Hi I have a most curious issue, I will try to give example best I can: User A sends email with attachment (ie PDF) to external recipient 123@123.com User B sends same email with same attachment to same recipient User C sends same email with same attachment to same recipient User A sends same email but Zips the file to same recipient All users are using WinXp and OLK 2003. Recipient 123 receives User A's email but NO attachment, even when file is zipped, recipient also receives User B's email but no attachment and finally User C's email is received WITH attachment. All Users are using HTML format emails except User C, she is using Plain Text. I have tried changing the other users to plain text for the purpose of testing but I still get the same result and it is always to the same recipient. Is this issue buried inside Outlook 2003 somewhere? I say that as I cannot see how it can be related to the Exchange 2007 server we are running??? Hope someone can shed some light on this as it is driving me crazy. Kind regards Chris PS Sorry I have ended up in the wrong forum here

Hello, What is the size of the attachment? Do you have any mail security software like Scan mail,Symantec mail security? Also you can verify the Message from message tracking feature in exchang 2007. Thanks Mhussain

Hello, What is the size of the attachment? Do you have any mail security software like Scan mail,Symantec mail security? Also you can verify the Message from message tracking feature in exchang 2007. Thanks Mhussain Hi Attachment can vary in size from 20kb to 200kb We are running Symantec Endpoint Security with client installs that report to an Endpoint server on our network. Also running GFI Mail Security & Content Security on a separate Virtual SMTP server. I've traced the message through message tracking in Exchange and the message shows as delivered and the file size appears consistent. If User A/B also send same email to many recipients, all the recipients will receive the attachment except the one particular email address. Hope I haven't confused matters further there Thanks Chris

Hi, Whether the UserA and UserB could send the email with ZIP attachment to 123@123.com? Whether all the type of the attachments could not be sent to 123@123.com by UserA and UserB? And please try to disable the security software to check this issue. Thanks Allen

Hi , If in case the users A,B & C ,they are the internal users who are sending a mail with attachment , Some how the mail is getting delivered to 123@123.com without the attachment . If it is filtered by any of the antispaming software or any email security engines , then i will leave a message with the email(stating that the attachment is removed due to some policies )which is delivered to the user(123@123.com) . Is it possible for you to provide a example format of the email which 123@123.com is receiving from user A & B?Regards, G.Ganesh | Exchange Admin

It's been a while and sorry for late responses but here is where I am at with this issue: Internal user A sends email with attachment (this can be anything, pdf,xls and so on) to external recipient 123@123.com. 123@123.com receives email but attachment is missing. Internal user B follows same procedure and 123@123.com receives the email AND the attachment. As a process of elimination I removed User A mailbox thus also removing his AD profile. I then created User A mailbox with a new smtp and AD profile, then I created a new profile on another machine and created a new Outlook profile on that machine for User A. Did the same test email to external recipient 123@123.com and still the attachment is missing. I can now only assume this issue lies inside exchange and his profile or on GFI Mail Essentials/Security server. With the GFI Mail software, I would normally receive an email if any attachments are blocked and asking for approval. Really not sure where to look next, what info can I provide from the external recipients received email?

I have today now tried to send to external recipient from my email account in HTML, Plain Text and Rich Text and still this group of recipients @123.com can not see the attachment. Do you think this problem is at the recipients end?

Also Im using Outlook 2007 and user A is using Outlook 2003

Hi, Now please try to enable Transport Pipeline Tracing to record the process in order to troubleshoot it: Set-TransportServer Exchange server name -PipelineTracingSenderAddress UserA@domain.com -Pipelinetracingpath C:\Trace -PipelineTracingEnabled $True How to Enable Pipeline Tracing http://technet.microsoft.com/en-us/library/bb125018(EXCHG.80).aspx Then reproduce this issue and send the log to me Thanks Allen

This is a known problem with Outlook and its interpretation of email headers. We have seen the same behavior. Only real workaround we have found so far is to send the mail as plain text. please see http://knicksmith.blogspot.com/2007/03/exchange-2007-and-outlook-2003-where.html