This is something I just noticed recently.
I have Office 2016, 32-bit installed on my laptop. If I ‘share’ a Word document as an attachment in an email from the Word program itself (i.e., in Word, ‘File-Share-Email-Send as Attachment), Outlook will open a new email window and stash a copy in the Outbox for sending (as per normal). However, it will not move a copy to the Sent Items folder for some reason. (It works fine for any email sent from Outlook itself.)
This is a problem, since I don’t have any record of the email being sent. One would think that since the email is being sent through Outlook (even if generated from Word), a copy would go into the Sent Items folder.
Any ideas on how to resolve this problem?