Good Day ,, Recently Ive deployed Exchange 2007 server, everything is working fine, I can send/receive external email except Gmail !! I cant send to any gmail account, but I can receive from gmail, while I can send and receive from any other external email like hotmail, yahoo etc. After sometime of trying to send from OWA or Outlook to gmail, I get the following: ============ Delivery is delayed to these recipients or distribution lists: anyemail@gmail.com Subject: test This message has not yet been delivered. Microsoft Exchange will continue to try delivering the message on your behalf. ============ The next day I get the following: ============ Delivery has failed to these recipients or distribution lists: mynameMicrosoft Exchange has been trying to deliver this message without success and has stopped trying. Please try sending this message again, or provide the following diagnostic text to your system administrator. Sent by Microsoft Exchange Server 2007 Diagnostic information for administrators: Generating server: myserver.COM myemail@gmail.com#550 4.4.7 QUEUE.Expired; message expired ## Original message headers:Received: from myserver.COM ([IP address]) by myserver.com ([IP address]) with mapi; Thu, 4 Dec 2008 10:01:58 +0300From: test test@mydomain.comTo: myname <myemail@gmail.com>Date: Thu, 4 Dec 2008 10:01:50 +0300Subject: RE: testThread-Topic: testThread-Index: AclV2f/LFuOukfHKRpK5wCwlecxkPAABC6yUMessage-ID: <89AA21548C5C9A4FB4BB194CAC09F8A502DFCA85CC@myserver.com>References: <ccaf6cbf0812032232g516d058g1e16d1f964fc66f9@mail.gmail.com>In-Reply-To: <ccaf6cbf0812032232g516d058g1e16d1f964fc66f9@mail.gmail.com>Accept-Language: en-USContent-Language: en-USX-MS-Has-Attach:X-MS-TNEF-Correlator:acceptlanguage: en-USContent-Type: multipart/alternative; boundary="_000_89AA21548C5C9A4FB4BB194CAC09F8A502DFCA85CCmyservercom_"MIME-Version: 1.0 ============ Any idea why is this problem and what is the solution ?? Best Regards ,,Alibah

Hi Alibah, Can you test the SMTP communication manually with Telnet to the MX record of Gmail from your server? Get the MX record of Gmail with below article. How to Use Nslookup to Verify MX record configuration http://technet.microsoft.com/en-us/library/aa998082(EXCHG.65).aspx Test the SMTP communication to MX record of gmail as per below article. How to Use Telnet to Test SMTP Communication http://technet.microsoft.com/en-us/library/aa995718(EXCHG.65).aspx You may need to verify your DNS configuration of Gmail MX records for external looksups..

Hi, If you are able to get the correct MX record of Gmail and able to telnet to the Gmail mail server successfully from your Exchange Server. Please enable protocal log on the send connector and also check the Queue Viewer when the message stuck in your Exchange Server for last error. Mike

Thanks Amin and Mike .. I was on leave and I'll be trying this soon, by the way, messages sent to gmail will stuck in the queue till they expire.Regards ...

Alibah, Were you ever able to fix this issue? We have several clients who are having this same issue with their servers and are unable to send to us.