with the question ID listed above. Thank you.
Search Google Answers for
Google Answers  

Google Home - Answers FAQ - Terms of Service - Privacy Policy