Only happens to this one domain. A series of emails and replies sent back and forth. Some of the email addresses will have extra or shifted characters. foobar@foobarinc.com foo@.bar.foobarinc.com or foo.bar.foo@barinc.com or foo.bar@forbar.inc.com So of course you get bounced message Seems to be random the only common are the two domains. XP SP2 Outlook 2003 Exchange 2003

I have never seen Exchange Server do this. The e-mail addresses that are stamped on the messages are pulled from the Active Directory, so you can probably take the client components out of the equation unless you are using POP3 clients. Are you? If so, then through the clients back in to the equation since the user configures their SMTP address on a POP3 or IMAP4 client. Does the e-mail go through any additional gateways such as a message hygiene system or a Unix system that might re-write the SMTP addresses?

Clarify: The SMTP address of some mails became invalid / corrupted only when one domain [domain a] send mails to another domain [domain b], right? Please do a test [Domain c: Completed normal domain, both send and receive is ok]: 1. Send mail from domain a to domain c 2. Send mail from domain b to domain c 3. Send mail from domain c to domain a and b 4. Check the issue [To and From field] and post the results Collect info: 1. Can you check affected mails Message History in Message Tracking Center and post? 2. Also, provide related SMTP protocol log file, issue screenshot. You can post here or send to me Notes: [Microsoft Services File Transfer Website, Password: zP@kpjIc7cd]

I am having a similar problem, but it is not confined to two domains. It does seem to happen more often withcertain domains though. I have gotten copies of emails from the affected parties and been able to narrow it down some. User A (on my domain) sends an email to User B (outside domain), there are other recipients (ie. userc@somedomain.com). These other users can be on the same domain as A or B. When user B replies, not all addressees get the email because one or more of the addresses have become corrupt. This is because a space or a dot was inserted into the email address in the header. I have gotten copies of the emails sent to me (as attachments on a new email) and I can see where it becomes corrupt. User A sends email to userb@somecompany.com and userc@someothercompany.com. When userb gets the email, userc's email address shows up as something like "us erc@someothercompany.com" or "userc@som.eothercompany.com." This is causing a lot of user frustration, and I have made changes to our system to reduce the number of touches made by systems on my end to narrow it down. Mail server - Server 2003, Exchange 2003, Symantec Endpoint Protection, GFI MailEssentials and MailSecurity (allwith latest service pack, updates, and patches). Client - Windows XP SP 2 and 3, Outlook 2007, Symantec Endpoiint Protection Mail system on recieving end - Unknown

We have had a very similar problem and as yet have been unable to resolve - would be very interested in any suggestions. In our case we are using Exchange 2003 and most users have GoldMine CRM which uses POP3 and SMTP to access their mailboxes and send emails. Examining problem emails in an email conversation we can see that initially the recipient is seeing email addresses like: "user@ourcompany.com" <user@ourcompany.com> but as emails are exchanged we it becomes apparent that on the recipient's machine the reply to address has become corrupted to something like this in the From header: user@ [mailto:ourcompany.com user@ourcompany.com] and when they reply this becomes: user@ The facts as we have them are: As far as we're aware this is affecting only 2 users out of around 50 but the problem affects emails to a variety of customers (no information on their systems - but Exchange 2003 is in use in at least one case). The problem appears to be very recent - perhaps in the last 3 months and we are not able to identify any changes in our systems that would affect this. Our mail goes out from Exchange then through a gateway (exim) - we can see that the email address reported at the gateway appears to be correct (but can't be sure at this time that this is picked up from the headers in the email). We are running Exchange 2003 and in the last week have moved to a new installation on a new server, moving all our mailboxes - the problem is still occurring. We had Symantec installed on the old server but not on the server we have just installed so don't think this is a factor The affected users are using GoldMine and NOT Outlook Any ideas???? OK - I finally have a clearer idea of the problem that affects us and a workaround... We are using GoldMine as a CRM and email client. The problem occurs under a specific set of circumstances when GoldMine uses the address that the customer sent the email to as the From address in any response. If the customer sends the email with a To address of the form "someone@somewhere.com" <someone@somewhere.com> then GoldMine seems to strip the quotes from the header when reading it and when constructing the reply will offer someone@somewhere.com <someone@somewhere.com> (no quotes) as one of the options for the From address with the users usual email address (e.g. Some One <someone@somewhere.com> ) as the other option. However the From address that is constructed into the email body itself is corrupted and of the form: "someone@" <somewhere.com someone@somewhere.com> - when a customer replies their client often uses someone@ as the email address, which then bounces! Fortunately we run Exim on our gateway and I have been able to knock up a simple filter to address the problem. Basically it traps malformed addresses, extracts the actual email address and replaces the From header with a corrected version: ### If corrupt GoldMine From header is found: ### "someone@" <greymatter.com someone@greymatter.com> ### then extract the email address part and replace the From header. ### NOTE - change the @somewhere to your domain... if ($h_from: matches "^\".*@\".*<.* (.*@.*)>") and ($h_from: contains "@somewhere") then headers remove "From" headers add "From: $1" endif

I know this thread goes back two years but I am facing a similar problem using Exchange 2003 and Outlook 2010 I am also using Read Earth (PolicyPatrol) as a spam server. emails are user.lastname@domain.net but when the recipient replies it seems the name is changed to user.lastname@www.domain.net . This is happinining only with some sites while the others are able to reply without any problems. All users and domains are added to the PolicyPatrol white list. I looked all over the place and have no idea where the "www" is added to the reply email. I would appreciate any help in resolving this. Feel free to email me directly to gaith.abdo1@verizon.net