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Unable to send email to other domain #5.5.0 smtp;500 Firewall Error

When I try to send an email to an external domain, I receive this error message:

There was a SMTP communication problem with the recipients email server.  Please contact your system administrator. <ourdomain.local #5.5.0 smtp;500 Firewall Error>

What does this mean? This only occurs when I send emails with attachments.
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katredrum
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katredrum
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1 Solution
 
TK-77Commented:
Check your SMTP settings. You may have to select "My Outgoing Server (SMTP) Requires Authentication.

TK
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katredrumAuthor Commented:
TK, Are you referring to Outlook 2007 or on Exchange Server 2007?
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katredrumAuthor Commented:
I don't know of any SMTP settings in Outlook 2007.
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katredrumAuthor Commented:
Does anyone know if this issue is on my side (Exchange Server or Router) or the destination's (Exchange Server or Router)? I am trying to narrow down where the problem could lie.

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katredrumAuthor Commented:
qiltjr, your second link is more like what I am experiencing. I also have a Cisco 1760 and use CBAC. The only SMTP inspection occurs from inside to outside. I have disabled this and will try.


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katredrumAuthor Commented:
Cisco CBAC SMTP inspection generated this error. Apparently ip inspect smtp doesn't work well with Exchange Servers.
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