Not able to send Zip files
Hello,
Our users are having issues with sending emails with zip file attachments. I have looked at our exchange server setting and I can seem to find anything that pops out. I also verified our email security gateway and did not find anything. I have not changed anything in our server or Barracuda email security gateway. Below is the error I get. Any help would be greatly appreciated.
Delivery has failed to these recipients or groups:
Starlyn.Sarmiento@amormeus
The email system had a problem processing this message. It won't try to deliver this message again.
Diagnostic information for administrators:
Generating server: xxx.amormeus.org
Starlyn.Sarmiento@amormeus
Remote Server returned '554 5.6.0 Invalid content'
Original message headers:
Received: from xxx.amormeus.org ([::1]) by xxx.amormeus.org
([::1]) with mapi id 15.00.1473.005; Mon, 21 Oct 2019 07:48:36 -0500
MIME-Version: 1.0
Content-Type: text/plain
Date: Mon, 21 Oct 2019 07:48:36 -0500
X-MS-Exchange-Transport-Fr
Message-ID: <c444d4072b8544aaafe8cf98e
Subject: this is a test
Our users are having issues with sending emails with zip file attachments. I have looked at our exchange server setting and I can seem to find anything that pops out. I also verified our email security gateway and did not find anything. I have not changed anything in our server or Barracuda email security gateway. Below is the error I get. Any help would be greatly appreciated.
Delivery has failed to these recipients or groups:
Starlyn.Sarmiento@amormeus
The email system had a problem processing this message. It won't try to deliver this message again.
Diagnostic information for administrators:
Generating server: xxx.amormeus.org
Starlyn.Sarmiento@amormeus
Remote Server returned '554 5.6.0 Invalid content'
Original message headers:
Received: from xxx.amormeus.org ([::1]) by xxx.amormeus.org
([::1]) with mapi id 15.00.1473.005; Mon, 21 Oct 2019 07:48:36 -0500
MIME-Version: 1.0
Content-Type: text/plain
Date: Mon, 21 Oct 2019 07:48:36 -0500
X-MS-Exchange-Transport-Fr
Message-ID: <c444d4072b8544aaafe8cf98e
Subject: this is a test
>>Remote Server returned '554 5.6.0 Invalid content'
As stated this is being blocked by the 'other end'
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As stated this is being blocked by the 'other end'
</p>
ASKER
Remote Server returned '554 5.6.0 Invalid content'
Any executable zipped or special characters on the attachment names? No only xls file and word document. I created the test document and tried sending it to another domain but it bounces back.
are you able to send the same email to different domain like gmail ? Yes, any domain I send to comes back with the same error.
what is the status.. when you send without zip.. I'm able to send without issues.
what is the status when you zip another file to that domain... It bounces back with the error.
do you have any transport rule to defer the message if the server not able to process the message ? I do not have any defer rules.
Any executable zipped or special characters on the attachment names? No only xls file and word document. I created the test document and tried sending it to another domain but it bounces back.
are you able to send the same email to different domain like gmail ? Yes, any domain I send to comes back with the same error.
what is the status.. when you send without zip.. I'm able to send without issues.
what is the status when you zip another file to that domain... It bounces back with the error.
do you have any transport rule to defer the message if the server not able to process the message ? I do not have any defer rules.
It seems remote server is blocking .zip format files. You need to contact remote server admin.
ASKER
Hello Amit,
It happens to all domains not just this one.
It happens to all domains not just this one.
Check your outbound rules on the Barracuda.
It happens to all domains not just this one.
Please clarify... 1. Do you mean it happens no matter what domain you send to? Or 2. the same thing happens for any message sent to this domain from any location?
If #2, you might save yourself some time and contact the mail admin at the recipient domain and check if they are blocking ZIP files.
I had a problem like this once with larger zip files because the mail gateway had to unzip them to scan them and they went over the size limit.
Check header information and see from which server or ip it is getting rejected.
