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Exchange 2003 Server can not send email to certain domains (other Exchange servers)

Posted on 2006-11-22
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Last Modified: 2010-03-06
Exchange 2003 Standard Edition.
When my users attempt to reply or send a new message to certain domains, they receive one of the following three messages:

ERROR 1:
This is an automatically generated Delivery Status Notification.
THIS IS A WARNING MESSAGE ONLY.

YOU DO NOT NEED TO RESEND YOUR MESSAGE.

Delivery to the following recipients has been delayed.
       someone@otherdomain.com
       someone2@otherdomain.com

ERROR 2:
did not reach the following recipient(s):
someone@otherdomain.com on Thu, 16 Nov 2006 10:54:17 -0800
    Could not deliver the message in the time limit specified.  Please retry or contact your administrator.

ERROR 3:
Your message did not reach some or all of the intended recipients.
      Subject:  RE: Confirming a couple of deliveries
      Sent:     11/14/2006 9:30 AM

The following recipient(s) could not be reached:
      David Meinert on 11/14/2006 9:41 AM
            You do not have permission to send to this recipient.  For assistance, contact your system administrator.
            <mail.mydomain.com #5.7.1 smtp;550 5.7.1 <someone@otherdomain.com>: Relay access denied>

I had these remote domains check to see if they can resolve the MX record for mydomain.com and they are able to resolve to the correct IP address.  I check http://dnsstuff.com and all records are accurate.

The one thing that seems to be common among all the domains we are having issues with is that they are all using Exchange as well.

Thanks
Mario
0
Comment
Question by:asiuser
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26 Comments
 
LVL 17

Expert Comment

by:upul007
ID: 18000931
Please use www.dnsreport.com to run a report on your domain first. See if there are any issues with your configuration. Pay special attention to items in RED.

The Error 01 is generated according to your server's delay report set up. This is not an Error as such. But it is a good way for the users to know whether their email had been sent or delayed.

Error 02
This can be caused if the Server is not able to send out the email due to heavy traffic on the server itself between the submitted time and until the end of the available sending period. Or this can be caused if the other server does not want to accept the email from your server. The place to check this is Exchange Queues. Send a test email to that domain and FORCE a connection. Exchange 2003 shows a small text message underneath the Queues pane for general info.

The above can be due to your server being listed in Relay Black Lists, Greylists, Open Relay DB's etc.

Error 03.
See if another person can send an email to David and let us know.

Also please use the SpAM DB lookup on DNSSTUFF to check your domain as well.

Good Luck!

Upul
0
 

Author Comment

by:asiuser
ID: 18001118
I ran a report on my domain using www.dnsreport.com and all of the tests passed.

Well I believe the server delay report is set up correctly.  Like I stated in the original question the common thing among the domains that we are having issues with is that they are all using Exchange as well.  I think the issue is related to Exchange to Exchange communications but this is just a theory but I can not find information to back up my theory.

I send a test message and forced the connection, but the message still stayed in the queue.

No one from my domain can send to David, but if I send from a different email domain I am able to get the message to David.  This again adds to fact that I think that issue is related to Exchange to Exchange communications.

Thanks
Mario
0
 
LVL 17

Expert Comment

by:upul007
ID: 18001138
Are you familiar with using telnet to check email issues?
0
 
LVL 14

Expert Comment

by:Ehab Salem
ID: 18001766
If you have recently applied or installed any Microsoft fixes and did not restart your server, restart now and the problems will be solved.

I have had similar problems after applying some hotfixes and everything was ok after the restart.
0
 

Author Comment

by:asiuser
ID: 18004540
I was able to telnet to the other mail server and send a message, but I am waiting on confirmation from the administrator of the other mail server to see if the message was received.  If they did receive the message what would be the next step in the troubleshooting process?

I have also applied all the hotfixes available for my Exchange server and restarted the server.

