Joe S. wrote:
Here's more information that I should have added with the original email:
1) All attachments are under the 20mb limit, my users regularly send attachments to these same clients without any trouble 2) Server is Centos 5.3 running all up to date packages, nothing was changed/modified before this issue started happening 3) Looking through send logs shows a few differences in the errors but all seem similar: Connected_to_x.x.x.x_but_connection_died._(#4.4.2)/
Connected_to_x.x.x.x_but_connection_died._Possible_duplicate!_(#4.4.2)/
Connected_to_x.x.x.x_but_connection_died._broken_pipe_(#4.4.2)/
Connected_to_x.x.x.x_but_connection_died._timed_out_(#4.4.2)/

Try setting up recordio on the process and watching the logs then to see where the issue lies.
Does the bouncing with attachments only happen with 1 external server?
Do you run all of your users through spamassassin/clamav when they send emails? From what you've shown and the information you've given it looks like the other server is having problems and it may not be your system at all. But if it happens to all outgoing mail with attachments (to multiple domains/servers) then it requires more investigation on your end.

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