Mail Getting Caught In Outbox

Question

Hello, I am having issues with my Outlook account where my outgoing emails are getting caught in the outbox. I have followed the steps that were provided, and it is still happening. Also, when it is occurring, my sent folder no longer shows current items, so it is frustrating when I have to send emails, and unless someone lets me know they didn't receive it or follows up, I have no idea. The things that I have tried are

1. Restarting computer & Outlook
2. Ctrl 9 while clicking on the send/receive folder
3. Deleting the account, then reinstalling it (works for a little while, then starts acting up again)
4. Making sure I am connected to the internet, even set to connect automatically.

Any ideas? Please help!

Answer 1

Dear Lundblade, Katherine 

Thank you for reaching out to the Microsoft Q&A forum. I understand your outgoing emails are getting stuck, and when that happens your Sent Items view does not show current sent messages, even after you already tried restarting, forcing Send/Receive, removing/re-adding the account, and confirming internet connectivity. I am happy to assist you. 

Have you tried the AI given steps? Please follow these steps also: 

• Sign in to Outlook.com and send from there until the desktop client is stable again.  
  • If you are using Outlook.com (web).Check whether the stuck message is in Drafts/Outbox and remove any attachment over 25MB (attach a smaller file or upload to OneDrive and attach a link).  
• If your Inbox is full, Outlook.com may not send/receive; free space by emptying Junk Email (right‑click Junk Email > Empty folder).  
• If you are using the Outlook desktop app: isolate add-ins quickly  
  • Start Outlook in Safe Mode and send a test email. If Safe Mode works but normal mode fails, the next step is to disable/remove the problematic add-in(s) 

Please tell me how it goes. If the problem persists, please don’t hesitate to reply to this thread and I will be happy to help. Have a lovely day!   

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Answer 2

Use the following checks and fixes in order, focusing on why messages stay in Outbox and don’t appear in Sent Items.

1. Confirm Outlook is online

• In Outlook, go to Send/Receive.
• Check the Work Offline button:
  • If it’s highlighted/blue, Outlook is offline. Click it once to go back online.
  • After going online, click Send/Receive > Send All and see if items leave Outbox and appear in Sent Items.

2. Fix messages stuck because of size or connection Messages often get stuck due to large attachments or a broken send attempt.

• Select Send/Receive > Work Offline to stop Outlook from trying to send.
• Go to the Outbox folder:
  • Delete any stuck messages, or
  • Drag them to Drafts, open them, and remove large attachments, then save.
• If Outlook says it’s still transmitting, fully close Outlook and ensure it’s not running in Task Manager (end any OUTLOOK.EXE process), then reopen Outlook and repeat the Outbox cleanup.
• When Outbox is clear or messages are reduced, click Send/Receive > Work Offline again to go back online, then resend.

3. Enable automatic sending so items don’t sit in Outbox If messages only send when a manual Send/Receive is triggered, the “send immediately” option may be off.

For Outlook 2010 and later (Classic Outlook for Windows):

1. Select File > Options.
2. Choose Advanced.
3. In the Send and receive section, enable Send immediately when connected.
4. Select OK.

For Outlook 2007/2003:

1. Select Tools > Options.
2. On the Mail Setup tab, in Send/Receive, enable Send immediately when connected.
3. Select OK.

If this checkbox is grayed out, the setting is controlled by Group Policy; an administrator must change it.

4. Check for the “offline” registry issue (Exchange with Cached Mode) If using an Exchange account in Cached Exchange Mode and the issue does not occur in Outlook Safe Mode, a registry value can cause messages to stay in Outbox.

Resolution (advanced – registry edit):

1. Close Outlook.
2. Open Registry Editor.
3. Browse to: HKEY_CURRENT_USER\Software\Microsoft\Office\<x.0>\Outlook\Preferences where <x.0> is the Outlook version (15.0 = Outlook 2013, 14.0 = Outlook 2010, 12.0 = Outlook 2007).
4. If a LoadTransportProviders DWORD exists, delete it.
5. Close Registry Editor and restart Outlook.

Editing the registry is risky; incorrect changes can cause system issues. Only perform this if comfortable with registry edits or with admin support.

5. If Sent Items still don’t show current mail Once messages are actually leaving Outbox and being delivered, they should appear in Sent Items. If they do not:

• Verify that the account you are sending from is the same one whose Sent Items folder is being checked (especially if multiple accounts are configured).
• If the profile has been recreated multiple times and behavior persists, consider having an administrator review any Outlook policies that might affect sending behavior or Sent Items storage.

If the problem continues after these steps, capture whether:

• Messages send only after pressing F9 or Send/Receive, and
• The issue disappears in Outlook Safe Mode.

Those details will help an admin or support engineer narrow it down to either the send-immediately setting, an add-in, or the registry LoadTransportProviders value.

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References:

• Outlook email stuck
• Email stays in the Outbox folder until you manually initiate a send/receive operation in Outlook
• Outlook issues, including reminders that fail to appear, messages stuck in the Outbox, and Desktop Search indexing problems