Weird email relay issue

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We've just started having a weird problem in Outlook 2003. You go to send an email and it comes back straight away with a relay denied message. This varies depending on where you are sending the email (as different servers generate different messages for anti-relay). If you send an email to someone else using the same smtp/pop server it works. The server does require authentication, and it's enabled and all set up, but it's like Outlooks is all the sudden trying to send the email straight to the recipient's server rather than relaying off the proper server. Any ideas?
 
Firstly, to my knowledge, Outlook can't act as an SMTP server and attempt to deliver mail directly.

Secondly, even if it could it wouldn't get a relay denied message from the recipient's mail server, as that mail server would be responsible for the domain to which the mail was addressed, so it would accept it. So I think you can rule out that theory.

So it would sound like the SMTP server you've entered is refusing delivery - not quite sure why you're getting different messages though. Could you post some of them, perhaps?

Maybe try a different SMTP server - the ISP who provides you internet access will most probably provide an SMTP server for you to use without any authentication - just go to their website's support section and have a look around.
 
Here’s a couple of the error messages:



The following recipient(s) could not be reached:

'[email protected]' on 29/05/2006 17:11

550 <[email protected]>: Recipient address rejected: User unknown in virtual mailbox table






The following recipient(s) could not be reached:

'[email protected]' on 29/05/2006 17:11

554 <[email protected]>: Relay access denied


Our mail is hosted with fasthosts, and I can send email to any other domain also hosted on fasthosts. When you try and send an email to (say) hotmail, you get a weird user not found on virtual mailbox table message (which is what you would get if you were trying to relay off hotmail’s server). Emailing other domains also gives different ‘relay denied’ messages.

Outlook doesn’t have an SMTP server, but it looks like Outlook is connecting straight to the recipient mail server’s MX to send the mail, rather than just relay the message off my host’s SMTP, as the messages I am getting are the same as if I was to put the recipients MX in as the SMTP server.

I hope this makes sense :) It’s a weird problem, one I’ve not come across before.
 
theMAD2 said:
Our mail is hosted with fasthosts, and I can send email to any other domain also hosted on fasthosts. When you try and send an email to (say) hotmail, you get a weird user not found on virtual mailbox table message (which is what you would get if you were trying to relay off hotmail’s server). Emailing other domains also gives different ‘relay denied’ messages.
It still sounds like the fasthosts SMTP server is the one refusing the relaying. If it was connecting to hotmail's smtp server, then it wouldn't give a relay denied message, as there'd be no relaying involved. Hotmail's MX is responsible for hotmail.com, mail would be accepted.

Outlook doesn’t have an SMTP server, but it looks like Outlook is connecting straight to the recipient mail server’s MX to send the mail, rather than just relay the message off my host’s SMTP, as the messages I am getting are the same as if I was to put the recipients MX in as the SMTP server.
What I mean by Outlook not having an SMTP server is that Outlook can't do that. If it was doing as you suggest, you wouldn't be having any problems as I explained above.

So it's most probably Fasthost's SMTP refusing to relay messages for you. This would explain why you can email to every other Fasthosts domain, as no relaying is involved for those. This is either because it's broken, or because your authentication is setup incorrectly.

So 2 things to try: even though you've checked, check and double check authentication is setup correctly - use documents that are probably available on the Fasthosts website, for example:

http://www.fasthosts.co.uk/knowledge-base/?article_id=320

If it still won't work, change the SMTP server to the one provided by your ISP. Although from the look of your email address, you use btinternet... and I have a suspicion that BT don't provide one.
 
ok I've managed to get it working, really weird though and I still don't know what caused it lol. Quick fix was to change the SMTP server address from mail.domain to smtp.domain (even thought it's supposed to be mail.domain AND this worked on another machine).

Thanks for your help mate!
Dan
 
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