Hello. I am experiencing a situation that is quite perplexing, and I have not had much luck searching for answers. I am curious to know if any other admins have run into this in the past.Situation:Old messages (ranging from 2 months to 4 years) are being processed for the first time by our mail server. 2 separate accounts have reported old mail being sent with no interaction from the customer.Mail logs show that the message was sent on the day and time reported (today at 8:23am for example), but the message shows up in the Sent Items folder with a send date in the past (4/23/2004 at 2:32pm for example).Troubleshooting Steps:I have restored the mailboxes to a .pst file and found that the Outbox folder is empty.Checked server mail queues and confirmed oldest message in any queue is from today.Confirmed that the outgoing messages were not present in the restored Sent Items folder, and that a single copy of the sent item is present in live data.My thoughts:I was assuming that these messages were stuck in the Outbox, but the mailbox restore I did seems to disprove that theory. The customers are using a combination of OWA and Outlook 2007 (previously Outlook 2003), so there is no possibility of a 3rd party application (Eudora, Thunrderbird, etc...) incompatibility. I have not seen this problem before recently, no major changes to the system have been made...only standard Windows Updates and SP2 have been applied. There are no other standing problems that I am aware of with the system, it shown no signs of being anything other than functional and healthy.Has anyone else come across this type of a situation? I realize there must be some stone I am leaving unturned, but I am not sure what it might be.Thanks in advance,Chris P.S. MODS - If this is not the appropriate forum, please let me know or move.

HOw about a/v or spam filtering systems? Sounds like you've covered your exchange bases, time to start looking 3rd party :-)

good point knightly, i forgot to outline the 3rd party apps we have running. we are doing xbl via spamhaus, and are only using IMF as our anti-spam...neither of which are monitoring outgoing mail. AV is scanmail, and is the current version. i don't think we would have an issue with outgoing mail processed by scanmail, but the times involved don't match any scheduled processes...and it has been updated several times since 2004. I just don'tknow where else to go from here...and it seems like nobody has run into this before. Thanks for the response. Chris

Hi Chris, Have you checked the SMTP (servername-{guid}) mailbox? SMTP (servername-{guid}) mailbox is used by the mail transport of Exchange 200x as a temporary holding place for various messages as they pass through the system. When a message is processed by Exchange transport, the message remains in one place while passing through the various phases and memory based queues. If the message originates from the SMTP protocol (another Exchange 200x server or the Internet), then as the message comes in, it is written via the NTFS store driver to the mailroot/queue folder while going through categorization & advanced queuing. If the message originates from anywhere else -- MAPI client, OWA, or the MTA, then the message remains in the store during the same process, in the SMTP mailbox accessible to transport via the Exchange store driver using IFS. For more information: http://support.microsoft.com/kb/906557/en-us http://blogs.technet.com/evand/archive/2004/12/27/332752.aspx Mike

Does the recepient and sender are from the same exchange server? Does the messages were resent or they stalled in the transport process? It seems that we both have similar problems. I too have Outlook 2007 and OWA as exchange client. Here's a link to the description of my problem. http://forums.microsoft.com/TechNet/ShowPost.aspx?PostID=3328779&SiteID=17

I have had some messages that were internal, some that were external. I am fairly certain that the messages were stalled and not resent, as a restore of the sender's email account showed that the "3 year old message" was not in her sent items folder at the time of the restore, but was in live data. Now this in itself is not proof, except that this user has several thousand messages in her sent items folder, and many are older than 3 years. It appears to me that this user does not manager her sent items so had it been sent previously, it still wold have been in her sent items folder. It does sound like we are experiencing similar issues. I am going to try looking at the SMTP mailboxes as described in the previous post and will post my results. Chris

Hi Chris, I would just like to know whether the information I provided is helpful. Mike