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sent emails with attachments vanish from Eudora POP client

Hi There,

I'm having a weird and wild problem.
We have a Mac Eudora POP client on our LAN. When we try to forward certain emails with European MS Word documents, the emails appear in the Eudora Sent mailbox, but don't make it to their destination to a local user in our domain.

Copies of the same emails can be forwarded successfully within the domain from Windows machines running Outlook Exchange clients.

I've got journalling turned on, and I'm not seeing the emails forwarded from the Mac POP client.

Your help will be greatly appreciated!

Thanks, Kristin

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redseatechnologies

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ASKER

Hi Red,

We do have spam filters, but I checked and didn't find the emails in any of the Spam folders.

Any other ideas about how to troubleshoot this?

How can I check to see if the Eudora client successfully sent an email through Exchange server?

thanks, Kristin

redseatechnologies

You could check if it ever hit the Exchange server using message tracking.

http://www.msexchange.org/tutorials/Exchange-2003-Message-Tracking-Logging.html

What spam filter do you have?

Can you get this user to send via the ISPs SMTP server as a test?

Vishal Breed

http://support.microsoft.com/kb/843105/en-us

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ASKER

Hi Red,

Thanks for the link to the message tracking info. I've now determined that these particular emails are leaving my Mac Eudora client and are hitting the Exchange server. However, they are still apparently vanishing. I mean, they are not being received by their rightful local recipients.

The spam flagging software that we use is called GFI MailEssentials. It is set to FLAG the spam (prepend the word "SPAM:..." to the offending message subject header. I've double-checked to make sure the MailEssentials is NOT set up to delete any email.

What would you suggest that I do to troubleshoot this now?

Thanks! Kristin

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ASKER

re: testing these messages using the ISP's SMTP server
I'll look into this now.

thanks, Kristin

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ASKER

OK, I've gotten a little closer to solving the problem. I know what's happening, but don't know how to resolve it:
I believe that this problem is only occuring with MS Word documents that have a "-" in the name, which are being forwarded from a Mac Eudora client. The same attachment with the same name, for instance "VIVE003-6.doc" is forwarded without problems from a Windows Outlook mail client.

These documents are being emailed to us and then we need to forward them internally.
Is there a fix for this problem, short of changing the document names?

Thanks! Kristin

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ASKER

Hi Red,

I think that my question has grown here. I'm going to go ahead and award you the points for this question and start a new one with the new info that I have.

Thanks again for your help!

Best Wishes, Kristin

redseatechnologies

Thanks Kristin, glad I could help

-red

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ASKER

Hi Red,

It turns out that the problem was with TrendMicro virus protection software. I discovered that some of the attachments that we were receiving on the Mac were infected. Somehow they got through the virus protection at the Exchange level on the way in to the Eudora client.
But the same emails forwarded from the Mac client to a PC Outlook client were getting deleted by the virus protection software.

Now I just have to make sure that viruses are getting cleaned by the Mac or by the software on the Exchange server before they get to the Mac Eudora client.

Thanks Again, Kristin