Outlook Messages Stay in Outbox When Sending

  

Rollins Duke   
Published: May 28th, 2025 • 7 Min Read

Are you facing issues with Outlook messages staying in Outlook when sending or Outlook messages sent but staying in outbox IMAP or refuse to send. Don’t worry this is the common problem that can affect your workflow, delay communication and create frustration. Especially when email is sensitive. Understand reasons behind this error and also provide proven methods to help you to fix the issues quickly

When you hit the Send button in Outlook, your message is first stored in the Outbox, where it waits until Outlook connects to the mail server to complete the delivery. If emails remain in the Outbox, it usually indicates an issue—such as a connection problem, problematic message content, or an application-related error. Stay with us until the end, and you’ll get a clear solution to fix the Outlook message sent but stays in Outlook IMAP with this article.

Common Reasons Why Outlook Messages Stay in Outbox

• If Outlook can’t connect to the server due to weak or lost connectivity, the email won’t leave the outbox.
• Oversize attachments can delay sending, especially if they exceed the limit set by your mail server.
• If Outlook works in offline mode it will queue email in the outbox until you’re back online.
• A damaged profile can prevent normal sending and receiving emails.
• If your mailbox is full, you won’t be able to send new messages.

How to Fix Outlook Messages Stay in Outbox When Sending?

If you want to fix Outlook message sent but stays in Outbox IMAP then follow the procedure as we have explained below:

Method 1. Check Connectivity

1. Verify your device has stable Connectivity.
2. Open the Browser and visit any website to confirm Internet access.
3. If it shows No Connectivity then restart the router or contact your ISP.

Method 2. Switch Outlook to Online Mode

1. Open Microsoft Outlook.
2. Go to the Send/Receive button option.
3. If the work offline button is highlighted, click it and go Back Online.
4. You should see connected to Microsoft Exchange in the status bar.

Method 3. Reduce Attachment Size

1. Open a stuck email in Outbox by double clicking on it.
2. If an attachment is larger than 20 MB, remove them.
3. Compress files into a ZIP folder or upload them to OneDrive, Dropbox or Google Drive.
4. Click Send again.

Method 4. Open and Resend Email

1. Go to the Outbox folder.
2. Double click on Email to open it.
3. Make small changes like Adding space or full stop.

Method 5. Relaunch Outlook

1. Close Outlook completely.
2. Wait for a few seconds and relaunch Outlook.
3. Go to Outbox and check if a message is sent automatically.

Method 6. Clear Outbox and Recreate Email

1. Right-click on email in the Outbox and select delete.
2. Go to drafts or new Email and recreate your message.
3. Click on Send Again.

Method 7. Disable Problematic Add-ons

1. Open Outlook and navigate to file and press options.
2. Click on Add-ons and navigate to click Go.
3. Manage Com Add-ins and remove unnecessary or suspicious add-ons.

Method 8. Temporarily Disable Antivirus

1. Open Antivirus and temporarily disable antivirus scanning or firewall settings.
2. Go back to Outlook and try resending email.

Method 9. Repair Outlook Profile

1. Close Outlook.
2. Go to the Control Panel and click on Mail(Microsoft Outlook).
3. Press on Show Profiles and select your current profiles and click Repair.
4. Follow prompts to complete the Repair.
5. Relaunch Outlook and check Outbox email has gone or appear in Outbox.

Method 10. Update Outlook Version

1. Open Outlook and navigate to file and click on Account Settings.
   
2. Now, Click on Office Account.
3. Press on Update options and click on Update Now.
4. Wait for the update process to complete, then relaunch Outlook.

How to Recover Corrupted Outlook Messages Using Automated Approach?

As Outlook messages stay in Outlook when sending it also happens when Outlook files get corrupted. So, we recommend you to choose BitRecover PST Repair as this software supports Recovery mode to recover and restore deleted emails from Outlook.

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Steps to Fix Recover Corrupted Outlook Messages

1. Download and open automated software on your pc.
2. Click on select files or folder to upload Outlook files.
3. Now, choose Outlook mailbox folders as you want to repair.
4. Select saving option and destination path as per needed.
5. Now, press on the Repair button to restore all corrupted Outlook data.

Notable Attributes of Automated Software

• This software allows you to convert individual or batch Outlook files at once.
• It is specially designed with a simple initiative interface to easily perform by any professional or individual users.
• You can also convert PST to PDF, HTML, MBOX, EML, HTML, RTF and many more.
• This wizard also allows you to use file naming options for individual email files such as EML, PDF, MSG, and many others.
• It allows you to import PST to Microsoft 365, Lotus Notes, Zimbra, and Thunderbird.

Helpful Questions & Answers

Why do Messages Keep Getting Stuck in the Outbox?

Emails may get stuck in the outbox due to poor connectivity, large attachments or an issue with your Outlook profile. Also, Antivirus programs or incorrect settings can stop the process.

Why does Outlook say I have Messages in my Outbox?

Outlook shows messages in your Outbox when emails haven’t been yet. This could be due to being offline, connection issues, or email errors. Until successfully sent, those emails remain in the outbox.

Why are all my Emails going to the Outbox and not Sending?

If all emails go to Outbox but don’t send, check your connectivity, server settings and account authentication. A misconfigured account or interference from antivirus/firewall could also be a reason.

How do I fix an Outlook email that is Stuck in my Outbox?

First, check your connectivity and switch to online mode if required. Then try resending or moving messages to drafts. Relaunch Outlook and check for large attachments. Repairing your Outlook profile may also help.

How do I fix a stuck email in Outlook Outbox on Mac?

Go to the Outbox folder and double click on check email, and try resending. If that fails, drag it to drafts then reopen and send it again. Also, check Outlook is online and have stable connectivity. Restart Mac Outlook if needed.

Preventive Measures to Avoid Future Occurrences

• Keep Outlook updates to fix bugs and get faster performance
• Check email size, especially attachments that exceed the server’s capacity.
• Disable Outlook unnecessary add-ons to reduce conflict and Outlook performance.
• Periodically check and repair your Outlook profile to avoid corruption and send/receive errors.

Special Consideration for Outlook on Mac

• Use Microsoft database to recreate Outlook database and fix performance issues.
• Verify Outlook is properly connected with the server, especially for Exchange or IMAP accounts.
• Understand that Outlook for Mac may delay sending until the app is open and connected as compared to Windows.

Conclusion

In this guide, we outlined the best approaches to fix Outlook messages that stay in Outbox when sending. Try manual approaches to fix this error if not done manually. Then, it mostly happens due to the Outlook file being corrupted. So, opt automated software as it can restore and recover deleted items and also a completely reliable choice to restore highly corrupted PST files.