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First off, the relevant environmental information: I'm running Exchange 2007 behind a Barracuda Spam & Virus Firewall 300.

Recently, I've started using a service that sends me a monthly report. Unfortunately, this monthly report comes in an archive that needs to be password protected. Naturally, this led to rejection notifications originating from my Barracuda box (though I suspect they might be straight from the Exchange server, given the plain formatting of the notifications). The odd thing is that I have my password protected archive filter set to quarantine, not block. Furthermore, the blocked mail does not show up in the Barracuda box's message log at all.

To troubleshoot this issue, I've been trying to send a password-protected archive from my personal email addresses to my internal address - I tried whitelisting my personal email addresses both in the Barracuda box and in the Exchange server with

set-contentfilterconfig -bypassedsenders [my address1], [my address2]

but I still got the failure notification when I used my Gmail account, and Hotmail outright rejected the message. (For clarity: this just means Hotmail didn't let me send a message with a password-protected archive attached. It's not unexpected behaviour.)

I even tried

set-contentfilterconfig -bypassedrecipients [my internal address]

but that didn't work either.

Does anyone have any idea what I might be missing here?

Here's the rejection notification:

Delivery to the following recipient failed permanently:

 [my internal address]

Technical details of permanent failure:
Google tried to deliver your message, but it was rejected by the server for the
recipient domain [my domain] by [my Barracuda box's public DNS name]. [My Barracuda box's public IP].

The error that the other server returned was:
552 Password protected zip file found inside of the email

Note that this is different from the usual rejection notifications which look like this:

Delivery has failed to these recipients or distribution lists:

[recipient address]
An error occurred while trying to deliver this message to the recipient's e-mail
address. Microsoft Exchange will not try to redeliver this message for you. 
Please try resending this message, or provide the following diagnostic text to 
your system administrator.

The following organization rejected your message: cuda.[my domain].

Sent by Microsoft Exchange Server 2007 
share|improve this question
1. You don't state what failure message you're getting. It would be helpful to know this. - 2. Your statement "Hotmail outright rejected the message" disagrees with what you're stating is the problem. If Hotmail rejects the message than that's a Hotmail problem, not an Exchange or Barracuda problem. Can you provide more specific information about the problem, like what you're sending from where to where and what failure message you're getting? - 3. I've never heard of the "password protected archive filter " In Exchange. Where in Exchange is that configured? – joeqwerty Apr 24 '13 at 3:11
1. Good point, I'll add the message in. 2. Hotmail gives me a plain rejection message from the Hotmail postmaster address - this is not unexpected, it just means Hotmail doesn't allow me to send password-protected archives . 3. The password protected archive filter is in the Barracuda box, not Exchange. – Seyren Apr 24 '13 at 3:15
up vote 1 down vote accepted

Problem solved. The issue was being caused by SonicWALL's gateway anti-virus.

Note that there's no indication of the SonicWALL having a hand in it; it even uses the Barracuda box's address instead of its own in the delivery failure message.

Here's what I did:

  1. Log in to the SonicWALL.
  2. Go to Security Services > Gateway Anti-Virus
  3. Click the "Settings" button under SMTP
  4. Uncheck "Restrict Transfer of password-protected ZIP files"

I'd like to whitelist certain servers just for the SMTP component, but it looks like I can't. Oh well.

share|improve this answer

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