Exchange not receiving some emails with attachments.

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?
ScreenFoxAsked:
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Ben HartConnect With a Mentor Commented:
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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Ben HartCommented:
What size are the attachments? What type and speed internet pipe do you have?
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ScreenFoxAuthor Commented:
Some are 50KB while others can reach 2MB, the company's connection is 8MB download  / 8MB upload.
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Ben HartCommented:
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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ScreenFoxAuthor Commented:
I checked and the server does not have a limit set for max reception size (checkbox is not ticked).
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Ben HartCommented:
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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ScreenFoxAuthor Commented:
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 HartCommented:
Also do internal messages with attachments flow freely?
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tmoore1962Commented:
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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ScreenFoxAuthor Commented:
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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