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My boss sent out an email from my Exchange 2010 org and attached a PDF and a Word doc to it. He came back the next day and told me that some of the 8 or 10 people that received this email could open up the attachments no problem. The other 2 or 3 people, could not.

One of these people who could not open the attachment, went so far as to call Comcast (his email service provider) and ask them where his attachments went. Comcast told this person that when they received the email, the attachment was 0 bytes in size.

This may sound like more of a rant than a question but I'm genuinely concerned. Is there any possible way that something could have gone wrong on my end that sent out the email to some with the attachment and to some without?

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3 Answers

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This one will be interesting. I would start by getting the list of users he sent it to, and figuring out which ones for sure didn't get the attachment. See if there's anything in common with the addresses (are they going to the same email host?) If the email addresses are publicly accessible (Comcast, Hotmail, etc) see if you can get a few to test and replicate.

You say that Comcast talked to the guy, they said that the attachment was 0 bytes in size. Does that mean that they saw something was attached but contained no data, or that there was no attachment at all?

Get logging set up on your server. When you send out test messages, track them and see what it says. If you have logging set up already, see if you can look at the message your boss sent out. Is there anything out of place about it if you can see the logs?

I know this is kinda general and all, but it's how I would start to approach it. Comcast has been known to suck emails into a giant blackhole and never notify anyone, so take that for what it's worth.

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How big were the attachments? If the combined total, with the email message size exceeded the receiving servers limit, then it could well have trimmed them.

Most email servers have message size limits. Also, the recipients may well have mailboxes that are near capacity.

Possibility of attachments being infected and stripped, or the email flagged as spam and attachments stripped. There could be a sending error, but it's unlikely if many recipients received correctly from the same send, from the same server.

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Most email systems I know would bounce the whole message back if it exceeds the recipient limit, and not strip anything. Or have something saying that the attachment wasn't downloaded automatically for fear of a contaminated file. But it wouldn't mangle the message like what you're suggesting. –  Holocryptic Mar 19 '11 at 0:36
    
@Holocryptic: Depends on the configuration. I've known plenty of servers to strip attachments over the years. –  Orbling Mar 19 '11 at 7:12
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We've had a comparable issue already using Exch2K7 - as our users were/are using quite different email clients (on Windows, OS X, Linux..) and found a solution that still works for our Exch2K10. You may try out those settings:

`EMC -> Organization Configuration -> Hub-Transport -> Tab: Remote Domains -> right click & properties on your definition -> Tab: Message Format:

Exchange rich-text format [x] never use

Character Sets Both 'Western ISO' (in my case)`

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PS: To clarify: In my case the users didn't got a 0 byte attachment while Exchange rich-text was enabled. But they've got a binary attachment that they couldn't open in any way. –  desasteralex Mar 19 '11 at 2:34
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