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Exchange 2013 mailbox additional smtp address 5.1.1

Hi,

I've created a multi-tenant Exchange 2013 environment and have created a couple of mailboxes for testing.
A user from domain abc.com has an address user@abc.com and an additional smtp address user1@abc.com setup by the applicable EAP.
Another user from domain 123.org has an address user@123.org and an additional smtp address user1@123.org setup by the applicable EAP.

Now, these 2 users can email and reply between each other using either user@ or user1@ addresses. The issue comes when I use an external domain from the system altogether and attempt to email their user1@ addresses, I get the following NDR:


Delivery has failed to these recipients or groups:
user1@abc.com
The email address you entered couldn't be found. Please check the recipient's email address and try to resend the message. If the problem continues, please contact your helpdesk.


Diagnostic information for administrators:
Generating server: HEXS01.testdomain.local
user1@abc.com
Remote Server returned '< #5.1.1 smtp;550 5.1.1 RESOLVER.ADR.RecipNotFound; not found>'

But these work internal of the HEXS01 server...just not when an external user tries to email the user1@ addresses. When an external user tries to email the user@ addresses they're delivered with no issues.

Any ideas?
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purpleoak
Asked:
purpleoak
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1 Solution
 
dsnegi_25decCommented:
are you using any type of gateway like FOPE or Postini if yes are they listed there or not
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purpleoakAuthor Commented:
No, no fope or postini
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Will SzymkowskiSenior Solution ArchitectCommented:
Is this a new build or a migration? does this happen with any other account or just this account?

Take a look at the below KB article for troubleshooting details..
Delivery has failed 550 5.1.1

Will.
0
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purpleoakAuthor Commented:
Hi Will, this is a new build, not a migration
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ktaczalaCommented:
What do you have list in your accepted domains?
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purpleoakAuthor Commented:
Within the example the correct domains: 123.org, abc.com as well as a default system one hostedexchange.com for arguments sake.

Interesting thing happened with testing earlier today, when switching the default address to user1@ it threw up the 5.1.1 error, but when switching it back it would only issue 5.1.1 for the user@ that traditionally always worked. I then had to recreate another test user before I could get anything working.
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ktaczalaCommented:
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purpleoakAuthor Commented:
Thanks for the link but I have already performed all of those tasks during the customer and user setup. I've attached from screenshots to give you an idea.

I can email firstname.lastname@fiveringsit.co.uk but can't email flastname@fiveringsit.co.uk:

Delivery has failed to these recipients or groups:

flastname@fiveringsit.co.uk
The email address you entered couldn't be found. Please check the recipient's email address and try to resend the message. If the problem continues, please contact your helpdesk.








Diagnostic information for administrators:

Generating server: OES001.outboundemail.local


flastname@fiveringsit.co.uk
Remote Server returned '< #5.1.1 smtp;550 5.1.1 RESOLVER.ADR.RecipNotFound; not found>'


Original message headers:

Received: from OES001.outboundemail.local (192.168.10.30) by
 OES001.outboundemail.local (192.168.10.30) with Microsoft SMTP Server (TLS)
 id 15.0.516.32; Sat, 1 Feb 2014 20:44:22 +0000
Received: from smtp96.iad3a.emailsrvr.com (173.203.187.96) by
 OES001.outboundemail.local (192.168.10.30) with Microsoft SMTP Server (TLS)
 id 15.0.516.32 via Frontend Transport; Sat, 1 Feb 2014 20:44:22 +0000
Received: from localhost (localhost.localdomain [127.0.0.1])      by
 smtp13.relay.iad3a.emailsrvr.com (SMTP Server) with ESMTP id 9CC3912809C      for
 <flastname@fiveringsit.co.uk>; Sat,  1 Feb 2014 15:44:54 -0500 (EST)
X-Virus-Scanned: OK
Received: by smtp13.relay.iad3a.emailsrvr.com (Authenticated sender:
 smtpsender-AT-5ringsgroup.co.uk) with ESMTPSA id 0B542128091      for
 <flastname@fiveringsit.co.uk>; Sat,  1 Feb 2014 15:44:54 -0500 (EST)
Received: from 5RGS003.5rings.local (172.16.0.14) by 5RGS003.5rings.local
 (172.16.0.14) with Microsoft SMTP Server (TLS) id 15.0.620.29; Sat, 1 Feb
 2014 20:44:36 +0000
Received: from 5RGS003.5rings.local ([::1]) by 5RGS003.5rings.local ([::1])
 with mapi id 15.00.0620.020; Sat, 1 Feb 2014 20:44:36 +0000
From: Toby Kershaw <Toby.Kershaw@5ringsit.co.uk>
To: "flastname@fiveringsit.co.uk" <flastname@fiveringsit.co.uk>
Subject: test
Thread-Topic: test
Thread-Index: Ac8fjmn0pJayES9hQ+Wskbn4hkjudQ==
Date: Sat, 1 Feb 2014 20:44:35 +0000
Message-ID: <655ce26a9ad54da4ab999aaa095653ef@5RGS003.5rings.local>
Accept-Language: en-GB, en-US
Content-Language: en-US
X-MS-Has-Attach: yes
X-MS-TNEF-Correlator:
x-originating-ip: [172.16.0.124]
Content-Type: multipart/related;
      boundary="_004_655ce26a9ad54da4ab999aaa095653ef5RGS0035ringslocal_";
      type="multipart/alternative"
MIME-Version: 1.0
Return-Path: Toby.Kershaw@5ringsit.co.uk
accepted-domains.jpg
EAP.jpg
test-user.jpg
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ktaczalaCommented:
I tested your issue by adding a second e-mail to one of my domain accounts.  Everything come thru just like it's supposed to.
from external e-mail it works too.

