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With a SBS 2011 box (Exchange 2010) there is a user complaining the mail he sent was not received.

He has used delayed send and the items were in the outbox on their Outlook client - they also show in the sent items as sent OK.

Could someone please advise where logs can be found showing the low level status of the delivery of these messages?

How can i tally up the sent item email with the item in the log?

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You need to enable logging for the SMTP connector first, if not done so already. (Setting NONE to VERBOSE). The location of the logs, by default would be at C:\Program Files\Microsoft\Exchange Server\V14\TransportRoles\Logs\ProtocolLog\SmtpSend for more info, take a look at the following article.

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    To add, often with remote receivers using STMP gateways or spam filters, it is necessary to reach out to the remote party. For instance, if a log shows "delivered" it may be necessary to find out from the remote party that while their SMTP gateway took the email it then parsed it and possibly quarantined it as spam. This would be something that only the receiving party would be able to answer.
    – TheCleaner
    Sep 11, 2013 at 15:08

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