Mail with attachments not being delivered

We are encountering a problem where email with attachments (Word, PDF, etc.) are not being delivered to a specific domain.  Emails without attachments are being delivered.  Attachments are not large.  No could not deliver messages are being returned.

Any suggestions on what this would indicate?
glennsmithntpcAsked:
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MesthaCommented:
If it is a specific domain with the issue, then it would point to the remote domain having the problem.

Simon.
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glennsmithntpcAuthor Commented:
I'd certainly like to put the blame on them.  We have not yet seen any issues with our mail sent to other domains.  So far discussions with domain owner have not progressed to far and they do not believe it to be their issue.  Apparently they are not seeing this problem occur with other senders.  

Any thoughts on what might be causing on their side?
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MesthaCommented:
Sounds like the standard thing. What I refer to as pin the blame on the donkey. Both sides say it must be the other's fault because everyone else is able to send us email.
What I often find is that the other side does have a problem and either the admin
a. Doesn't want to admit that they screwed up
b. Doesn't know there is a problem because no one else has told them.

ISPs are very good at this as well, saying there is no problem with their network and then the problem goes away "on its own" a short time later.

Without an NDR or other log from the SMTP transfer it is hard to say what the problem is. It could be any number of things, including a simple incompatibility between something at your end and theirs, a routing problem, AV or antispam to admin incompetence, where a setting has been changed.

Simon.
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glennsmithntpcAuthor Commented:
What i find most puzzling is that non attachment emails will deliver.  AND they have sent us documents (Word and PDF), i will then forward back to them and it will deliver!  
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MesthaCommented:
That sounds like it might be an antispam filter or something like that. However without an NDR it is hard to say.

The fact that they can send you email means nothing, as most products will allow users to send anything they like out, as they are only looking at stopping inbound.

Simon.
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glennsmithntpcAuthor Commented:
Yes, but my end point on that was that i can forward their originating message with attachment back to them and it will deliver.  Puzzling no?
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MesthaCommented:
Not really - if they originated the attachment then the filter may well have whitelisted it, so that it can recongise the attachment coming back in again.

Simon.
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glennsmithntpcAuthor Commented:
Got it.  

Are you aware of spam filtering criteria that would make attachments fail?
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MesthaCommented:
It depends on the product.
You have nothing to work on. This is like asking a doctor about a friend who is ill and having no idea what any of the symptoms are. There is nothing to work on.

If you are getting no NDRs, then get someone high up in your company to phone someone high up in their company and bang some heads together. Most IT people will simply say it isn't our problem because they want to get rid of you (I did Tech Support for two years, I only had one goal - get you off the phone any way I can).

Simon.
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glennsmithntpcAuthor Commented:
Yeah, call has already been lined up.  Was looking to load up some ammo before the call.

thanks
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