Mail could not be sent

[ynohtnA]

Version: 2008
Operating System: Mac OS X 10.5 (Leopard)
Processor: Intel
Email Client: Exchange

I have a problem when trying to send mail with attachments above around 300KB through my work Exchange server with Entourage 2008. When I try to do so I get the following error message:

Error
Connection to the server failed or was dropped. Mail could not be sent.
Error: -3253

This is specifically a problem with Entourage 2008. If I use Outlook via Parallels on the same machine I have no problems sending attachments of any size. I also do not have this problem if I use Entourage from Mac Office 2004.

I have found that this problem does not occur if I attempt to send the mail out of hours, i.e. in the evening or at weekends presumably when the load on the exchange server is much lower. I'm assuming this is a simple timeout problem but there is no option in Entourage that I can see to increase the timeout to rectify it.

I have the latest updates to both Leopard and Office 2008 installed. A lot of my work entails sending out large attachments so this is a major problem for me.

Anthony

 

[William Smith [MVP]]

I have a problem when trying to send mail with attachments above
around 300KB through my work Exchange server with Entourage 2008.
When I try to do so I get the following error message:

Error Connection to the server failed or was dropped. Mail could not
be sent. Error: -3253

This is specifically a problem with Entourage 2008. If I use Outlook
via Parallels on the same machine I have no problems sending
attachments of any size. I also do not have this problem if I use
Entourage from Mac Office 2004.

I have found that this problem does not occur if I attempt to send
the mail out of hours, i.e. in the evening or at weekends presumably
when the load on the exchange server is much lower. I'm assuming this
is a simple timeout problem but there is no option in Entourage that
I can see to increase the timeout to rectify it.

Hi Anthony!

Entourage has no adjustable time-out settings. When you're testing
out-of-hours are you also testing from the same place or are you moving
between work and home?

A couple of questions:

1. Are you connecting to an internal (direct) or external address (OWA)
for your Exchange Server?

2. Are you inside or outside your company network when this happens?

Have a look at my blog post for optimizing your Entourage connection to
Exchange. Adjusting how your connecting may make a difference:

"Optimize Entourage to better work with Exchange"
<http://blog.entourage.mvps.org/2008/03/optimize_entourage_to_better_work_with_exchange.html>
or <http://tinyurl.com/56ea7k>

--

bill

Entourage Help Page <http://entourage.mvps.org/>
Entourage Help Blog <http://blog.entourage.mvps.org/>
YouTalk <http://nine.pairlist.net/mailman/listinfo/youtalk>
Twitter: follow <http://twitter.com/meck>