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Why Are My Outlook Emails Not Sending and Going to Drafts?

  Rollins Duke
Rollins Duke   
Published: October 31st, 2025 • 5 Min Read

As lots of users facing Outlook emails not sending issues, it usually prevents messages from leaving the outbox and reaching the recipient’s mail server. This issue mostly happens due to incorrect account settings, connectivity issues, corrupted Outlook profiles or large attachments can also be the reasons of Outlook emails not sending from outbox or scheduled emails not sending.

Understanding why Outlook emails are not sent is the first step toward fixing the issue. In most cases, it’s not a permanent failure, it requires troubleshooting because of server configuration, network glitch or mailbox synchronization error.
In this tutorial, we will explain what’s actually happening. Outlook won’t send your emails, how to identify the problem and tested methods to fix Outlook emails not sending or receiving issues.

Table of Content Hide
  1. Check Your Connectivity: Is Outlook Connected or Working Offline??
  2. Check Your Internet or Server Connection
  3. Verify Outgoing Mail Server Settings
  4. Large Attachment or Bulk Messages Blocking the Send
  5. Authentication Problems: Password or Account Access
  6. Outlook Profile or Application Corruption
  7. When Your Outlook Profile is Damaged?
  8. Repair or Recreate Outlook Profile
  9. Remove Suspicious Add-ins
  10. How to Identify Outlook Stuck Messages?
  11. Check for Updates
  12. Conclusion

Check Your Connectivity: Is Outlook Connected or Working Offline?

Sometimes the reasons your Outlook emails aren’t sending is surprisingly simple: you are just offline. If Outlook can’t reach the internet or mail server, your messages will sit in the Outbox until it reconnects.

  1. Launch Outlook Offline Mode
  2. Open Outlook and navigate to the Send/Receive tab.
  3. Look for the Work Offline Button.
  4. If it’s highlighted, click it once to go back online.

Check Your Internet or Server Connection

  1. Open your browser and visit any website to confirm your internet is working.
  2. If you’re using Office WIFI, Ask your Admin if the mail server is down.
  3. Restart your router or switch to another network if needed.

Verify Outgoing Mail Server Settings

  1. Launch Outlook and click on Account Settings and press on Server Settings.
    click on account settings
  2. Make sure the Outgoing Mail Server(SMTP) section matches your provider’s official info.
  3. Double cheek server name, port number, encryption, and authentication.

Large Attachment or Bulk Messages Blocking the Send

  1. As most email servers have an attachment limit of 20-25 MB.
  2. Now, compress your files into a ZIP folder.
  3. Upload large files to OneDrive, Google Drive or Dropbox and share the link instead.
  4. Delete unnecessary attachments or images before hitting send.

Authentication Problems: Password or Account Access

  1. Click on file and press on Account Settings.
    click on file
  2. Press Update Password and fill your recent password.
  3. Click on Test Account Settings to make sure everything connects properly.

Outlook Profile or Application Corruption

  1. If you checked your internet settings, password and your emails won’t send the problem might be with Outlook itself.
  2. A corrupted Outlook profile or damaged data file(OST or PST) can easily stop messages from being sent or synced.

When Your Outlook Profile is Damaged?

  1. Your Outlook Profiles stores all your account settings, preferences and data links.
  2. If it becomes corrupted, Outlook can’t process outgoing emails correctly.
  3. Outlook emails get stuck in the outbox.
  4. Repeated Send/Receive error.
  5. Outlook freeze or unexpected closure.

Repair or Recreate Outlook Profile

If you want to repair your Outlook profiles then we recommend you to choose BitRecover PST Repair Tool as it can repair any number of damaged Outlook files and it also offers fully maintained accuracy as appears in your Outlook file.

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  1. Download and launch Recommended Tool on your system.
    launch recommended software
  2. Click on Select files or folder to browse PST file.
    select pst file
  3. Select the PST folder as you need in the repaired Outlook file.
    select outlook folder
  4. Choose destination and hit Next to start repairing Outlook profiles and now you can send or receive emails in Outlook.
    choose destination path

Remove Suspicious Add-ins

  1. Run Outlook and click on the file.
    open outlook
  2. Hit on Options and press on Add-ins.
    click on options
  3. Select COM:Add-ins and press on Go.
    click on COM Add-ins
  4. Uncheck faulty add-ins and try to resend Outlook emails.
    disable faulty add-ins
How to Identify Outlook Stuck Messages?

You’ll usually see the email listed in your Outbox with a paper clip icon(if it has an attachment) or bold text. If you double-click the message and it won’t open, it’s stuck.

  1. Navigate to Send/Receive and hit Work Offline.
  2. Open the stuck email in the outbox and delete or move it to drafts.
  3. Switch Work Offline off again.
  4. Recreate a New Email and send it fresh.
  5. When Outlook sending limit reached, server downtime, Outlook mailbox full or outdated version of Outlook.
Check for Updates
  1. Launch Outlook, click on file and hit on Office Account.
    click on office account
  2. Hit on Update options and press on Update Now.
    click on update now
Conclusion

In this guide, we’ve explained all the tried and tested methods to fix Outlook email sending errors. We’re confident that after following these steps, you’ll be able to resolve the issue effectively without any risk of losing your data.


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