Thanks,
Mario
0
 
LVL 17

Expert Comment

by:upul007
ID: 18005713
You cannot send to these specific addresses but you do recieve email from them.

Normally any email server should accept emails from another email server. The fact that you can send emails to others is proof that your server is set up correctly. That and the DNS Report.

I have seen this happen when sender filtering is enabled at the recieving side. This can be done for a single sender or the entire domain in exchange. Please check if Davids server had implemented this.

Another scenario is when a server is set up to reject messages from an IP range. You could try setting Outlook or the email client Account settings SMTP to that of your ISP's SMTP server to test sending an email to david. This also needs to be checked.

0
 

Author Comment

by:asiuser
ID: 18005821
That is correct I can receive email from them but they do not receive email from me.

I am glad you brought up the sender filter on the receiver side, I had them check the filter, they decided to turn off all filters to elminate that from the equation.  They said they do not have my IP range blocked.

How do I chang ethe setting my Outlook to use another SMTP server?  When you go to Tool>Email Accounts>View or change existing email account, there is no place to change the setting.

Do you think it has anything to do with Exchange to Exchange communications?  They are saying that they look at the smtp log and that when our Excahange communicates with their Exchange they do not see a QUIT command.  But they do see this command when another Exchange communicates with their Exchange.

Thanks
Mario
0
 
LVL 17

Expert Comment

by:upul007
ID: 18005853
Another thing I forgot to mention was about Firewall or Anti Spam tools which can also block senders or IP ranges. Dont know if that is useful now.

Did you test after they had disabled the sender filter by sending them an email?

When you do go to Outlook > tools > Email Accounts > View or change email accounts and Next - The list of email accounts should be there. You need to highlight the relevent account and press the CHANGE button. Then change the SMTP to what SMTP your ISP had allocated to you. for example mine is smtp.slt.lk which I use in case of emergencies and the ISP had set it up so that I am allowed to relay through their server. If it is not so, please let us know how your email client is set up.

Are there any other applications running alongside Exchange which is integrated with the email sending process? Apart from these Exchange servers which you cannot send to, surely you must be sending to countless other Exchange servers normally? My theory is if you have no issues sending to others, those that do not get emails from you or those that you cannot send to may be having some sort of issue at their end.  
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LVL 17

Expert Comment

by:upul007
ID: 18005864
Just in case you had not tested the email sending using several Telnet methods please refer http://support.microsoft.com/kb/304897
0
 
LVL 17

Expert Comment

by:upul007
ID: 18005869
Did you check whether you are listed in the spam database at www.dnsstuff.com?
0
 
LVL 17

Expert Comment

by:upul007
ID: 18005879
The remark about the other servers not getting the QUIT sort of got me thinking that perhaps something may be interfering with the communication either on your side or the other side.

Please refer http://support.microsoft.com/kb/895857 to see if there is any relevence to your set up or the others if possible.
0
 

Author Comment

by:asiuser
ID: 18005893
I had him check his firewall and he said he is not blocking my IP range.  I did test after he disabled the sender filter, that was one of th efirst steps we took.

I am using Outlook 2003 and my Exchange server is 2003, there is no option to change your smtp server on Outlook when it is configured to connect to Exchange 2003.

There are no other applications running alongside the Exchange when it comes to email sending process.

There are other domains other than David's that I can not send to, I have not been able to contact any of there IT staff to troubleshoot with them.  But the one thing I do know is that all the domains that can not receive email from me is that they are also running Exchange servers.  For this reason, I bring up the fact about Exchange to Exchange communicaiton.
0
 
LVL 17

Expert Comment

by:upul007
ID: 18005911
Please refer the link  http://support.microsoft.com/kb/895857 to see if it similar to your issue.
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Author Comment

by:asiuser
ID: 18005927
We are running a Watchguard Firebox, and we are not running the SMTP proxy like the Microsoft articale states, so I know that is not the issue.  

