Sending, receiving, and organizing email in Outlook.com
Hi, I'm John! I will help you with this.
First try sending a simple test email with no attachment and no links to another email address, if you have one. Then check if it appears in Sent Items.
Also, to help narrow down the issue:
- Does this happen with all recipients, or only one person/company?
- Do you receive any bounce-back or delivery failed message?
- Are you sending attachments, links, or repeated similar messages?
Also, please ask the recipient to check with their email provider or IT team if your address is being blocked on their side. Sometimes Outlook shows the message as sent, but the receiving server rejects or filters it before it reaches Junk/Spam.