Send mail with exchange server disappears,outlook webaccess get delivered

[ParadoX_Design]

Version: 2004
Operating System: Mac OS X 10.4 (Tiger)
Processor: Power PC
Email Client: Exchange

Hi there fellow Entourage users..
Been an Entourage user from day one but have an issue at one of my customers that I just can't tackle..

User, on an iMac, (PPC) running Tiger using Entourage 2004 with al the latest patches.

When she sends mail using Entourage (Via an Exchange Webdav connection through her server using an internet connection (ADSL) the mails will not reach the recipient. They get blocked, causing the recipient server to send an NDR or just disappear without a trace!

When I trace the message in Exchange, the server states that the mail is routed to the internet and send. (!)

When I send a mail to the same recipient using Outlook Webaccess (with the same useraccount), the message is delivered! It almost looks as Entourage adds some stuff along the way causing spam software to go bezerk and just drop the mail or reject it.

I've been around in "mail-county" but this leaves me standing on the electronic highway with my pants down..

I hope someone can shine some light on this problem..

Best regards and my gratitude if you could help me with this!

Pascal
ParadoX Design

 

[William Smith [MVP]]

User, on an iMac, (PPC) running Tiger using Entourage 2004 with al
the latest patches.

When she sends mail using Entourage (Via an Exchange Webdav
connection through her server using an internet connection (ADSL) the
mails will not reach the recipient. They get blocked, causing the
recipient server to send an NDR or just disappear without a trace!

The "recipient server"? Do you mean your own Exchange server or the
recipient's server?

What does the NDR say is the reason the message was not received?

When I trace the message in Exchange, the server states that the mail
is routed to the internet and send. (!)

Are you saying you have access to the Exchange Server's logs and can see
no errors?

When I send a mail to the same recipient using Outlook Webaccess
(with the same useraccount), the message is delivered! It almost
looks as Entourage adds some stuff along the way causing spam
software to go bezerk and just drop the mail or reject it.

So, if the message is getting delivered to the recipient but you're
receiving an error from your Exchange Server then the problem is with
your Exchange Server and not Entourage.

I would suggest also posting your question in the
microsoft.public.exchange.admin newsgroup to see if anyone there has
seen this behavior before.

--

bill

Entourage Help Page <http://entourage.mvps.org/>
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[ParadoX_Design]

Hi Bill, thanks for your reply..!

I think, in retrospect, that the ndr's are coming from the remote server. One time I got a "Content Rejected" error message.. Sometimes the messages get routed (checked through message tracking) and are not delivered to the recipient. My guess is that spam engines block and discard the message.
The weird thing is that sending with entourage to recipient A results in a loss of the message for no appearant reason, but when I send the message via outlook webmail (on the same exchange server) it gets delivered..?

The one that said "content blocked" worries me the most, at first I thought that it could have something to do with the signature send with the file (containing a gif file) but removing that didn't do the trick either.

The problem has been going on for a while now and just recently I figured out that it's got something to do with Entourage..