Outlook email not sent and not in sent items

We've been experiencing this 'phenomenon' for several weeks. Randomly, different users believed to have sent email when no email was ever sent. In fact no trace in our Exchange logs either. Each had a random window in which any email sent just disappeared.
It never made it to sent items and never made it to our exchange server. All with no Outlook errors and appearing to functioning normally thereafter.
In one case a user had discovered an entire days worth of mail had unknowingly not been sent and was not found in the sent items folder.
These installations are on new machines, Outlook 2013 (o365) and Windows 8.1 with all updates applied. For one it happened on the first day and for others it happened a few weeks later.
Everything I find on the web seems to lead to nowhere because it can't be reproduced and once discovered, if ever discovered at all, it's too late.
Up to now we've only disabled cached mode and are waiting to see if it re-occurs but it will only be when someone actually notices it.
Anyone else seeing this?
Shawn

Hi
As per the information and details provided by you, to solve the issues with Outlook send emails, please follow these steps: -
In Outlook 2013, emails are not send may be because of the following reasons: -
A message is stuck because it has a large attachment.
You open a message or view Outlook while emails are waiting to be sent.
Wrong or changed password for the email account.
Incorrect settings, account not properly authenticated with the email server.
Outlook is set to work offline or the mail server is offline.
No email account is set as default.
Use of software that accesses Outlook data files (.pst or .ost)
Antivirus or anti-spam software is scanning your outgoing email.
Enable the Save copies of messages in the Sent Items Folder option by following the steps below for your version of outlook:
Click
File > Options.
In the
Outlook Options > Mail.
Under the
Save Messages section, enable the Save copies of messages in the Sent Items folder option.
Click
OK.
I hope this information will be helpful for you.
Thanks and regards
Shweta@G 

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