Messages I send from hotmail are not received

Dear FN,  

Good day! Thank you for posting to the Microsoft Q&A Forum. We are happy to assist you. 

I understand that you are having trouble with emails sent from your Hotmail account not being received by others, even though they show up in your Sent folder. I appreciate you for your detailed description and for all the troubleshooting you have already performed, as this helps narrow down the potential causes. 

Since the messages are in your Sent folder, this indicates that your Outlook for Mac client has saved them, but they may not have been successfully handed off to the Hotmail server for final delivery. This is often a sign of a server-side delivery issue or a client configuration problem. 

Here are a few steps we can try to help diagnose and resolve this: 

1. Test Sending from Outlook on the web: Please open a web browser and go to Outlook.com. Sign in to your Hotmail account and send a test email to one of the same recipients. This is the most important step, as it will tell us if the problem is with your account itself or isolated to your Outlook for Mac application. 
2. Verify your Account Settings: 
   1. In Outlook for Mac, go to Preferences > Accounts. 
   2. Select your Hotmail account and click Advanced. 
   3. Under Outgoing server (SMTP), please double-check the server name, port, and authentication settings. The recommended settings for consumer accounts are: 
      1. Server: smtp-mail.outlook.com 
      2. Port: 587 
      3. Encryption: Use SSL to connect or STARTTLS 
3. Check for Outlook Updates: Ensure you are using the latest version of Outlook for Mac. Go to Help > Check for Updates to install any pending updates that may fix known syncing or sending issues. 

Here's a helpful article that covers common sending and receiving issues for your reference: I can't send or receive messages with Outlook for Mac - Microsoft Support 

We also recommend asking your recipients to check their email filters, rules, and blocked sender lists, as messages can sometimes be routed to folders other than spam. 

Please let us know the results of these steps, especially whether the test from Outlook.com was successful. 

If the issue persists after these steps, please let us know: 

• Whether the problem occurs with all recipients or only specific ones. 
• If you’ve tried sending from another device or email client. 
• Any recent changes to your account or system. 

We look forward to your next update for further analysis. 

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