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22-04-2008, 15:54   #1
onechewy
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550 SMTP Relay Error in Outlook

One of the lads here in work has got both his work mail and his NTL (*@upcmail.ie) set up in Outlook. He can send mails perfect from his work address, but when sending mails from his upcmail, 99% of them return a 'System Administrator: Undeliverable' Error. The error mail contains the following: 'The following recipients cannot be reached: 'xxxxx@gmail.com' on 22/04/2008 15:28 550 relaying mail to gmail.com is not allowed.

This happens regardless of the domain I send it to, or if the 'my server requires authentication' box is ticked in the account settings. It's Outlook 2007 he's using, and the work mail is IMAP. The annoying thing is that if I change the settings, like untick or tick the aforementioned box, sometimes a mail will send fine and then two minutes later it won't send again.

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22-04-2008, 17:09   #2
darraghrogan
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What SMTP server is he trying to send using? He may be sending emails from his upcmail.ie address through your SMTP server, which is rejecting him as he isn't on your domain, or, he may be trying to send using UPC's smtp server, which is rejecting him because his message isn't coming from a UPC IP address.

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23-04-2008, 10:40   #3
onechewy
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Thanks for the reply Daragh,

I have the two accounts set up completely seperately in Outlook with the UPC mail having pop3.upcmail.com and smtp.upcmail.com as it's mail servers. We have our work mail server on site here so the IMAP account is pointed at the IP address of our router and I can send and receive mail just perfect from that.

Anyways, I deleted the IMAP account, cleared out any temp files just in case, and with only the UPC mail account setup in Outlook, I'm still getting this stupid 550 smtp error.

So it's something to do with just the upcmail account.
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23-04-2008, 12:01   #4
FruitLover
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What server is returning the 'System Administrator: Undeliverable' errors? You may need to check the headers. You could also telnet to port 25 on the upcmail server and try sending a mail manually (look up SMTP in wikipedia or some such for SMTP commands).

I'd imagine the upcmail server is not allowing you to relay through it, as darraghrogan explains above.

Last edited by FruitLover; 23-04-2008 at 12:03.
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23-04-2008, 14:40   #5
onechewy
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Problem solved!

I didn't know that you've to change smtp settings according to what network you're using, so in order to send mail out of our network, I've to use our smtp server here. I put in our outside IP address for the smtp server and authenticated it using his work mail logon details. Works fine, and I'm presuming that should work fine wherever he brings his laptop?

Thanks for the replies. FruitLover, the 'System Administrator: Undeliverable' messages are Outlook errors as far a I know. They're the ones that appear with a little red icon beside them, and they appear when Outlook can't send email for whatever reason. They appear instantaneously in your inbox. pesky blighters...

Gone now though!
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24-04-2008, 22:24   #6
FruitLover
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Quote:
Originally Posted by onechewy View Post
Problem solved!

I didn't know that you've to change smtp settings according to what network you're using, so in order to send mail out of our network, I've to use our smtp server here. I put in our outside IP address for the smtp server and authenticated it using his work mail logon details. Works fine, and I'm presuming that should work fine wherever he brings his laptop?
This will probably not work for all domains - upcmail.ie has an SPF record, which some mail servers/relays/filters will look up when they receive a mail claiming to be from a upcmail.ie address. If they do, and the sending server is not contained within the domain's SPF record as an authorized IP (for example if it's sent from your work mail server), then it will block the mail (or junk it, depending on how both the SPF record and mail filter are configured).

A lot of people still don't use SPF checking (and upcmail.ie's record is set to softfail, which some mail servers will pass), so you'll get mails through to some domains, but chances are you'll get mails blocked to a lot of others (and you might not even get a bounce message to let you know that it was blocked).

Last edited by FruitLover; 24-04-2008 at 22:32.
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24-01-2013, 18:39   #7
Dinarius
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I'm having a similar problem with Outlook 2010 via UPC.

These are two typical errors....

Server error: '550 5.1.1 Relaying denied to domain ria.ie'

and......

Server error: '550 5.1.1 Relaying denied to domain yahoo.co.uk'

Could someone please tell me in small steps(!) how to fix this problem?

Many thanks.

D
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