Well it didn't sort it out the lady used the send on behalf function. I have also found out that it's not the SQL box but the client machine sending the mail.
I was receiving the following
Received: from Mar-ACC (192.168.4.90) by ServerAddress (192.168.4.2)
with Microsoft SMTP Server id 8.1.393.1; Fri, 7 May 2010 08:50:23 +0200
Date: Fri, 7 May 2010 08:50:34 +0200
From: UserName <username@domain.com>
Sender: <username@domain.com>
Reply-To: <username@domain.com>
To: <externalUser@doamin.com>
X-Mailer: Blat v2.4 w/GSS encryption, a Win32 SMTP/NNTP mailer
Message-ID: <01caedb1$Blat.v2.4$9806e164@192.168.4.2>
Subject: Invoice on account: CAT1
MIME-Version: 1.0
Content-Type: multipart/mixed;
boundary="=_BlatBoundary-Hp2jqk04HqsWzw8hW5noD"
Return-Path: username@domain.com
X-MS-Exchange-Organization-PRD: domain.com
X-MS-Exchange-Organization-SenderIdResult: None
Received-SPF: None (ServerAddress: username@domain.com does not
designate permitted sender hosts)
X-MS-Exchange-Organization-SCL: 3
X-MS-Exchange-Organization-PCL: 2
X-MS-Exchange-Organization-Antispam-Report:
DV:3.3.5705.600;SID:SenderIDStatus None;OrigIP:192.168.4.90
I then added the IP address to the receive connectors and the Anti Spam allow list and received the following
Received: from Mar-ACC (192.168.4.90) by ServerAddress (192.168.4.2)
with Microsoft SMTP Server id 8.1.393.1; Mon, 10 May 2010 09:06:08 +0200
Date: Mon, 10 May 2010 09:06:20 +0200
From: UserName <username@domain.com>
Sender: <username@domain.com>
Reply-To: <username@domain.com>
To: externalUser@doamin.com
X-Mailer: Blat v2.4 w/GSS encryption, a Win32 SMTP/NNTP mailer
Message-ID: <01caf00f$Blat.v2.4$4b29cfcc@192.168.4.2>
Subject: Statement on account: R1J
MIME-Version: 1.0
Content-Type: multipart/mixed;
boundary="=_BlatBoundary-ovnEwpgooDNDHM4WlDbuC"
Return-Path: <username@domain.com>
X-MS-Exchange-Organization-Antispam-Report: IPOnAllowList
X-MS-Exchange-Organization-SCL: -1
Which to me looks like it worked, but the mail is still not going out. Any ideas.
MCITP:EA/SA, MCSE, MCSA, MCDBA, MCTS, MCP+I, MCP