Hi,
We have heard of issues with Outlook and it's folder handling before, unfortunately in our experience it is not the most robust email client and has it's share of bugs. I would ensure when sending to multiple recipients it is formatting the "To" field correctly, if necessary manually entering addresses instead of using the address book.
You should also ensure the IMAP folders are correctly defined, though if this is only intermittent it should not be the cause.
If switching email software is a possibility I would recommend as a better maintained and updated free alternative.
Regards,
Darryl
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