Outlook / Exchange Bouncing Back Some Email Erroneously

[Ren Giesbrecht]

Hi All,

I have setup SBS 2003 for a client of mine and they are using Exchange.
This is the setup.
1. They have a hosted domain website (We don't want to host their site
locally) www.theirdomain.com and another ISP company for their DSL connection
2. They have SBS 2003 server locally with a local FQDN as
headoffice.theirdomain.com running Exchange
3. Each user has a pop3 account with the hosting company set as their
default account in Outlook and an Exchange account for their mailbox access
where everthing is stored and calendars are shared. (At this point I think
it is best if their Internet email stays with the hosting company for 24/7
support)

The Issue:
Every so often when they send emails to legitimate addresses they get the
following message some time later.

From: Administrator
Sent: Friday, September 16, 2005 2:42 AM
To: Dale
Subject: Delivery Status Notification (Delay)

This is an automatically generated Delivery Status Notification.

THIS IS A WARNING MESSAGE ONLY.

YOU DO NOT NEED TO RESEND YOUR MESSAGE.

Delivery to the following recipients has been delayed.

(e-mail address removed)

This is an Exhange message and yet by default their Outlook is set to send
messages by the SMTP server of the ISP. It works most of the time but then
these messages come back even though they are going to legitimate email
addresses.

Any thoughts would be greatly appreciated.

 

[Daniel Jaburg]

The issue might be how the receiving ISP is filtering their incoming mail to
thwart spam. My guess would be they are using REVERSE DNS as a method for
verifying that the correct server is sending e-mail for the domain. To make
it easier to explain, if you do a whois domainname.com (replace domainname
with actual name), it should indicate what the IP address for the domain's
MX record. If your server's IP address is different, then it most likely
won't allow the mail through. A way to test that is to send an e-mail
through your we host (assuming they host your mail also) and see if it goes
through. My guess also is that you only get this problem on certain
recipients, and that would be any host that's using reverse DNS to verify
where it came from.

 

[Brian Tillman]

I have setup SBS 2003 for a client of mine and they are using
Exchange.
This is the setup.
1. They have a hosted domain website (We don't want to host their site
locally) www.theirdomain.com and another ISP company for their DSL
connection
2. They have SBS 2003 server locally with a local FQDN as
headoffice.theirdomain.com running Exchange
3. Each user has a pop3 account with the hosting company set as their
default account in Outlook and an Exchange account for their mailbox
access where everthing is stored and calendars are shared. (At this
point I think it is best if their Internet email stays with the
hosting company for 24/7 support)

Exchange can be configured to use the ISP as its mail router. Then all
company mail could go through Exchange and everyone would need only one
account.

The Issue:
Every so often when they send emails to legitimate addresses they get
the following message some time later.

From: Administrator
Sent: Friday, September 16, 2005 2:42 AM
To: Dale
Subject: Delivery Status Notification (Delay)

This is an automatically generated Delivery Status Notification.

THIS IS A WARNING MESSAGE ONLY.

YOU DO NOT NEED TO RESEND YOUR MESSAGE.

Delivery to the following recipients has been delayed.

What version of Outlook are they using? Outlook 2003 has an issue whereby
if it can't send a message via a specified account, it will use another
account without telling you. If for some reason a message can't be
delivered via the POP/SMTP account, it will attempt to send using the
Exchange account.

 

[Ren Giesbrecht]

Thanks Brian,

They are using Outlook 2003 so can we do either of the following.

1. I have tried setting up Exchange on my own server with the smart hosts
settings and that seemed to work (I assume that is what you are driving at),
however I don't want their outgoing email to be from
headoffice.theirdomain.com but rather from theirdomain.com (i.e. so when
someone replies it will go to their web hosting company mailbox and not
attempt to go to the local exchange server) . Is this doable? If so I would
be thrilled.

2. If the above is not an option then can we prevent Outlook from trying to
send from the exchange account as I am sure that must be what's happening.
And then let the ISPs server handle the initial error that in fact caused
Outlook to try switching to the Exchange server to attempt the send.

Thanks again for your help.

 

[Brian Tillman]

1. I have tried setting up Exchange on my own server with the smart
hosts settings and that seemed to work (I assume that is what you are
driving at), however I don't want their outgoing email to be from
headoffice.theirdomain.com but rather from theirdomain.com (i.e. so
when someone replies it will go to their web hosting company mailbox
and not attempt to go to the local exchange server) . Is this doable?
If so I would be thrilled.

It must be, because my company does it. However, I'm not an Exchange admin
and your question is best asked in m.p.exchange.admin

 

[Noel All]

As long as your not worried about the sending and reply addresses being from
theirdomain.com then you can create another email address recipient policy
in Exchange System manager, create the policy and set it as primary and then
every mail sent, replied and forwarded will be from that address that you
set up, also you may want to let the policy update all the user attributes
with this new policy so that you wont have to do it manually.