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Invalid email addresses

We have a number of out of office email replies stuck in a loop between an x400 and local delivery queue.  The original email is being delivered with a valid email address from our email host to our exchange servers, but in the header of the email the 'From' address is invalid,  ie the . or underscore is being removed from the body of the email address leaving blanks in the address therefore when the out of office reply is sent, the system only sees the part of the email address before the space and thinks its an internal address turning the address into xxxxx@local (x's being the first part of the original email address) and because this is not a valid local email address the out of office reply gets caught in a loop betweent the queues  with no expiry date or NDR notification. This only happens to a very small number of incoming emails and only happens with out of office replies.  Microsoft have recommonded that we stop the McAfee Groupshield (ver 7.0.716) service on our Exchange servers, however I would like to know if it is possible to track the original email to see at which point and why the valid email address in the Return-path field in the header becomes an invalid address in the From: field.
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Barnardos_2LS
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Barnardos_2LS
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Antonio VargasMicrosoft Senior Cloud ConsultantCommented:
Is the out of office e-mail generated inside or outside your organization? It's very likely to be Mcafee the originator of this problem changing the e-mail from field, but it's also important to track the e-mail from the source.
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Barnardos_2LSAuthor Commented:
Hi, the out of office reply is generated inside the organisation, using the standard Outlook 2003 client. Its just odd that its only happening to a very small number of addresses, although saying that it may be happening more often but only being highlighted by the OOF messages because they are sending an autoreply and therefore this highlights the invalid address. Ive tracked some of the originating emails from the source and everything in the header of the originating emails seem to be ok except for the 'From' address.  There is nothing in the Groupshiled logs to indicate it has done anything to these emails except the standard scan when originally recieved.
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Antonio VargasMicrosoft Senior Cloud ConsultantCommented:
And out of office messages sent to users on the same exchange server also have those problems?
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Barnardos_2LSAuthor Commented:
No, it appears from the emails that I have been able to check, its only Out of Office messages being sent to external email adresses
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Antonio VargasMicrosoft Senior Cloud ConsultantCommented:
ok so if the problem is only to external e-mail addresses than i think that is safe to conclude that the problem is not on the source but somewere between your org and the outside world. Are the mails sent to outside the org beeing relay on anything or is the outgoing mail going directly from exchange to the Internet?
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Barnardos_2LSAuthor Commented:
We have a secure tls connection to a 3rd party host who scan all our incoming/outgoing emails. I have  used their track and trace facility on their portal to check the email coming in and the email address is valid at this stage, it appears to be only when it reaches the recipient that the 'From' address is invalid
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Barnardos_2LSAuthor Commented:
As part of the problem I have reviewed the exchange transaction logs and have a question around which email address the out of office rule should reply to. In the following example there are 2 email addresses showing in the header of the incoming email, the 'Reply to' address which is a valid email address say for example mickeymouse@exchange.co.uk and a 'from' address which is a friendly name i.e Mickey Mouse. Looking at the SMTP event IDs the friendly name (From) 'Mickey Mouse' appears against all the smtp event ids for the delivery of the email except against event ID 1028 which uses the 'Reply to' address mickeymouse@exchange.co.uk as the senders address. The out of office rule is trying to reply to the friendly name which is not a valid email address and therefor the system tries to create it as a valid email address turning it in to mickey@local. Is it correct fof the OutofOffice reply to try and reply to the friendly name 'From' or should it be replying to the Reply to address which includes a valid email address?
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Antonio VargasMicrosoft Senior Cloud ConsultantCommented:
The out of office should reply to the e-mail address and not to the friendly name, because i assume the user is not on your internal infrastructure. So what you can try as a test is create a contact with that friendly name and with the e-mail address to see if it solves the problem. Not to apply this as a solution but only to be sure that the problem is generated right on the start for out of office misfunctioning.
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Barnardos_2LSAuthor Commented:
The issue was due to 3rd party software causing a small number of OOO replies being caught in a loop. The resolution was to add an additional rule to exclude footers being applied to any OOO autoreplies.
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Barnardos_2LSAuthor Commented:
Self resolved.
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