URGENT HELP PLEASE Unable to send emails in Outlook

Question

When I click send, the email goes to the drafts folder. When I double click to send, the unable to send message comes up and the email remains in the drafts folder.

This is urgent as the current unsent emails are replies.

Answer 1

The problem you describe indicates that your account isn't configured properly for the outgoing server. Did you configure the account manually or allow Outlook to configure it automatically? Do you have two-factor authentication enabled on the server side?

Answer 2

Hi. I'm Brian and I'll try to help.

Who is your mail provider - that is, what follows the @ in your address? What type of account have you added in new Outlook - IMAP or Exchange?

Answer 3

None of the above worked.

Answer 4

Follow these steps in order, testing send after each step:

1. Check if Outlook is offline or disconnected
   • Look at the bottom status bar of Outlook.
   • If it shows Disconnected, Working Offline, or Trying to connect…, Outlook cannot reach the mail server.
   • Go to the Send/Receive tab on the ribbon and select Work Offline once to toggle back online.
   • Then choose Send/Receive and try sending again.
2. Confirm internet connectivity
   • Open a browser (Microsoft Edge or Google Chrome).
   • Browse to http://www.microsoft.com or http://www.bing.com.
   • If these sites do not load, fix the network connection first; Outlook will not send mail without internet access.
3. Check for large attachments
   • Open the message in Drafts.
   • If it has large attachments (typically over 20–25 MB), remove them.
   • Optionally, upload large files to OneDrive and send a link instead.
   • Save and send the message again.
4. Force a manual sync
   • In Outlook, use the Sync button on the View tab (if available) to manually sync and send messages.
   • Watch the status message at the bottom of the message list while Outlook is syncing.
5. Verify mailbox/storage is not full (if using Microsoft cloud mailbox)
   • If the mailbox storage is full, sending and receiving will fail.
   • Check mailbox storage and delete unnecessary items (especially large messages and Junk/Deleted Items), then try sending again.
6. If still failing, check for profile/add‑in issues
   • Start Outlook in safe mode to rule out add‑ins: press the Windows key, type outlook.exe /safe, press Enter.
   • Try sending from safe mode. If it works there, the issue is likely an add‑in or profile.
   • If problems persist, repair Outlook or the Outlook profile using the guidance in the referenced article, or contact support.

For truly urgent business‑critical issues, contacting Microsoft Support directly is recommended so they can review account‑specific or service‑side problems.

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References:

• I can't send or receive messages in Outlook
• My email message doesn't send
• Outlook email stuck