Follow this legacy reference when using the classic Outlook 2019 interface to send from an existing mailbox. Check the sending identity carefully if your Outlook profile contains both personal and business email accounts.
Outlook 2019 support ended on October 14, 2025. Use a supported email application for ongoing use. This legacy guide and video describe classic Outlook 2019, not new Outlook.
Before you start
- Confirm that the mailbox is already configured and that Outlook is connected. For an initial test, choose a recipient whose inbox you can check.
- Prepare the files you intend to send and verify the address independently when needed. Autocomplete can suggest an outdated address or another person with a similar name.
Instructions
Open a new message
In Mail, select New Email on the Home ribbon. Check the From account and choose the intended business mailbox if several accounts are available.
Add the recipients
Enter the destination in To and add Cc or Bcc recipients only when needed. Review the resolved addresses rather than just their display names.
Compose and attach
Enter a clear subject and your message. Use Insert, then Attach File for any required document, and confirm the file is the intended version.
Send once
Review the complete message and select Send. If Outlook is offline, the message may remain in the Outbox until a successful connection and send operation.
Check the result
- Check the sending account's Sent Items folder and verify receipt for a test message. A sent copy is useful evidence of submission, but not proof that it reached the recipient's Inbox.
Troubleshooting
- The message remains in the Outbox
- Inspect connection status and send/receive errors before trying again. A large attachment or incorrect SMTP credentials can prevent transmission without stopping incoming mail.
- The recipient reports the wrong sender address
- Check the From account in the saved message. Correct the account selection in a new draft; do not assume the default account matches the folder you were viewing.
Watch the video
The video may show an older interface. Use the written instructions above when screen names differ.
