Mail created with "Send to Mail Recipient" disappear and are not sent

I have a small setup with a SBS 2011 server (Exchange 2010) 10 users with Windows 8.1 and Outlook 2013.
One user is trying to send mails with attachments to his college´s
but they are never send, are not shown in sent items and can not be found on the server.
The user right click on a PDF file and press "Send to Mail Recipient" Outlook opens his mail is entered into the receiver (internal receiver) and press send. The mail do not show up and as mentioned even in sent items.
I then try to do the same but send through the address book in Outlook / Exchange and these messages appears as they should.
One week later, the disappeared mails suddenly appears in the college’s mailboxes and it turns out there are some mails to external addresses as well, which were not sent until a week. All messages are now in sent mail but they have not
appeared anywhere else before.
I did some tests with the "send to" function which also had the mails disappearing - those mails has not turned up until now. (a week ago)
Now the user (AND all colleagues) are very nervous that something is wrong with their system and the mail does not arrive.
It is only 1 user this has affected but he is responsible for the majority of sales in this company and they are very afraid that they are not responding correctly to large customers.
Is there anyone who can help with debugging in such a case?
I have tried repairing Outlook, started in safe mode, checked the mail server for hanging mails but nothing shows any errors.
Thanks in advance.
Michael Grøn
Michael Gron

Hi,
Have the user logon OWA and send the attachment, will this issue persist?
Please also confirm if the issue exists when inserting an attachment when composing a new email isntead of using the "Send to Mail Recipient" function.
Since only one user has been affected, use MFCMAPI to find if the message is stuck in the user's mailbox:
https://mfcmapi.codeplex.com/releases/view/118446
Please Note: Since the web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.
Thanks,
Melon Chen
Forum Support
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