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Help:  Unable to send mail due to smtp relay issue

Posted on 2007-04-04
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Last Modified: 2008-01-23
I have run into a problem which I just dont seem to find an answer to.  Our exchange server can receive email but for some reason we are unable to send emails.  Every email we send mail to an external domain the email is bounced immediately with the following error message:
There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.  <mydomain.co.uk #5.5.0 smtp;550 relay not permitted>  

I have tried everything I can find to correct this but am unable to find any answers.   Can someone help me figure out what is going wrong.  I have run ExBPA and it finds not errors.  I have run the Internet and Email Config Wizard, again successfully.  Which leads me to believe that what ever is causing my problems is either something very obvious or deep down in the configuration which I am not familar with.  I am running SBS 2003 r2 + Sp2.
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Question by:Fernbank74
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16 Comments
 
LVL 48

Expert Comment

by:Jay_Jay70
ID: 18854528
Fernbank74,

you may well be blacklisted
http://www.mxtoolbox.com/blacklists.aspx

Regards,

James
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LVL 39

Expert Comment

by:redseatechnologies
ID: 18854533
If it is bounced immediately, it is more likely that you are doing something wrong.

Do you have the same issue when using OWA?
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LVL 104

Expert Comment

by:Sembee
ID: 18854550
Do you send your email out directly to the internet or do you use a smart host?
Has it ever worked?

Simon.
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Author Comment

by:Fernbank74
ID: 18856210
I have check with MXTool box and I am not blacklisted.  

The error occurs I use the OWA (assume the web interface for outlook) or a standard outlook client.  I am trying to retrieve the message from the POP3 account from my ISP and send them through their server since I am unable to send them directly to the external domains because I dont have a static IP address.
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LVL 104

Expert Comment

by:Sembee
ID: 18856408
If you are sending email through the ISP, then you should probably speak to the ISP to see if they will allow email from your domain to be relayed through their server. Some ISPs allow anything to go through, others only allow domains that they know about to go through.

Simon.
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Author Comment

by:Fernbank74
ID: 18856485
Thats not really an issue in this case since I can configure a pop3 client to directly send mail through the ISP.  The other reason why I am sure this is not the issue is because my ISP also hosts my website.  

Domain and website hosted by ISP
Mailbox hosted by ISP but sorted locally.
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Author Comment

by:Fernbank74
ID: 18856678
My ISP wont allow SMTP relay on Port 23, 25, 26, 8001, and 2525, which is wht I can send mail.  Is thereway of not relaying the mail but transfering the mail to the ISP mail box so that I can send mail whilst I find an alternative ISP.
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LVL 104

Accepted Solution

by:
Sembee earned 1000 total points
ID: 18856860
Run the Internet and Email Connection wizard and choose smart host when prompted. Enter the ISPs SMTP server. If you need to authenticate then select that as well and enter the required credentials.

What can sometimes happen is that the ISP requires you to authenticate, but uses POP3 to authenticate rather than SMTP. If you are sending only you have to enter credentials.

Simon.
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LVL 6

Assisted Solution

by:manicsquirrel
manicsquirrel earned 1000 total points
ID: 18857201
My ISP, BellSouth, will not allow my server to send out on the SMTP server using mail.bellsouth.net.  Standard mail clients can, like Outlook though.  Sometime ago, I found a newsgroup entry by a Microsoft employee that suggested using the ip address of the ISP's SMTP server and an explaination of what is screwing up.  That solution worked fine for me and three of my customers.

If it helps in any way, the thread was http://groups.google.com/group/microsoft.public.windows.server.sbs/browse_thread/thread/b2b798abb818d698/45af0f85b2cf438a?&hl=en#45af0f85b2cf438a
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LVL 6

Expert Comment

by:manicsquirrel
ID: 18857208
Sorry, as I re-read it seems the guy wasn't a Microsoft employee, but it helped nevertheless.
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Author Comment

by:Fernbank74
ID: 18892118
Thanks that seemed to resolve the problem
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Author Comment

by:Fernbank74
ID: 19367466
Is there any reason why a setting which was working suddenlybegins to revert to the above error.  My system was working but all of sudden after a windows update the above error comes back without any changes to the exchange server.
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LVL 6

Expert Comment

by:manicsquirrel
ID: 19371639
No idea, but you might want to close this question because the issue was resolved over two months ago.  Then you might open a new question and reference this one.
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LVL 6

Expert Comment

by:manicsquirrel
ID: 19371665
Check your SMTP Connector and write down the ip address you have entered.  Re-run your CEICW using your ISP outgoing mail server name.  Next, ping your mail server from a command line.  See if your mail server's ip address has changed from the one you had been using in the SMTP connector.  Lastky, see if using the ISP's mail server name rather than the ip address works now.
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LVL 1

Expert Comment

by:Computer101
ID: 20729459
Forced accept.

Computer101
EE Admin
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