Using Classic Outlook on Windows for personal email, calendar, and contact management
Welcome Mark Fishburn,
Thanks for reaching out to Microsoft Q&A Forum. I understand that you have turned on sending from aliases in the Exchange admin center and the alias receives mail correctly. However, messages you send from the alias in Outlook on the web and Outlook for Windows still arrive from your main email address.
To narrow this down, could you please confirm:
- In Outlook for Windows, under File > Account Settings > Account Settings, does the Type column show Microsoft Exchange, or IMAP/POP?
- In your Sent Items folder, does the sent copy show the alias or the main address in the From field?
In the meantime, you can try these steps:
1, Confirm the mailbox is hosted in Microsoft 365
- Sending from aliases only works for mailboxes hosted in Exchange Online.
- If Outlook connects to the GoDaddy cPanel mailbox through IMAP or POP, the message is sent through the cPanel server, which can replace the From address. In that case, use the mailbox connected as a Microsoft 365 or Exchange account.
2, Check that your domain is allowed to send
- Connect to Exchange Online PowerShell and run:
Get-AcceptedDomain | Format-List Name,SendingFromDomainDisabled - If mysite.com shows True, run:
Set-AcceptedDomain -Identity mysite.com -SendingFromDomainDisabled $false
3, Look for rules or connectors that change the sender
- In the Exchange admin center, go to Mail flow > Rules and Mail flow > Connectors.
- Look for any rule or outbound connector that changes the sender address or sends outgoing mail through GoDaddy or another filtering service. Disable it temporarily and test again.
4, Run a message trace on the alias
- In the Exchange admin center, go to Mail flow > Message trace.
- Search using the alias address as the sender, not the main address. This shows whether the message left Microsoft 365 with the alias.
5, Update Outlook for Windows and pick the alias from the From field
- Go to File > Office Account > Update Options > Update Now, then restart Outlook.
- In a new message, select From > Other email address, type the full alias address, and send a test message to an external address.
Looking forward to your update.