Entourage 2004 + SSL + load balancer = corrupt attachments

R

rjrbytes

We (my place of work) recently put a pair of new SMTP servers into
production with a Cisco load balancer in front to distribute
connections between the two servers. Whenever we use SSL encryption
on an SMTP connection with Entourage v.2004, any attachments we send
are corrupted. The attachments are sent fine if a non-SSL connection
is used. Has anybody run into this or have input on how to resolve
(without switching to Thunderbird or other email clients which work
fine with the same settings)?

-Robert
 
D

Diane

We (my place of work) recently put a pair of new SMTP servers into
production with a Cisco load balancer in front to distribute
connections between the two servers. Whenever we use SSL encryption
on an SMTP connection with Entourage v.2004, any attachments we send
are corrupted. The attachments are sent fine if a non-SSL connection
is used. Has anybody run into this or have input on how to resolve
(without switching to Thunderbird or other email clients which work
fine with the same settings)?
Click to expand...

The only info I could find on corrupted attachments:

Change the preferences in Entourage so that attachments are set to be
encoded "... For any computer (AppleDouble); no compression; Windows file
name extension" instead of "Windows Mime/Base 64".

User reported this tip: Do you have LittleSnitch installed? If so, update to
the latest version. It specifically had problems with corrupting attachments
in Entourage. The latest version fixes that.

Read this User tip for some possible clues as to what to look for in your
setup.

<http://www.entourage.mvps.org/troubleshoot/user_exp.html#user5>
 
R

rjrbytes

The only info I could find on corrupted attachments:

Change the preferences in Entourage so that attachments are set to be
encoded "... For any computer (AppleDouble); no compression; Windows file
name extension" instead of "Windows Mime/Base 64".

User reported this tip: Do you have LittleSnitch installed? If so, update to
the latest version. It specifically had problems with corrupting attachments
in Entourage. The latest version fixes that.

Read this User tip for some possible clues as to what to look for in your
setup.

<http://www.entourage.mvps.org/troubleshoot/user_exp.html#user5>
Click to expand...

Unfortunately those attachment settings were what I had already.
LittleSnitch is not installed. We (the IT department I work in) have
run into this problem on a variety of Mac workstations and the
corruption only shows up when using SSL through our server load
balancer. I'd never seen the problem prior to the new SMTP setup and
it goes away if we turn off SSL. Unfortunately, this causes problems
for laptop users since they can't send via wireless or from off-campus
unless they use an encrypted connection on the SSL port (465).

-Robert
 
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