Share via

emails are stuck in the outbox

Beth Bell 0 Reputation points
2026-04-03T14:38:06.46+00:00

when I send an email it is staying in the outbox and not sending

Outlook | Windows | New Outlook for Windows | For business

2 answers

Sort by: Most helpful
Most helpful Newest Oldest
  1. Alexis-NG 16,185 Reputation points Microsoft External Staff Moderator
    2026-04-03T15:31:19.25+00:00

    Hi @Beth Bell,

    Good day and thank you for reaching out.

    As you are using New Outlook, additional details are required to narrow down the issue and provide more accurate assistance. Could you please confirm the following:

    1. Are you using a work/school account (Microsoft 365 / Exchange) or a personal account (Outlook.com, Hotmail, Gmail, etc.)?
    2. Does this happen with all emails, or only with specific emails (for example, ones with attachments or sent to certain recipients)?
    3. Do the stuck messages include attachments? If yes, approximately how large are they and what file types are attached?
    4. If you sign in to Outlook on the web using the same account, are you able to send emails successfully from there?
    5. In New Outlook, does the account show as Connected, or do you see anything like “Offline” or “Queued” on the message?
    6. Does the account show as Connected in New Outlook settings, and are you prompted to sign in again at any point?
    7. Does the same issue occur on another device or on a different network (for example, home vs. office)?

    Once these points are confirmed, it becomes much easier to determine whether the issue is:

    • A New Outlook session/authentication problem
    • A message or attachment‑specific block
    • An account or service‑side sending issue

    Once I have a clearer understanding of your current situation, I’ll be happy to assist you with greater accuracy. Please feel free to share any additional details you believe are relevant. Screenshots are especially helpful and much appreciated.

    Thank you for your patience and your understanding. If you have any additional questions, please feel free to reach out. 

    I'm looking forward to your reply. 

    Was this answer helpful?

    0 comments

  2. AI answer

    2026-04-03T14:38:19.82+00:00

    Use these checks and fixes in order:

    1. Confirm Outlook is online
    • In Outlook, go to Send/Receive.
    • Check the Work Offline button:
      • If it is highlighted/blue, Outlook is offline. Click Work Offline once to go back online, then click Send All.
    1. Check for large or problematic messages in Outbox
    2. Select Send/Receive > Work Offline to stop Outlook from trying to send.
    3. Open the Outbox folder.
    4. For any stuck message:
      • Either select it and press Delete, or
      • Drag it to Drafts, open it, and remove large attachments, then send again.
    5. If Outlook says it is still transmitting and will not let the item be edited or deleted:
      • Close Outlook and wait a few moments.
      • If it will not close, use Ctrl+Alt+Delete → Task Manager → Processes tab → select outlook.exe → End Process.
      • Reopen Outlook, repeat steps 1–3, then click Send/Receive > Work Offline again to go back online.
    6. Enable automatic sending when connected
    7. Select File > Options.
    8. Select Advanced.
    9. In Send and receive, enable Send immediately when connected.
    10. Select OK, then try sending again.
    • If this option is greyed out, it is controlled by Group Policy; contact the administrator to change it.
    1. If Outlook is in Cached Exchange Mode and behaves differently in Safe Mode If messages send correctly when Outlook is started in Safe Mode, and the mailbox is an Exchange account using Cached Exchange Mode, a registry setting may be causing the issue. The documented fix is to remove the LoadTransportProviders value:
    2. Open Registry Editor.
    3. Go to HKEY_CURRENT_USER\Software\Microsoft\Office\<x.0>\Outlook\Preferences (replace <x.0> with the Outlook version, for example 15.0, 14.0, or 12.0).
    4. Right‑click LoadTransportProviders (DWORD) and select Delete.
    5. Close Registry Editor and restart Outlook.

    Editing the registry is risky; incorrect changes can cause serious system problems. Only perform this step if comfortable with registry editing and after taking appropriate backups.

    If emails are still stuck after these steps and the account is in Microsoft 365/Exchange Online, check with the Microsoft 365 admin or support, as there may be a mailbox‑level or third‑party add‑in issue.

    References:

    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.