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Exchange SBS 2003. Issues sending external mail

Posted on 2014-01-02
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Last Modified: 2014-01-03
Hello, I've been having some difficulties with our Exchange server on SBS 2003.  We finally resolved the issue we'd been having with receiving external emails and our Exchange was fully working as of last week. However, upon returning this week we found that we could no longer send emails to external sources. The errors we have been receiving, for all email accounts through both telnet and outlook, are 501 5.5.4 or 550 5.7.1 when we try to send mail. This effects all users.

I have spent the last week trying to figure out what may have caused this and have looked at all the usual solutions for this error, with no luck. Our SMTP connectors appear fine. I've tried adding a new recipient policy. I've disabled our anti virus software. Our firewalls have both been disabled (temporarily) and the problem still occurred.

If anyone has any ideas, I would really appreciate it. Thanks.
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Question by:AndyWhy
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Expert Comment

by:Will Szymkowski
ID: 39751416
When you look at the eamil header does the email leave your Exchange server or are these messages being generated from your Exchange server?

Have you checked the application logs on your Exchange Server?

You can also check https://testconnectivity.microsoft.com/ to a series of test to ensure that everything is operating accordinly.

Will.
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Expert Comment

by:Alan Hardisty
ID: 39751418
Can you send any mail out from your server?  If not, can you telnet to my server (from a command prompt):

telnet mail.sohomail.co.uk 25
or
telnet 46.65.213.106 25

If not, talk to your ISP as they may be blocking port 25 outbound for you.  Also check your firewall allows outbound port 25 too!

If you can send some emails, please check my article:

http://www.experts-exchange.com/Software/Server_Software/Email_Servers/A_2427-Problems-sending-mail-to-one-or-more-external-domains.html

Alan
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Expert Comment

by:Diwakar Sharma
ID: 39751426
Open the Exchange System Manager;

Go in Administrative Groups -> Administrative group name -> Server -> Server name -> Protocols -> SMTP;

Right click on Default SMTP Virtual Server -> properties;

Access tab -> Relay buttom;

Select "only the list bellow" and add your domain and\or IPs you do want to allow the relay

 and finally check  the "Allow all computers witch successfully authenticate to relay, regardless of the list above" checkbox.
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Expert Comment

by:Diwakar Sharma
ID: 39751432
Also let me know if you are using any smart host to relay emails.

Diwakar
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Expert Comment

by:Alan Hardisty
ID: 39751549
Ignore the relaying instructions mentioned above by Diwakar.

This is SBS and you should be using the Wizards not manually tweaking the settings and there is no need to relay.

If you need to change anything, run the Connect to the Internet Wizard and follow the prompts there to setup your email flow.

Alan
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Author Comment

by:AndyWhy
ID: 39753471
Will- they are being generated by Exchange. When you say application logs, do you mean the logging I've set up for Exchange? For whatever reason, the logging doesn't seem to have any listings for emails I've attempted to send out. Just used that link you suggested and my incoming and outgoing SMTP both tested fine. Must be something server side.

Alan- I was able to telnet onto your server ok. It seems that this is effecting all of the external domains I'm trying to send messages too.

Diwakar- I tried that already and it made no difference. Also, I'm not using a smart host.

I really appreciate all the help so far! Thanks!

After disabling our anti virus yesterday, the undeliverable emails have changed . Previously, we would receive an email with the 501 5.5.4 or 550 5.7.1 errors almost immediately. Now it seems to be bouncing around in our server for a few hours and is now giving a totally different error-    

 A configuration error in the e-mail system caused the message to bounce between two servers or to be forwarded between two recipients.  Contact your administrator.
            <www.roselodge.co.uk #4.4.6>

Though when I tested it again this morning, I got 501 5.5.4 error again... This is all very strange.
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Expert Comment

by:Will Szymkowski
ID: 39753508
Do you have a smart host which is sending your external messages? If you do you may want to check this. Also when you send an email externally check the queues on exchange to see what route your message is taking. It should also provide an error message there as well when it fails.

If you can receive email internally and externally then receive connectors are fine. If you have trouble externally and it is not leaving your exchange server then it is most likely a send connector issue. Has there been any firewall changes recently which would stop exchange from talking to a smart host or appliance in the DMZ?


Will.
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Expert Comment

by:Alan Hardisty
ID: 39753522
What AntiVirus software have you got installed?
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Author Comment

by:AndyWhy
ID: 39753528
Ok, it seems that our SMTP connector was pointing to our internal mail server as a smart host, which was causing the messages to bounce around the server before eventually spitting out a NDR. I can now send to most domains I have checked, however, I still get this error-

         The e-mail account does not exist at the organization this message was sent to.  Check the e-mail address, or contact the recipient directly to find out the correct address.
            <www.roselodge.co.uk #5.1.1>

When I try to send to gmail. I've tried updating the recipient policy to add in @gmail.com and gmail.co.uk, but it still keeps happening. I'm glad that the main issue is sorted though!
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Expert Comment

by:Will Szymkowski
ID: 39753537
That is great news. The other issue you are having might be due to AutoComplete. Do the following...
- Open Outlook>New Email
- start typing the email address
- you will see the email address below start to populate below
- beside the email address there is an "X"
- click the "X" and remove it
- type the email address in manually again

This usually happens when you move mailboxes to another site or another mailbox. Because your smart host was internal i am wondering if this had the same issue with auto complete.

Will.
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Author Comment

by:AndyWhy
ID: 39753564
Thanks Will, I've tried that as well when I was first attempting to troubleshoot this issue, but I kept getting the same error. It only seems to be with gmail too.
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Accepted Solution

by:
Will Szymkowski earned 500 total points
ID: 39753582
Is it making it outside your Exchange server or is this another internal error message? Do you have any transport rules for this domain? Also did someone mistakenly add Gmail.com as an "Accepted Domain" in your environment? Might be a long shot but figure i would ask.

Will.
0
 

Author Comment

by:AndyWhy
ID: 39753647
Yep, that's exactly what it was! My mistake- recipient policies are still pretty new to me!

Thanks for everyone for all your help!
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Author Closing Comment

by:AndyWhy
ID: 39753651
Everyone who offered help in this thread was extremely helpful and nice. Really gave me a good impression about the forum. Thanks again guys!
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LVL 1

Expert Comment

by:Diwakar Sharma
ID: 39753654
Hi Andy,

You can verify email address of recipient by using below link.

http://verify-email.org/

Diwakar
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