Hi all. I've been managing Exchange for ten years (but I'm not speciailzed nor an expert) and I've never run across a problem like this. Our Exchange 2003 SP2 server is sending duplicates of certain types of messages to external recipients. We're not sure when this started and our tests were confusing at first due to the fact that some mail providers, notably Gmail, very intelligently detect and drop the duplicates. Hotmail/Live doesn't nor does Charter, which is what I am using to test. Scenarios where it sends two of every message, every time: Whenever sending from mobile/smartphone users using EAS (to recipients outside of our organization, but not to recipients inside) When we send from a PHP Mailer app on our intranet (to recipients outside of our organization, but not to recipients inside) Scenarios where it sends only one of every message: When the recipient mailbox is on our server When sending using Outlook (Windows) When sending using Outlook Web Access When sending using a command line email tool such as Blat When submitting emails directly via telnet to port 25 Third party products installed are: Vipre Email Security for Exchange (recently switched to this from McAfee Groupshield) DisclaimIt (policy-based html and/or plain text disclaimers, installed for several years) Shavlik Netchk Protect (for Microsoft and third party software security patches, installed in conjunction with Vipre) We also forward outbound SMTP messages to an encryption appliance, but logs prove it is receiving duplicates from Exchange and the problem remains even if we stop forwarding through the appliance temporarily. I've exhausted all of my own troubleshooting ideas, so any ideas or leads from anyone reading this will be most appreciated!

When you look at the Internet headers of one of the duplicate messages do they show the same or a different message ID? That piece of information is a tip as to whether the message was sent twice or duplicated in transit. -- Ed Crowley MVP "There are seldom good technological solutions to behavioral problems." . "chager" wrote in message news:abc3aba3-258b-4492-a4c0-d8f6aef52a85... Hi all. I've been managing Exchange for ten years (but I'm not speciailzed nor an expert) and I've never run across a problem like this. Our Exchange 2003 SP2 server is sending duplicates of certain types of messages to external recipients. We're not sure when this started and our tests were confusing at first due to the fact that some mail providers, notably Gmail, very intelligently detect and drop the duplicates. Hotmail/Live doesn't nor does Charter, which is what I am using to test. Scenarios where it sends two of every message, every time: Whenever sending from mobile/smartphone users using EAS (to recipients outside of our organization, but not to recipients inside) When we send from a PHP Mailer app on our intranet (to recipients outside of our organization, but not to recipients inside) Scenarios where it sends only one of every message: When the recipient mailbox is on our server When sending using Outlook (Windows) When sending using Outlook Web Access When sending using a command line email tool such as Blat When submitting emails directly via telnet to port 25 Third party products installed are: Vipre Email Security for Exchange (recently switched to this from McAfee Groupshield) DisclaimIt (policy-based html and/or plain text disclaimers, installed for several years) Shavlik Netchk Protect (for Microsoft and third party software security patches, installed in conjunction with Vipre) We also forward outbound SMTP messages to an encryption appliance, but logs prove it is receiving duplicates from Exchange and the problem remains even if we stop forwarding through the appliance temporarily. I've exhausted all of my own troubleshooting ideas, so any ideas or leads from anyone reading this will be most appreciated! Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Thanks for responding. The headers show identical message ID's. I'll paste examples below. The SMTP log on the server actually shows two complete conversations between our server and the remote server as well. In one case there was a RSET between the two and in the other case there was a QUIT at the end of each. HEADERS: Message ID's from Exchange server to ISP: Received: from mail.xxx.us ([x.x.x.x]) by imp08 with charter.net id HUJ01e06h3gnQtS04UJ1RN; Fri, 14 May 2010 12:18:01 -0400 Received: from mail.xxx.us ([x.x.x.x]) by imp08 with charter.net id HUJ01e06h3gnQtS04UJ1RN; Fri, 14 May 2010 12:18:01 -0400 Message ID's from my Droid to Exchange: Message-ID: <000801caf381$21eddf47$1c01640a$30001@xxx.us> X-Mailer: TouchDown Message-ID: <000801caf381$21eddf47$1c01640a$30001@xxx.us> X-Mailer: TouchDown

I haven't solved this issue yet, but I did narrow it down to one of the third party products that we have. The "DisclaimIt" disclaimer software. I temporarily disabled it and the problem went away. I'm going to pursue the issue with them at this point. I'm posting this merely for the benefit of future googlers.

Good. I was going to suggest disabling or removing those as well. -- Ed Crowley MVP "There are seldom good technological solutions to behavioral problems." . "chager" wrote in message news:feb20f19-17ee-4f88-ad1f-8ee424ab0c91... I haven't solved this issue yet, but I did narrow it down to one of the third party products that we have. The "DisclaimIt" disclaimer software. I temporarily disabled it and the problem went away. I'm going to pursue the issue with them at this point. I'm posting this merely for the benefit of future googlers.Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

charger, why not to try a proven software? I've been using CodeTwo Exchange Sync for one year and never experienced problems like you did. And if you need to manage your e-mail signatures and disclaimers, you can also use CodeTwo Exchange Rule s. I didn't use this one, but I've heard some good opinions about it. Anyway, you can try it for free: Free CodeTwo Download . Maybe it'll be a help for you.