ASKER
Brian,
it happens to any domain I send email. I tried it to my gmail, yahoo, other domains that we work with. I know for sure one domain is blocking zips so that one I'm not worried about. I tried sending it to someone in my own domain and it wont deliver.
it happens to any domain I send email. I tried it to my gmail, yahoo, other domains that we work with. I know for sure one domain is blocking zips so that one I'm not worried about. I tried sending it to someone in my own domain and it wont deliver.
Do messages that stay within the domain go through the Barracuda?
ASKER
Amit,
It gets rejected at our server. It does not make it to our Barracuda email gateway. I'm thinking it has to do with our exchange server but I don't know what exactly. I have no deferred policies and I have not made any changes recently. It started all of a sudden.
It gets rejected at our server. It does not make it to our Barracuda email gateway. I'm thinking it has to do with our exchange server but I don't know what exactly. I have no deferred policies and I have not made any changes recently. It started all of a sudden.
Check your transport rules.
ASKER
Masnrock,
I checked the transport rules and found nothing that would be blocking it. I only see forwarding rules. If I send a zip file on my domain it also fails. I renamed the file extension and it seems to send it.
I checked the transport rules and found nothing that would be blocking it. I only see forwarding rules. If I send a zip file on my domain it also fails. I renamed the file extension and it seems to send it.
Which version of Exchange?
ASKER
I'm using Exchange 2013.
Take a look in attachment filtering?
The error '554 5.6.0 Invalid content' usually means it couldnt be processed, not that it was actively blocked. We need ot identify which server/service is having trouble so we can focus on the right area.
Which server is: xxx.amormeus.org in the message 'Generating server: xxx.amormeus.org'
Is this your server, the barracuda or something else?
if it's yours, where does mail go next? do you send via a smarthost or mail filtering company, or does it go direct to the recipient?
Which server is: xxx.amormeus.org in the message 'Generating server: xxx.amormeus.org'
Is this your server, the barracuda or something else?
if it's yours, where does mail go next? do you send via a smarthost or mail filtering company, or does it go direct to the recipient?
ASKER
Steve,
The server xxx.amormeus.org is our exchange server. Internal email goes to our exchange email and never touches the barracuda. If it's external, it first goes to the exchange server then the barracuda and our to the recipient.
The server xxx.amormeus.org is our exchange server. Internal email goes to our exchange email and never touches the barracuda. If it's external, it first goes to the exchange server then the barracuda and our to the recipient.
I presume you have Exchange 2013 SP1. You need to look at the attachment filter on your Exchange Server.
ASKER CERTIFIED SOLUTION
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ASKER
masnrock,
Yes, we have Exchange 2013 SP1. I checked all attachment filters and I found nothing that states zips are being blocked. One thing that I did find is that if I rename the extension to something else, the email does deliver. It's only zip that doesn't. It stops at the Exchange server because it never makes to the barracuda for externals or to the internal recipient.
I also, checked the rules and found nothing that shows zips being blocked. We have some forwarding rules but that's about it. I checked the protection tab and it only shows a malware rule but nothing about zips.
Yes, we have Exchange 2013 SP1. I checked all attachment filters and I found nothing that states zips are being blocked. One thing that I did find is that if I rename the extension to something else, the email does deliver. It's only zip that doesn't. It stops at the Exchange server because it never makes to the barracuda for externals or to the internal recipient.
I also, checked the rules and found nothing that shows zips being blocked. We have some forwarding rules but that's about it. I checked the protection tab and it only shows a malware rule but nothing about zips.
ASKER
Steve,
Yes we do have an AV on our exchange server. Let me check that.
Yes we do have an AV on our exchange server. Let me check that.
SOLUTION
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ASKER
Thank you all!! It ended up being the AntiVirus which was blocking the zip file.
Remote Server returned '554 5.6.0 Invalid content'
Any executable zipped or special characters on the attachment names?
are you able to send the same email to different domain like gmail ?
what is the status.. when you send without zip..
what is the status when you zip another file to that domain..
do you have any transport rule to defer the message if the server not able to process the message ?