Outlook 2007 collecting POP3 to Exchange 2003 mailbox

[BrantB]

Hello,

I'm wondering if anyone has experience with this, and can therefore tell me whether or not it should work properly.

We are migrating from a very old NT4/Exchange 5.0 system (back end) with Outlook XP (aka 2002) clients running on Win2000 Pro, to an SBS2003 system with Outlook 2007 clients running on WinXP Pro. In the old system, we have the Outlook clients set to collect from our external POP mailboxes, and all of those collected emails are stored (or "delivered", if you like) in the Exchange mailboxes. This is a one-to-one relationship (i.e. one user has one Outlook profile, configured with one POP3 account and one Exchange account/mailbox, where the latter is designated as the delivery destination). It has worked well.

However, in our testing of Outlook 2007 and Exchange 2003 so far, we seem to be experiencing some outbound email flow problems when we try to set up the same type of thing. From what I've researched, it may have to do with Outlook wanting to select a different account based on the specific scenario of each message. For instance, assuming that the Exchange account is set up as "default" in the Outlook profile, then new message will be delivered using the Exchange account. However, for email coming from the external (i.e. POP) mailbox, it looks like Outlook will try to process replies to those messages by sending mail using the POP portion of the profile. Is that right?

If that is the case, is there any way to control this behaviour so that all outbound email is processed through the Exchange account (regardless of new or reply, or whether its origins are internal or external)? Or, are we just out of luck - i.e. no way to override/control which account Outlook uses to process a given message? (Oh, BTW, we would like this to be transparent to the users ... so, telling the users to manually select the Exchange account all the time, on each message, is not really what we're looking for here [smile].)

Any words of wisdom would be greatly appreciated.

Cheers!

Brant

PS - Soon, you'll see another/separate posting about the POP3 Connector for Exchange in SBS 2003 (but I'll put that one in the Exchange forum). On the one hand, it is somewhat related to this topic - but, only in so much as it may be considered an alternative to collecting the POP mail through Outlook. However, I have some concerns about the POP3 Connector, and I didn't want to make this topic too broad; I much prefer to see forums were the topics are focused and separated. I hope that is okay.

[Roady [MVP]]

Yes, instead of using the external SMTP server configuration for your POP3
account, use the configuration of the internal Exchange server.

PS: why not completely switch to having Exchange collect and send all mail?

--
Robert Sparnaaij [MVP-Outlook]
Coauthor, Configuring Microsoft Outlook 2003
http://www.howto-outlook.com/
Outlook FAQ, HowTo, Downloads, Add-Ins and more

http://www.msoutlook.info/
Real World Questions, Real World Answers

-----

"BrantB" <BrantB.415gzy@invalid> wrote in message
news:BrantB.415gzy@invalid...
>
> Hello,
>
> I'm wondering if anyone has experience with this, and can therefore
> tell me whether or not it should work properly.
>
> We are migrating from a -very- old NT4/Exchange 5.0 system (back end)
> with Outlook XP (aka 2002) clients running on Win2000 Pro, to an SBS2003
> system with Outlook 2007 clients running on WinXP Pro. In the old
> system, we have the Outlook clients set to collect from our external POP
> mailboxes, and all of those collected emails are stored (or "delivered",
> if you like) in the Exchange mailboxes. This is a one-to-one
> relationship (i.e. one user has one Outlook profile, configured with one
> POP3 account and one Exchange account/mailbox, where the latter is
> designated as the delivery destination). It has worked well.
>
> However, in our testing of Outlook 2007 and Exchange 2003 so far, we
> seem to be experiencing some outbound email flow problems when we try to
> set up the same type of thing. From what I've researched, it may have
> to do with Outlook wanting to select a different account based on the
> specific scenario of each message. For instance, assuming that the
> Exchange account is set up as "default" in the Outlook profile, then
> *new* message will be delivered using the Exchange account. However,
> for email coming from the external (i.e. POP) mailbox, it looks like
> Outlook will try to process *replies* to those messages by sending mail
> using the POP portion of the profile. Is that right?
>
> If that is the case, is there any way to control this behaviour so that
> *-all-* outbound email is processed through the Exchange account
> (regardless of new or reply, or whether its origins are internal or
> external)? Or, are we just out of luck - i.e. no way to
> override/control which account Outlook uses to process a given message?
> (Oh, BTW, we would like this to be transparent to the users ... so,
> telling the users to manually select the Exchange account all the time,
> on each message, is not really what we're looking for here [smile].)
>
> Any words of wisdom would be greatly appreciated.
>
> Cheers!
>
> Brant
>
> PS - Soon, you'll see another/separate posting about the POP3 Connector
> for Exchange in SBS 2003 (but I'll put that one in the Exchange forum).
> On the one hand, it is somewhat related to this topic - but, only in so
> much as it may be considered an alternative to collecting the POP mail
> through Outlook. However, I have some concerns about the POP3
> Connector, and I didn't want to make this topic too broad; I much prefer
> to see forums were the topics are focused and separated. I hope that is
> okay.
>
>
> --
> BrantB
> http://forums.slipstick.com
>

[BrantB]

Hi Robert,

Thanks for such a quick response!

I can understand your curiosity [smile]. Normally, where Exchange is involved, I would indeed set up the server with a full 2-way SMTP connection. But, there are several contributing factors to not going that way (this time).

