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Trouble exchanging email with one customer???

I have a new customer that has an office less than a mile from my office. We both use Bellsouth DSL. For some reason I cannot receive his email unless he replies to an email that I sent. I realize that distance has nothing to do with this but it just makes it more frustrating. Sometimes he does not receive my email unless I am replying to an email from him. I don't seem to have this problem with any other customer. What could be the problem? Is there something in our signatures that is triggering the spam filter? How do we force exchange/outlook/OE to trust each others address?

I use Outlook, ISA, Symantec Agent for Exchange. My client uses Outlook Express.

Thanks.
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ArkAdmin
Asked:
ArkAdmin
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2 Solutions
 
war1Commented:
Greetings ArkAdmin !

If the email is being flagged as spam, add address to Outlook Safe Sender list.  Outlook Express does not have a safe sender list.

Check the Bellsouth webmail.  It may have a spam filter.  Put your respective addresses in the sapm filter white list.

Best wishes, war1
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ArkAdminAuthor Commented:
Actually, i didn't mention it  but i receive incoming mail through my domain host not bellsouth. My customer does use a bellsouth email address however. I'll have him check his bellsouth webmail.
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ArkAdminAuthor Commented:
I just sent an email to the customer as a reply to an email from him.
I received an email back from the mail delivery system stating the following...

The following message to <mango@bellsouth.net> was undeliverable.
The reason for the problem:
5.1.0 - Unknown address error 502-'Command not implemented'

The original message was attached along with a text file named ATT04858.txt stating the following...

Final-Recipient: rfc822;mango@bellsouth.net
Action: failed
Status: 5.0.0 (permanent failure)
Diagnostic-Code: smtp; 5.1.0 - Unknown address error 502-'Command not implemented' (delivery attempts: 0)
Reporting-MTA: dns; mx00.mail.bellsouth.net

I have changed the actual email address of the customer.
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war1Commented:
Is mango @ bellsouth.net the corect customer address?  Check if customer is blocking your address or you domain.
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ArkAdminAuthor Commented:
yes, the address is correct, i'll check about the blocking.

something just occured to me, i have a hotlink to the free autodesk ADR program in my email signature. i just had another customer tell me that our email was getting snagged in their spam filter. is there something about a html hotlink like this that could increase the chances of the email getting blocked? and also, why do i and the customer receive no notification how or why the email was blocked?
Thanks again.
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war1Commented:
Some spam filter will flag emails with links as spam.  That is too agressive filtering, in my opinion. But everyone is trying to fight spam.
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omaadaptmarkCommented:
That bounce back is usually an issue with the email client.  I'd recommend trying a different client or webmail to see if you can duplicate the problem.  Based on that bounce back and that error categorization, the message is being handled incorrectly by the client (Outlook).  This can be simply a bad client or the client handling a particular part of a message - attachment, link, embedded image - out of line of the RFC.  The receiving mail server, if configured correctly, will not accept something non-standard.
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war1Commented:
ArkAdmin, any update?  Did you check if customer is blocking your domain?
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