When sending a mail including Read\Delivery requests & confidentiality flag. The mail does not appear in the Sent Items folder. This is happening in the users personal mailbox and shared mailbox. Other users of the shared mailbox are not reporting an issue. Mark

hi, Do the recipient finally receive the mail? If you send some other message, such as no request/no confidentiality flag, do the messages appear in the sent items folder? All users meet it or some of them? Make sure that box save copise of the messages in the sent items folder is enabled in outlook settings. Make sure that no outlook rule is enabled. hope can help you thanks, CastinLu TechNet Community Support

Hi Castinlu, The recipients do receive the mail. It appears to only affect mail that is sent with Read\Delivery requests & confidentiality flag. Any other mail is appearing in the 'Sent Items' folder. Other users of the shared mailbox have tested and the mails are appearing in the 'Sent Items' folder. So this points to a local problem specific to the one user. Mark

hi, >>>Other users of the shared mailbox have tested and the mails are appearing in the 'Sent Items' folder. The same mail? >>It appears to only affect mail that is sent with Read\Delivery requests & confidentiality flag. Only include read request or confidentiality, the issue still occur? I don't think it is related to the request, i would like to think it is related to your flag. Try to send the mail on another PC using outlook. thanks,CastinLu TechNet Community Support

Tests confirmed. Other users not experiencing issue. Tested Read/Delivery Receipt = Mail did not appear in Sent Items Tested High/Confidential = Mail did not appear in Sent Items Tested without High/Confidential & Read/Delivery Receipt = Mail did appear in Sent Items Attempted Detect & Repair, issue still occurring.Mark

hi, If you use owa, the issue still occur? hope can help you thanks,CastinLu TechNet Community Support

Hi Castinlu, User does not use OWA Mark

hi, Try to use owa, it can help us troubleshoot your issue. we can make sure the issue is at server side or client side. hope can help you thanks,CastinLu TechNet Community Support

Ended up swapping out users PC, all working fine. Could not find any discrepancies between PC's i.e. Registry settings, Mail config etc. Mystery.... but resolved. Mark