We recently moved our servers to a Data Center. Before we had our Exchange server set up with an external IP sddress. Now we have moved to a Data Center and Exchange is behind a Cisco router.We have our email going to Reflexions spam filter so the only MX record in Exchange is pointing to Reflexions. They filter all incoming email then send it to us. Since the move,we cannot send outbound email to external email addresses, and external email is not coming through the spam filter. It is coming straight to the server. I get this message when I attempt to send out external email. Any help with this will be greatly appreciated. Delivery has failed to these recipients or distribution lists: user@yahoo.comAn error occurred while trying to deliver this message to this recipient e-mail address. Microsoft Exchange will not try to redeliver this message for you. Please try resending this message, or provide the following diagnostic text to your system administrator. The following organization rejected your message: asp-6.reflexion.net. Sent by Microsoft Exchange Server 2007 Diagnostic information for administrators: Generating server: Exchange.domain.com user@yahoo.comasp-X.reflexion.net #553 sorry, that domain isn't in my list of allowed rcpthosts; no valid cert for gatewaying (#5.7.1) ## Original message headers: Received: from Exchange.domain.com ([fe80::1]) by Exchange.domain.com ([fe80::1%1]) with mapi; Mon, 14 Sep 2009 09:07:57 -0400 From: User <user@domain.com> To: "user@yahoo.com" <user@yahoo.com> Date: Mon, 14 Sep 2009 09:07:54 -0400 Subject: Monday Test Thread-Topic: Monday Test Thread-Index: AQHKNTxen3pyayjkt0iGWdKrE6k2hg== Message-ID: <5CF82F642F3A364E9016B8DB413B6D24CA40BEC411@MSPX12.mspx.com> Accept-Language: en-US Content-Language: en-US X-MS-Has-Attach: X-MS-TNEF-Correlator: acceptlanguage: en-US Content-Type: text/plain; charset="iso-8859-1" Content-Transfer-Encoding: quoted-printable MIME-Version: 1.0

Hi,"asp-6.reflexion.net." is this the name of the External send connector cretaed on Exchange 2007 or the Name of the smart host server were you are sending the mails for outbound spam filter than to internet.Remove the smarthost from the external send connector and try sending mails again.. (if not planning to scan Outbound mails)Craetion of Send Connector in Exchange 2007http://www.petri.co.il/configuring-exchange-2007-send-external-email.htmAs mentioned External mails are directly comming and hitting Exchange 2007 instead of Reflexions, that mean on your Cisco router the Public IP of MX record is directly natted to Exchange 2007 Private IP, just cross check the configuration of Cisco router, if any mistake change the rule and point it to reflections and in reflections allow traffic from the Routers Internal IP. Similarly In the reflections spam box create a rule to send the mails to Exchange 2007 internal IP after scanning inbound mails.Also on the Exchange 2007 create a cstom receive connector by adding the reflections box IP, so that exchange 2007 accepts mails from the reflections IP.Creation of Custom receiveconnectors..http://technet.microsoft.com/en-us/library/bb124327.aspxhttp://www.msexchange.org/articles_tutorials/exchange-server-2007/management-administration/managing-receive-connectors-part1.html

Issue with Cisco PIX explained here. http://www.tech-archive.net/Archive/Exchange/microsoft.public.exchange.admin/2006-12/msg02466.html Do you have PIX? Is your send connector using your external spam filtering company as smart host? If your emails are coming straight, check your MX record to see whether it is pointing to your external company. Rajith.Rajith Enchiparambil | http://www.howexchangeworks.com |

Yes "asp6.reflexion.net" is the name of the smarthost server. I removed thesmart host. When I try to send an external email I don't get any error, but the email never gets to the destination. I will try your suggestions and hope for the best. Thanks.

Also use the built in Exchange 2007 Message Tracking feature to troubleshoot, any issue post us.

Hi,From the information, it seems that is the smart host (Reflexions) issue, you can try the RockSlow's suggestion to send the email without smart host. However, you should ensure the DNS is available can resolve the external email address.ThanksAllen