Office 365 - Email routing to on premise

Hi experts!

We have recently begun a migration to office365 from Exchange 2003.
We have started a staged migration and moved two users from on-premise to the online exchange.

I have configured DirSync and all is working with that and I have migrated the two users mailboxes over to Outlook online using Outlook Anywhere endpoint and all is ok here.

The issue we have now is that the two users who have been migrated can send email externally and users on-premise can send email to them however the two users cannot send emails to the users on premise.

After some research I wondered if:

We need to setup a server runing exchange 2007 which allows routing back to exchange 2003
or
I can setup a form of routing within online exchange to send the emails back to on-premise for delivery

We have no other users migrated over, although they are ready to be moved.

The error the two migrated users receive can be different for different recipients. It is either:

Remote Server returned '550 5.1.1 RESOLVER.ADR.RecipNotFound; Recipient not found by SMTP address lookup'
or
Remote Server returned '< #5.2.1>'

I have looked at other posts on here and I have seen the use of the NK2Edit application to remove X500 address as it will be using the legacy exchange information but this has not resolved the issue.

Any help would be gratefully received.

Shaun
Shaun HallAsked:
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Vasil Michev (MVP)Connect With a Mentor Commented:
Which server is generating the NDR, Exchange Online or your on-prem? Where is the MX pointing at, on-prem I assume? Have you set up the domain intent as "Internal relay" in Exchange Online? Post the sanitized NDR if possible
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Shaun HallAuthor Commented:
Hi Vasil,

the MX is still pointing at on-prem. The NDR seems to be the same now so we are not getting the < #5.2.1> error.

[b]Remote Server returned '550 5.1.1 RESOLVER.ADR.RecipNotFound; Recipient not found by SMTP address lookup'[/b]

Generating server: AM3PR05MB386.eurprd05.prod.outlook.com
#########@#########.co.uk
Remote Server returned '550 5.1.1 RESOLVER.ADR.RecipNotFound; Recipient not found by SMTP address lookup'


Diagnostic information for administrators:
Generating server: AM3PR05MB386.eurprd05.prod.outlook.com
#########@#########.co.uk
Remote Server returned '550 5.1.1 RESOLVER.ADR.RecipNotFound; Recipient not found by SMTP address lookup'
Original message headers:
Received: from AM3PR05MB388.eurprd05.prod.outlook.com (10.242.247.27) by
 AM3PR05MB386.eurprd05.prod.outlook.com (10.242.247.17) with Microsoft SMTP
 Server (TLS) id 15.1.59.20; Fri, 16 Jan 2015 11:45:31 +0000
Received: from AM3PR05MB388.eurprd05.prod.outlook.com ([10.242.247.27]) by
 AM3PR05MB388.eurprd05.prod.outlook.com ([10.242.247.27]) with mapi id
 15.01.0059.007; Fri, 16 Jan 2015 11:45:31 +0000
Content-Type: application/ms-tnef; name="winmail.dat"
Content-Transfer-Encoding: binary
From: ######### <#########@#########.co.uk>
To: "#########@#########.co.uk" <#########@#########.co.uk>
Subject: test
Thread-Topic: test
Thread-Index: AdAxgcBd1QeErIpdRP6M0CapDTcqwg==
Date: Fri, 16 Jan 2015 11:45:30 +0000
Message-ID: <AM3PR05MB388B941EC7A4656939FC424DA4F0@AM3PR05MB388.eurprd05.prod.outlook.com>
Accept-Language: en-GB, en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator: <AM3PR05MB388B941EC7A4656939FC424DA4F0@AM3PR05MB388.eurprd05.prod.outlook.com>
MIME-Version: 1.0
X-Originating-IP: [81.145.159.82]
Return-Path: #########@#########.co.uk
Authentication-Results: #########.co.uk; dkim=none (message not signed)
 header.d=none;#########.co.uk; dmarc=none action=none
 header.from=#########.co.uk;
X-DmarcAction-Test: None
X-Microsoft-Antispam: UriScan:;
X-Microsoft-Antispam: BCL:0;PCL:0;RULEID:(3005004);SRVR:AM3PR05MB386;

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The on-prem domain is setup in exchange as an Internal Relay

Shaun
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Shaun HallAuthor Commented:
I removed all of the settings I had setup recently and waiting a few hours before re-adding only the relay. This now works as expected.

Thanks for your help.
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