Outlook is sending multiple copies of an email

I’m having a problem with Outlook sending multiple copies of some emails – usually those with attachments.

It doesn’t happen with every email with attachments, just occasionally. It will send it 20-30 times but keeps the email in my Outbox saying that it hasn’t been sent (although sometimes it says it’s been sent but stays in the Outbox).

How can I solve this and make sure Outlook only sends out one copy again?