Mulitple Domains

Did you create or update email address policy for the newly added domain (company B)?
if not pls create/update it now

please check this

Yes. I apologize for not mentioning it before but email address policy is in place. Users in Company B are in their own separate OU and email address policy is in effect to that OU.

Did you create MX record for companyB.com domain pointing to the same IP of companyA.com?

if not please create it ASAP

You can test your domainB.com from this
https://testconnectivity.microsoft.com/

Did you add domainB.com in your antispam software/appliance?

domainB.com users receiving internal emails or no?

Have a look at https://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/A_10628-Exchange-2010-host-Multiple-Email-Domains.html
check all settings.

Cheers
Andrew

@ Andrew

I followed the guideline provided by the link to make sure I didn't miss anything and I followed everything exactly as it is. Still not functioning.

@ MAS

As I stated above:

Created an A record to point to Company A External Mail IP
Created MX records to point to Company A MX records

Also Internal email works between user@companyA.com to user@companyB.com and Vice Versa.

This is the NDR I get when I email from outside:

Delivery is delayed to these recipients or distribution lists:

User

Subject: Test

This message has not yet been delivered. Microsoft Exchange will continue to try delivering the message on your behalf.

Delivery of this message will be attempted until 1/23/2014 11:09:34 PM (GMT-06:00) Central Time (US & Canada). Microsoft Exchange will notify you if the message can't be delivered by that time.

What is the result of the inbound test from this site?

https://testconnectivity.microsoft.com/

@ MAS

Only Error Received:

The server returned status code 451 - Error in processing. The server response was: Could not load DRD for domain (companyB.com) rcpt (user@company B.com)
Exception details:
Message: Error in processing. The server response was: Could not load DRD for domain (companyB.com) rcpt (user@company B.com)
Type: System.Net.Mail.SmtpException
Stack trace:
at System.Net.Mail.RecipientCommand.CheckResponse(SmtpStatusCode statusCode, String response)
at System.Net.Mail.RecipientCommand.Send(SmtpConnection conn, String to, String& response)
at System.Net.Mail.SmtpTransport.SendMail(MailAddress sender, MailAddressCollection recipients, String deliveryNotify, Boolean allowUnicode, SmtpFailedRecipientException& exception)
at System.Net.Mail.SmtpClient.Send(MailMessage message)
at Microsoft.Exchange.Tools.ExRca.Tests.SmtpMessageTest.PerformTestReally()
Elapsed Time: 252 ms.

from the outside can you try to telnet test the server with a companyB email address and let us know of any response that is not standard.

See http://www.port25.com/how-to-check-an-smtp-connection-with-a-manual-telnet-session-2/  for a how to and the standard style of responses.

Cheers
Andrew

here is a cut and paste of what i would expect to see. (note the parts that i typed are in bold).

c:\>telnet remote.MyDom.com.au 25
220 remote.MyDom.com.au Microsoft ESMTP MAIL Service ready at Thu, 23 Jan 2014 15
:02:46 +0930
ehlo
250-remote.MyDom.com.au Hello [101.165.121.20]
250-SIZE 104857600
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-AUTH
250-8BITMIME
250-BINARYMIME
250 CHUNKING
mail from: test@testing.com
250 2.1.0 Sender OK
rcpt to: ada@OtherDom.com.au
250 2.1.5 Recipient OK
DATA
354 Start mail input; end with <CRLF>.<CRLF>
this is a test
.
250 2.6.0 <1d4aa44d-db86-416e-88c1-db1a50ee2fb5@MyDomSBS.MyDom.local> [InternalId=
976] Queued mail for delivery

Cheers
Andrew

i have never seen a DRD message from Exchange. This is usually associated with a gateway device. Either smarthost going out, or an incoming proxy (Spam/virus filter).

Can you let us know if there is anything like this in play.

if so can you try a telnet as above, bypassing any gateway device/service.

Cheers
Andrew

@ Andrew

Telnet Output:

220 mail.companyA.com Microsoft ESMTP MAIL Service ready at Thu, 23 Jan 2014 0
0:39:45 -0600
ehlo
250-mail.companyA.com Hello [162.194.18.203]
250-SIZE 104857600
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-AUTH GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250 CHUNKING
mail from:test@testing.com
250 2.1.0 Sender OK
rcpt to:user@companyB.com
250 2.1.5 Recipient OK
Data
354 Start mail input; end with <CRLF>.<CRLF>
This is a test
.
250 2.6.0 <86c67483-895d-4c70-86ec-1a45018fc029@FQDNServer.domain.com> [In
ternalId=53452] Queued mail for delivery

@ Andrew

We are currently using Spam Soap as our Third Party Spam Filter and it is only set for inbound Filtering.

now try the same but in

rcpt to:

use a domain B address

Thanks

@ Andrew

That's what is listed in the Telnet Output above:

rcpt to:user@compnayB.com

sorry i miss-read.
I note that you did send that to user@companyB.com
And i will assume that if that was a genuine email address then you did receive it.

I think you will find your problem is with spam soap.

I am not familiar with their product. but they should have a way of confirming the settings.

Can you let me know if user@companyB.com did receive the message.

Cheers
Andrew

@ Andrew

Email was genuine.

I have access to Spam Soap Admin console so I can remove the inbound filtering to try.

User@companyB.com did not receive the email.

The above telnet, looks like that was to directly to your Exchange server and bypassing spam soap. Can you confirm?

if it was then the exchange accepted the message and queued it, if not delivered within a couple of minutes can you use message tracking in exchange to see what happened to it.

Cheers

@ Andrew

The telnet was a connection directly to the Exchange Server and no message appeared using the message tracking.

Also I have a support case open with Spam Soap to make sure it is nothing on their end.

If the telnet above was directly to the exchange (and it certainly looks that way), then you should have received it.

Can you try the same telnet but to CompanyA and confirm that the message is received.

I suspect that it will work fine for Company A.

With CompanyA and CompanyB address' are they both pointing to the same mailbox?

If not can you check that the CompanyB mailboxes are allowed to receive external emails (see Attached Pic1).

Also disable all (except Recipient filtering) Exchange Antispam filters as per pic2.
1.JPG
2.JPG

Check Hub transport that the Domain is accepted and is authoritive. See Pic3

Sorry meant to add that one before submitting above post.

Cheers
Andrew
3.JPG

Glad to know it is fixed and thanks for adding the solution to EE database

With the guidance on experts here, I was able to work the issue out with Spam Soap Support to determine the real cause of the problem.