make sure there's no unnoticed typos
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ktaczalaCommented:
Only thing I see in your that's different than mine is the EAP
I only have the default policy.
SMTP
primary: @domain.com
secondary: @domain.local
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ktaczalaCommented:
yours has:
john.smith@fiveringsit.co.uk
jsmith@fiverings.co.uk

maybe that's you issue.
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purpleoakAuthor Commented:
Just double checked and it's got the correct domain fiveringsit.co.uk,
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purpleoakAuthor Commented:
To make matters confusing, if I use my gmail account to test firstname.lastname@fiveringsit.co.uk and flastname@fiveringsit.co.uk it sends successfully.
If i send to those same addresses from my actual exchange 2013 server in the office it produces the 5.1.1 for just flastname@fiveringsit.co.uk.

Ktaczala could you try sending an email to those 2 email addresses and let me know if you get a bounceback?
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ktaczalaCommented:
ok, just sent message to each. will let you know if I get NDR.
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purpleoakAuthor Commented:
And you're using an Exchange 2013 box to send those? I've received them both :S
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ktaczalaCommented:
yes exchange 2013
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purpleoakAuthor Commented:
With this testing then it seems more like the issue is with my internal exchange 2013 box and not the multi tenant box I've setup....?
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ktaczalaCommented:
Let's recap.  The way it is right now.  How can you make it fail?
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purpleoakAuthor Commented:
I can make it fail by emailing flastname@fiveringsit.co.uk from my toby.kershaw@5ringsit.co.uk address. but the same test from gmail works...is this to do with my own cache of the recipient? If so...how do I make this go away for someone who has emailed flastname@fiveringsit.co.uk before?
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ktaczalaCommented:
In outlook clear your suggested list
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purpleoakAuthor Commented:
I've cleared it but it's still failing.
I don't understand why I get 5.1.1 because that points to the remote server (my new multi tenant box) as the server having the issue.
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ktaczalaCommented:
Try running tests here see if it shows anything
https://testconnectivity.microsoft.com/
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purpleoakAuthor Commented:
Ok, as far as I can tell it is my internal on premises Exchange 2013 box...not my hosted one I've created. Using the testconnectivity link fails as Rackspace blocks it (at the minute the mx records point there). Anyone got any ideas on what would cause this kind of failure?
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purpleoakAuthor Commented:
After testing I can send to the default domain on the hosted environment but I can't send to the alternative domains on there.
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ktaczalaCommented:
Why would rackspace block that test?  What about the outbound & inbound tests did they work?

So you're saying you can't send to ANY of your hosted domains from your own onsite exchange 2013 server?

But,  anyone outside your internal domain can send and receive from the hosted domains just fine?
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purpleoakAuthor Commented:
Not sure why they'd block it. I'll start a support conversation with them shortly.
But to answer your other questions, yes that is the case. The only address I can send to is the domain that is set to default - outboundemail.co.uk
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purpleoakAuthor Commented:
Did the inbound and outbound smtp test and it passed, moaned about the lack of SPF setup but otherwise got green ticks
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purpleoakAuthor Commented:
I fixed he issue myself within our rack space control panel.

Had the domains set as an alias of another domain changing it so that the new domains are not just aliases fixed the issue
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purpleoakAuthor Commented:
fixed the problem we were originally having
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