I also used the telnet method and I am waiting on confirmation from him to let me know if he received it, he will be in tomorrow so I should have an answer regarding if he received the message I sent using the telnet method.

Thanks
Mario
0
 
LVL 17

Expert Comment

by:upul007
ID: 18005948
I am confused. Being a watchguard user myself, how do you allow for the transfer of emails (SMTP traffic) with out a SMTP proxy? Are you using the SMTP Service?

I need to use both. Otherwise some of my emails would not go out......
0
 

Author Comment

by:asiuser
ID: 18005954
I am using Filtered-SMTP, not a SMTP Proxy.
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Expert Comment

by:upul007
ID: 18005966
Just a hunch. Please enable the SMTP Proxy service as well, or was it just called SMTP. The thing was a similar situation happened to me when I had disabled the other SMTP service on watchguard. We were not able to send to certain domains at all. Though I did not figure out if they had Exchange as such.

Wont hurt to try. You could always revert back to the prvious configuration file afterwards if there is no joy!
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LVL 17

Expert Comment

by:upul007
ID: 18005977
Also when you force a connection, what does the Watchguard connection display (the internel items and external items that can be accessed via the Watchguard GUI- I cannot remeber what it is called) show between your Email server and the other side. Also in the first tab, the connection details are listed real time. Does it show the connection being dropped?
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Author Comment

by:asiuser
ID: 18009380
It shows that it is allowing the traffic to go through.  There are no connection drops that appear on the firewall.  Why would I have to enable the SMTP proxy when I have Filtered-SMTP allowing traffic on port 25?
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LVL 17

Expert Comment

by:upul007
ID: 18010196
Like I said earlier, It's just a hunch. there was an oddity about the way that a firebox tackles data packets when it came to email. I also would prefer the Filtered-SMTP due to the ease of setting up what is allowed to get through, but as I said, I did that and it caused a major issue for our staff not being able to email to certain other companies. I had a major time liaising with external ISP's thinking that it was their fault but eventually fixed it by re-enabling the other SMTP service as well as the Filtered SMTP running alongside it. Due to other issues coming through, I never had a chance to figure out why and the time I spent studying the manual was not helpful at all.
0
 

Author Comment

by:asiuser
ID: 18022127
Well according to Watchguard enabling SMTP Proxy would cause additional issues not relieve them since the proxy is more restrictive.  Watchguard stated that the Filtered-SMTP would not affect outbound mail traffic, just allows it to go out.

I also confirmed with the remote party that they did receive the email I sent to them using the telnet method from my Exchange server to their Exchange.

Any other ideas?
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LVL 39

Accepted Solution

by:
redseatechnologies earned 500 total points
ID: 18022541
Is it just a handful of domains?

Consitantly the same domains?

If so, you could use an SMTP connector for these trouble domains, and route it all via your smarthost.

http://www.amset.info/exchange/smtp-connector.asp

-red
0
 

Author Comment

by:asiuser
ID: 18022579
It is a handful of domains, and it is constantly the same ones we are having issues with.  Like I meanted above the common thing among the domains we are having issues with is that they are also running Exchange, which leads me to believe it has something to do with Exchange to Exchange communications.

Mario
0
 
LVL 39

Expert Comment

by:redseatechnologies
ID: 18022594
I would spend no more time on it and just use an SMTP connector with your smarthost.

It isn't a solution to the problem directly, but it will resolve the issue.

-red
0
 

Author Comment

by:asiuser
ID: 18022726
When you are saying smarthost what are you refering to excatly?
0
 
LVL 39

Expert Comment

by:redseatechnologies
ID: 18022763
The process works as follows;

You configure your exchange server to treat certain domains in a different way (this is what the SMTP connector does)

You get it to send these domains via your smarthost (which will usually be your ISPs mail server)

Generally, this is a good solution when you are having troubles sending to AOL or RR or someone who is exceptionally picky about it's senders - OR - when you have having problems with a certain domain and want it fixed quickly.

-red
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