emails are stuck in my outbox since I updated my licence

Susan Grayson 0 Reputation points
2026-10-01T21:43:11.17+00:00

Since updating my licence emails are not sending, they remain stuck in the outbox

Outlook | Windows | Classic Outlook for Windows | For business
0 comments

2 answers

Sort by: Most helpful
Most helpful Newest Oldest
  1. Ivory 1,825 Reputation points Independent Advisor
    2026-10-01T21:52:08.4833333+00:00

    Hi Susan,

    To better understand what's happening, could you provide a few more details?

    • What license was updated (Microsoft 365 Business Basic, Business Standard, Exchange Online, etc.)?
    • Do all emails remain stuck in the Outbox, or only messages sent to certain recipients?
    • Do you receive any error messages, Non-Delivery Reports (NDRs), or synchronization errors?
    • Can you send emails successfully using Outlook on the web?

    To ensure I provide the most accurate assistance, I would appreciate any additional information you can share regarding your current situation. If possible, please include screenshots, as they can be very helpful in the investigation.

    In the meantime, please try the troubleshooting steps outlined in the article below and let me know if any of them help resolve the issue. Outlook email stuck | Microsoft Support

    Thank you for your patience and understanding. Should you have any further questions, please feel free to comment on this post at any time.

    If the answer is helpful, please click 'Yes' and kindly upvote it.

    Note: Please follow the steps in the forum documentation to enable e-mail notifications if you want to receive the related email notification for this thread. 

    Was this answer helpful?

    0 comments

  2. AI answer

    2026-10-01T21:43:30.23+00:00

    For classic Outlook on Windows, the most common supported checks are:

    1. Verify Outlook is not offline.
      • Go to Send/Receive.
      • If Work Offline is highlighted, select it to go back online.
      • Then select Send All.
    2. Check whether a large attachment is blocking the Outbox.
      • Go to Outbox.
      • Open the oldest stuck message first.
      • If it has a large attachment, remove the attachment or replace it with a smaller file.
      • A large stuck message can also block messages sent after it.
    3. Re-enable automatic sending.
      • Go to File > Options > Advanced.
      • Under Send and receive, make sure Send immediately when connected is enabled.
      • If this option is grayed out, it is being managed by Group Policy and an administrator must change it.
    4. Check for a delayed-send rule.
      • Go to Rules on the ribbon > Manage Rules & Alerts.
      • Review rules on the Email Rules tab.
      • If a rule shows defer delivery by # minutes, open that rule and clear that action if it is not intended.
    5. Confirm internet connectivity.
      • Open a browser and verify normal internet access.
      • If the device is offline, Outlook cannot send mail.
    6. If the issue started after the license change and Outlook sync errors are also appearing:
      • Check the Sync Issues folder for errors such as 80040611.
      • If that specific error is present, the documented mitigation is to pause Digital Guardian if it is in use, then request a mailbox move through the Microsoft 365 Admin Portal and recreate the Outlook OST. This requires opening a support case.
    7. If Outlook only stays offline in normal mode and not in Safe Mode:
      • There is a documented case involving the LoadTransportProviders registry value.
      • Warning: deleting registry values is risky and incorrect changes can cause system problems.
      • The documented fix is to delete LoadTransportProviders from: HKEY_CURRENT_USER\Software\Microsoft\Office\<x.0>\Outlook\Preferences

    Since the problem began after a license update, start with steps 1, 3, and 6 first, because they best match a send/sync change rather than just a single bad message.

    AI-generated content may be incorrect. Read our transparency notes for more information.

    Was this answer helpful?

Your answer

Answers can be marked as 'Accepted' by the question author and 'Recommended' by moderators, which helps users know the answer solved the author's problem.