Emails going into Drafts instead of Sent folder

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Senior Member
Outlook version
Outlook 2016 32 bit
Email Account
This happened on the same IMAP account that I referred to in my Carbonite thread yesterday, but it seemed better to make a new thread for this question.
He sent some emails a year ago and when he needed to refer to them today, they are not in his Sent folder. But I was able to find them in the Drafts folder.
I confirmed that they were indeed sent because went I looked into his Inbox for the same day, I found a reply he received from the addressee, that also contained, if you scrolled down in the message, the content of the original email, which is the one I found in Drafts instead of the Sent box. Any ideas how this may have happened?
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That may explain the draft still being there, although he is not the kind of guy to intentionally create a draft.

It is pretty clear it is not in the Sent folder. The email he is looking for was sent in December of 2017. The Sent folder only shows 6 emails sent for the whole year of 2017. When in fact there should be hundreds, like there are for 2018.
There are two people that have this IMAP account on their computers, the woman who owns the business, and the guy who is the assistant. He is the one who sent the email. But neither of them would ever delete any emails from any box. In fact the owner has 124,000 emails in the Inbox on her other account, which is pop3. I am trying to get her to let me archive them.
We have been able to more or less reconstruct the email trail by using the reply we found in the Inbox, and the draft I spoke about. So I guess this will just remain a mystery.

Thanks again for all your help.
he is not the kind of guy to intentionally create a draft.
Outlook does it every 3 min unless he changed the option.

Since its imap, he needs to log into web mail and see if the missing items are on the server. Also, in File, Account settings - open the dialog and double click on the account - is it set to sync all?
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