Problems sending to external POP3 from Exchange server

[Sheldon]

I am having problems sending email from an Exchange server
to an external POP3 email account. In some instances, both
the Exchange and POP3 accounts have the same email
addresses. IN other cases, I am sending to an external
email that does not exist on the Exchange server. Even
though I have the POP3 account set as the default,
external emails are still trying to send through the
Exchange server and are getting rejected:

The e-mail account does not exist at the organization this
message was sent to. Check the e-mail address, or contact
the recipient directly to find out the correct address.
<XXXXX.xxxxx.xxxxx(exchange server address)
#5.1.1>

Is there any way to configure either Outlook or the
exchange server to send this email correctly?

Thanks,

 

[Sheldon]

I have just completed a rollout of Outlook 2002. None of
the users having this problem experienced it in Outlook
2000. However, since "upgrading" to Outlook 2002 the
problem started. The weird part of the problem is that it
does not occur for all users, it seems to be fairly random
for the users it affects. An additional note, I have
compared Outlook setting on one the works and one that
fails, and the settings appear to be indentical.

RE:Selecting the external account from drop down
list.....This does work for users having this problem, but
my confusion is....why is it happening to only some users
and not all???

Thanks,
Sheldon

 

[Jeff Stephenson [MSFT]]

Is the external mail that's being sent through the Exchange server perhaps a
reply to mail that has been *received* by the Exchange server? Outlook will
default the account for a reply to the account on which the original message
was received, so if the message came in through the Exchange server, the
Exchange server will be the first account tried for a reply.

 

[Sheldon]

Yes, the problem is usually with email the is being
forwarded from an Internal Exchange account to and
External POP3 account. It also occurs occasionally when
replying to External POP3 Email even if the default
sending account is the external account

 

[Sheldon]

This does sound vey much like the problem I am having.

One difference is that our internal Exchange emails addresses are the
same as our External POP3 addresses. I think this may be part of the
problem. Example:

Exchange email address: (e-mail address removed)
External POP3 email: (e-mail address removed)

Could this problem be resolved by making the internal and external
accounts different addresses? Would this cause additional problems?

WE are considering changing our email setup to resolve this issue,
but we are still investigating. You stated that Outlook 2003 would
resolve this issue. Which solution would be better to resolve this
problem.....OWA or Outlook 2003?

Thanks

Outlook will always try sending a forwarded message on the default account
first, unless a different account is selected. On a reply, Outlook will
always first try to send the message on the account through which the
original message was received, again, unless a different account is
selected. However, if the first account Outlook tries to send on cannot
handle all the recipients, it will then try the next account in the account
order, and continue through all the accounts until either the message has
been sent to all the recipients or it runs out of accounts to try.

One thing that does happen in Outlook 2002 when Exchange is involved is that
all recipient's addresses that resolve to an Exchange address (i.e. any
address in the GAL) will not be able to be delivered via an Internet
account - the address is an Exchange address, not an Internet address. So
even if you explicitly say to send a message via your external POP3 account,
if some of the recipients are in your GAL the message will be delivered to
them via Exchange. This will happen even if you enter the address as an
Internet address - Outlook will resolve that address against the GAL and
replace it with an Exchange address. This will *not* happen in Outlook
2003 - in that case, if Outlook is trying to send to an Internet account, it
will query the address book and attempt to find an SMTP address that it can
use for the recipient.

Does what you're seeing match the behavior described above?

--
Jeff Stephenson
Outlook Development
This posting is provided "AS IS" with no warranties, and confers no rights

Yes, the problem is usually with email the is being
forwarded from an Internal Exchange account to and
External POP3 account. It also occurs occasionally when
replying to External POP3 Email even if the default
sending account is the external account

Outlook
2000, you probablymail.
Outlook 2002message
is to be senton
the message.and
confers no rights

 

[Jeff Stephenson [MSFT]]

The fact that both your internal and external email addresses are the same
is what's causing this problem - if you type in the SMTP address for a user,
it will be resolved to an Exchange address that only Exchange will be able
to handle. While Outlook 2003 will solve this problem by getting the SMTP
address from the address book entry for the Exchange user and then using the
account that you specified to send the mail, you're probably better off
changing your mail system - a setup in which each user's mail address is
hosted on two different servers is just asking for trouble.

You *could* use different addresses for your external and internal accounts,
but that will have its own set of problems. For example, if you send a
message to a customer and include an internal email address in the
recipients, when the customer replies the internal recipient will never get
the message because that address is not valid on the Internet. You're much
better off settling on a single mail provider - probably your Exchange
server, which would need to be connected to the Internet.

--
Jeff Stephenson
Outlook Development
This posting is provided "AS IS" with no warranties, and confers no rights

This does sound vey much like the problem I am having.

One difference is that our internal Exchange emails addresses are the
same as our External POP3 addresses. I think this may be part of the
problem. Example:

Exchange email address: (e-mail address removed)
External POP3 email: (e-mail address removed)

Could this problem be resolved by making the internal and external
accounts different addresses? Would this cause additional problems?

WE are considering changing our email setup to resolve this issue,
but we are still investigating. You stated that Outlook 2003 would
resolve this issue. Which solution would be better to resolve this
problem.....OWA or Outlook 2003?

Thanks


"Jeff Stephenson [MSFT]" <[email protected]> wrote in

Outlook will always try sending a forwarded message on the default account
first, unless a different account is selected. On a reply, Outlook will
always first try to send the message on the account through which the
original message was received, again, unless a different account is
selected. However, if the first account Outlook tries to send on cannot
handle all the recipients, it will then try the next account in the account
order, and continue through all the accounts until either the message has
been sent to all the recipients or it runs out of accounts to try.

One thing that does happen in Outlook 2002 when Exchange is involved is that
all recipient's addresses that resolve to an Exchange address (i.e. any
address in the GAL) will not be able to be delivered via an Internet
account - the address is an Exchange address, not an Internet address. So
even if you explicitly say to send a message via your external POP3 account,
if some of the recipients are in your GAL the message will be delivered to
them via Exchange. This will happen even if you enter the address as an
Internet address - Outlook will resolve that address against the GAL and
replace it with an Exchange address. This will *not* happen in Outlook
2003 - in that case, if Outlook is trying to send to an Internet account, it
will query the address book and attempt to find an SMTP address that it can
use for the recipient.

Does what you're seeing match the behavior described above?

--
Jeff Stephenson
Outlook Development
This posting is provided "AS IS" with no warranties, and confers no rights



Outlook
2000, you probably
mail.
Outlook 2002
message
is to be sent
on
the message.
and
confers no rights