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Exchange not receiving some emails with attachments.

Posted on 2013-05-23
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Last Modified: 2013-06-03
Hello,

I've been having some problems receiving emails with attachments from another company's exchange server.

Whenever someone from that company sends an email with attachments to our server it never reaches it and returns a Email Delayed mail to the sender. If the email is sent without the attachment but everything else is the same, it does arrive without a problem.

I asked guys on the other company to send the same emails (with attachments) to my private gmail account and I received them instantly. And if I send those emails to my company email with my gmail account , I receive it as well.

Any ideas what could be happening here?
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Question by:ScreenFox
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Expert Comment

by:Ben Hart
ID: 39191133
What size are the attachments? What type and speed internet pipe do you have?
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Author Comment

by:ScreenFox
ID: 39191143
Some are 50KB while others can reach 2MB, the company's connection is 8MB download  / 8MB upload.
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LVL 14

Expert Comment

by:Ben Hart
ID: 39191162
Hmm you wouldn't be hitting a limit then with small sizes like that.  But just in case check for the values here: http://social.technet.microsoft.com/wiki/contents/articles/2908.exchange-2010-attachment-size-global-setting-for-send-receive.aspx
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Author Comment

by:ScreenFox
ID: 39191175
I checked and the server does not have a limit set for max reception size (checkbox is not ticked).
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Expert Comment

by:Ben Hart
ID: 39191222
Do you have any sort of spam filters in place?  Barracuda, Sonicwall, etc?  What is between your Exchange server and the interwebs?
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Author Comment

by:ScreenFox
ID: 39191249
Im using the Exchange Spam Filters (Transport Hub) and we have an WatchGuard XTM330 between the Ex server and the internet.
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Ben Hart earned 2000 total points
ID: 39191254
I'd be looking at your WatchGuard box.. that's a likely candidate for introducing 'delays'.. I've never configured one before but def check it;s logs.
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LVL 14

Expert Comment

by:Ben Hart
ID: 39191416
Also do internal messages with attachments flow freely?
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Expert Comment

by:tmoore1962
ID: 39191669
What are the extensions of the attachments, Exchange blocks several file extensions so it may be blocking based on the attachment's file type.
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Author Comment

by:ScreenFox
ID: 39193429
Yeah, no problems with internal messages, and the extensions mostly are pdf files and .doc/.docx files.

I will check its logs and report back.
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