Emails stuck in Outbox, have to end task & reopen to send then frequently disappears from Outbox but never arrives & does not appear in Sent folder. Where are these emails & how to repair? Thanks!

Question

Sent emails get stuck in Outbox, have to end task & reopen Outlook for them to send, THEN they frequently disappears from Outbox but never arrive & do not appear in Sent folder. Where are these emails & how to repair? And yes it happens with attachments (small not over 1mb) & without attachments & indiscriminate as to who email is sent to. Have read about deleting account & remaking but cannot lose existing emails & no explanations address the details of doing that. Thanks!

Answer 1

Emails getting stuck in the Outbox in Outlook can be caused by several issues. Here are some steps you can take to troubleshoot and potentially resolve the problem:

1. Check Your Connection: Ensure that you have a stable internet connection. Sometimes, connectivity issues can prevent emails from being sent.
2. Send/Receive All Folders: Try manually performing a Send/Receive operation. You can do this by clicking on the Send/Receive button in Outlook.
3. Outlook Profile: If your Outlook profile is set to online mode, and you are using the DelegateSentItemsStyle registry value set to 1, this can cause emails to remain in the Outbox. Consider changing your profile settings or registry values if applicable.
4. Reset Folders: You can run Outlook.exe /resetfolders and Outlook.exe /resetfoldernames to reset your folder settings, which may help resolve issues with emails not being sent or appearing in the Sent folder.
5. Check for Cached Mode Issues: If you are using Cached Exchange Mode, sometimes emails may not appear in the Sent folder due to synchronization issues. Ensure that your Outlook is properly synchronizing with the server.
6. Check for Large Attachments: Although you mentioned that your attachments are small, it's worth noting that even small attachments can sometimes cause issues if there are other underlying problems with the email server or Outlook itself.
7. Repair Outlook: If the problem persists, consider repairing your Outlook installation through the Control Panel. This can fix corrupted files that may be causing the issue.
8. Backup Emails: Before making significant changes, such as deleting and recreating your account, ensure you back up your existing emails to avoid data loss.

If these steps do not resolve the issue, you may need to consult with your IT department or consider reaching out to Microsoft support for further assistance.

---

References:

• Email messages are stuck in Outbox in Outlook 2016 for Mac
• Sometimes emails do not appear in Cached mode Inbox even if they were synchronized down from mailbox
• Email remains in the Outbox when you use the DelegateSentItemsStyle registry value

Answer 2

How do you backup emails?

Answer 3

Thanks for sharing the details! Try to disable ALL add-ins

This issue is very commonly caused by add-ins, especially antivirus and PDF tools.

Steps

• Close Outlook
• Press Win + R
• Run:
  outlook.exe /safe
• Send multiple test emails

If it works in Safe Mode:

• Open Outlook normally
• File → Options → Add-ins
• At bottom: COM Add-ins → Go
• Uncheck ALL add-ins
• Restart Outlook
• Re-enable add-ins one by one

High-risk add-ins

• Antivirus email scanning
• Adobe / PDF add-ins
• CRM plugins
• Old signature managers

If disabling add-ins fixes it, this is 100% your root cause.

See if this helps. If you need further assistance just let me know.

Best regards,

Kimberly