In this particular case, the installation has limited (practical) options for high speed Internet connections; essentially, all that is available is a "run of the mill" DSL connection. Again, that in itself nomrally wouldn't be such an issue - but the users in this installation (sometimes) deal with very tight deadlines, and at the same time, they have to deal with large-ish attachments. So, they sometimes need to be very ... er, uh ... "progressive" about the management of their bandwidth. As such, they need to have ad-hoc control over when email flows, in either/both directions ... and a full-time 2-way SMTP connection wouldn't allow that (or at least, not nearly as easily/simply as it can be controlled using Outlook - i.e. by either not running Outlook, or selecting an "off-line" [aka local mailbox only] profile).

You may also find some more insight about this situation in the other thread that I posted, regarding SBS's POP3 Connector for Exchange ...

http://forums.slipstick.com/showthread.php?t=27926

In addition to the somewhat unique bandwidth considerations, one of the users is quite nomadic and needs to be able to access email remotely via a WebMail interface. I realize that Exchange comes with OWA ... but that would require us to open up port 80 etc. on our firewall and forward that traffic to the server. Once "exposed" like that, maintaining/hardening the server becomes much more critical (i.e. more critical than it is right now, sitting behind a firewall that has no open ports; although, granted, server maintenance is still and important task [smile]). By leaving the email configured with external POP accounts, the responsibility for hardening etc. remains with our carefully-selected ISP ... who is much better equipped to deal with that type of burden [smile].

Well, there you have a couple of the bigger considerations (and most easily explained); there are a handful of factors overall though.

So, on to your suggestion ...

If I understand correctly, you mean that for the Outbound server setting in the POP portion of the Outlook profile, I would simply put in the server name of our (internal) SBS server, instead of the usual "smtp.ourISP.com"? As I was driving home tonight, I started to wonder about something like that ... but then I thought, "naw, that's too simple - there's probably some catch to that" [shrug/smile]. Maybe not(?) [big smile]

If that's all there is to it, that will be great!!!

Brant

[Diane Poremsky [MVP]]

The only way to control it in this scenario is by setting the POP accounts
SMTP server to use the Exchange as the SMTP (mail.domain.com). Using a POP
Connector to collect the mail outside of outlook would allow all mail to be
sent through Exchange.

http://www.slipstick.com/exs/popconnect.asp has a list of connectors, many
of which are better than the ones built into SBS.

--
Diane Poremsky [MVP - Outlook]
Outlook Tips: http://www.outlook-tips.net/
Outlook & Exchange Solutions Center: http://www.slipstick.com/

Outlook Tips by email:
mailto:dailytips-subscribe-request@lists.outlooktips.net

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mailto:EMO-NEWSLETTER-SUBSCRIBE-REQUEST@PEACH.EASE.LSOFT.COM



"BrantB" <BrantB.415gzy@invalid> wrote in message
news:BrantB.415gzy@invalid...
>
> Hello,
>
> I'm wondering if anyone has experience with this, and can therefore
> tell me whether or not it should work properly.
>
> We are migrating from a -very- old NT4/Exchange 5.0 system (back end)
> with Outlook XP (aka 2002) clients running on Win2000 Pro, to an SBS2003
> system with Outlook 2007 clients running on WinXP Pro. In the old
> system, we have the Outlook clients set to collect from our external POP
> mailboxes, and all of those collected emails are stored (or "delivered",
> if you like) in the Exchange mailboxes. This is a one-to-one
> relationship (i.e. one user has one Outlook profile, configured with one
> POP3 account and one Exchange account/mailbox, where the latter is
> designated as the delivery destination). It has worked well.
>
> However, in our testing of Outlook 2007 and Exchange 2003 so far, we
> seem to be experiencing some outbound email flow problems when we try to
> set up the same type of thing. From what I've researched, it may have
> to do with Outlook wanting to select a different account based on the
> specific scenario of each message. For instance, assuming that the
> Exchange account is set up as "default" in the Outlook profile, then
> *new* message will be delivered using the Exchange account. However,
> for email coming from the external (i.e. POP) mailbox, it looks like
> Outlook will try to process *replies* to those messages by sending mail
> using the POP portion of the profile. Is that right?
>
> If that is the case, is there any way to control this behaviour so that
> *-all-* outbound email is processed through the Exchange account
> (regardless of new or reply, or whether its origins are internal or
> external)? Or, are we just out of luck - i.e. no way to
> override/control which account Outlook uses to process a given message?
> (Oh, BTW, we would like this to be transparent to the users ... so,
> telling the users to manually select the Exchange account all the time,
> on each message, is not really what we're looking for here [smile].)
>
> Any words of wisdom would be greatly appreciated.
>
> Cheers!
>
> Brant
>
> PS - Soon, you'll see another/separate posting about the POP3 Connector
> for Exchange in SBS 2003 (but I'll put that one in the Exchange forum).
> On the one hand, it is somewhat related to this topic - but, only in so
> much as it may be considered an alternative to collecting the POP mail
> through Outlook. However, I have some concerns about the POP3
> Connector, and I didn't want to make this topic too broad; I much prefer
> to see forums were the topics are focused and separated. I hope that is
> okay.
>
>
> --
> BrantB
> http://forums.slipstick.com
>