Dear POLANCO JORGE
Thank you for reaching out to the Q&A Forum. I understand how stressful it can be when emails get stuck in the Outbox, especially when you need something sent urgently. Please try these standard steps below to see if they help get your messages sending again:
1> Use Work Offline to clear stuck messages: Go to Send/Receive and select Work Offline (turn it on temporarily). Navigate to Outbox and drag any stuck emails to Drafts. Open each message in Drafts and remove large attachments or replace them with OneDrive/SharePoint links. Close the message, then reconnect by going to Send/Receive and toggling Work Offline off (back online). Click Send/Receive All Folders and resend the email.
2> Check Send/Receive settings: Go to File > Options > Advanced, scroll to the Send and receive section, make sure “Send immediately when connected” is checked, click OK, and try sending again.
3> Start Outlook in Safe Mode: Add-ins can sometimes interfere with sending emails, and Safe Mode disables third-party add-ins. Press Windows + R, type the command outlook.exe /safe, and press Enter. Send a test email (ideally with a small attachment). If it works in Safe Mode, an add-in is likely the cause, so disable unnecessary add-ins by going to File > Options > Add-ins, then at the bottom choose Manage: COM Add-ins and click Go, uncheck add-ins you don’t need, restart Outlook normally, and test again.
4> Move or delete the stuck email: Open the Outbox, then drag the stuck email into the Drafts folder. Open it from Drafts and either remove any large attachment(s), replace large attachments with a cloud link (OneDrive/SharePoint), or delete the message if you no longer need it. Save and close the message, then try sending again.
5> Repair the Office installation: Go to Control Panel > Programs > Uninstall a program, right-click to Microsoft Office, choose Change, then Repair. Run Quick Repair first, and if it’s still not resolved, run Online Repair. Open Outlook and test again.
6> Delete LoadTransportProviders in Registry
This addresses a specific registry value that, if set or corrupted, can override Outlook’s normal sending behavior. Please note that editing the registry carries risk, so it’s strongly recommended to back up before making changes. Press Windows + R, type regedit, and press Enter. Navigate to the path HKEY_CURRENT_USER\Software\Microsoft\Office\<version>\Outlook\Preferences, look for a DWORD named LoadTransportProviders, and if it exists, right-click it and choose Delete. Restart Outlook and test sending again.
Hope this helps. If any of these solutions work, please let me know which step resolved the problem, your feedback is valuable in helping other users who may run into the same client-specific issue. If the problem persists, feel free to share an update (including any error message or what Outlook shows in the status bar), and I’ll be happy to help you with further advanced diagnostics.
Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.