I have emails in my outbox in outlook, which wont send.

Robert Horne 0 Reputation points
2026-03-20T14:39:57.02+00:00

Can you tell me why? I have tried, and tried, but they just wont send?! Whilst writing I am told, by my bank, that my payment card needs updating with you guys. Can you please let me knowhow I do this?

Microsoft 365 and Office | Subscription, account, billing | For home | Windows
0 comments No comments

1 answer

Sort by: Oldest
  1. AI answer

    2026-03-20T14:40:09.7533333+00:00

    For emails stuck in the Outlook Outbox, use these checks and fixes:

    1. Confirm Outlook is online
    • Look at the status bar at the bottom of classic Outlook.
    • If it shows Disconnected, Working Offline, or Trying to connect…, Outlook cannot reach the mail server.
    • Go to the Send/Receive tab on the ribbon and select Work Offline once to toggle back online.
    • Then choose Send/Receive or open the stuck message and select Send again.
    1. Check internet connection
    • Open a browser (Microsoft Edge or Google Chrome).
    • Browse to a site such as http://www.microsoft.com or http://www.bing.com.
    • If websites do not load, resolve the network issue first. Outlook cannot send mail without internet access.
    1. Check for large attachments
    • Some providers block large messages (often around 20–25 MB).
    • In Outlook, open the Outbox.
    • Start with the oldest stuck message.
    • If it has an attachment larger than about 20 MB, delete the attachment.
    • Reattach a smaller file or upload the file to a cloud service and send a link instead.
    • Send the message again.
    1. Enable automatic sending (classic Outlook on PC) If messages only send when manually doing Send/Receive:
    • Select File > Options.
    • Select Advanced.
    • In Send and receive, enable Send immediately when connected.
    • Select OK.

    If this setting is greyed out, it is controlled by an administrator and must be changed by that admin.

    Regarding updating a payment card The provided information does not cover payment card or billing update steps. For card or billing updates, use the official Microsoft account and billing channels only and follow the instructions provided there, not links in emails or messages.


    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.