Sending, receiving, and organizing email in Outlook.com
If the message is now in Sent Items, that is usually a good sign, but moving the conversation from Deleted Items to Sent Items afterward does not by itself prove the email was successfully sent. Outlook normally places sent messages in Sent Items, while unsent messages may remain in the Outbox.
To check:
- Look in Outbox for a copy of the message. If it's there, it likely has not been sent yet.
- Check whether you received a delivery failure (NDR) message. If not, the message may have been delivered successfully.
- If possible, ask the recipient whether they received the email (and to check Junk/Spam if necessary).
Also, if messages in that conversation are being moved to Deleted Items, check whether the conversation was accidentally set to Ignore, as Outlook can automatically move messages from ignored conversations to Deleted Items.