How to get emails unstuck in HOTMAIL account

Open the Hotmail mailbox directly in Outlook.com, remove the stuck message from Outbox, and resend it first as a plain-text message without attachments.

Release the stuck email

1. Sign in to Outlook.com with the affected @hotmail.com account—not the Outlook account that is working.
2. Open Outbox. If the message is instead under Drafts, open it there.
3. Delete the stuck message, or open it and remove its attachment.
4. Create a new test email containing only plain text and send it to another address you control.
5. Check whether it moves to Sent Items or remains in Outbox.

An attachment larger than 25 MB cannot be sent through Outlook.com. Use a smaller attachment or upload the file to OneDrive and send a link instead.^1^

If the plain-text test is also stuck

Check the affected Hotmail mailbox’s storage:

1. In Outlook.com, select Settings.
2. Open General → Storage. In some layouts, this appears as Accounts → Storage.
3. If storage is full, permanently remove unneeded mail and empty Deleted Items and Junk Email.
4. Send another plain-text test message.

A full Microsoft cloud storage allocation prevents the account from sending or receiving email.^2^

If storage is available, note any error or non-delivery report. It can identify an account restriction, recipient problem, or server rejection. A temporary account block can also occur after unusual sign-in activity.^2^

If it works on the web but not in an Outlook app

That result isolates the issue to the app’s connection or synchronization rather than the Hotmail mailbox.

• Outlook on Windows or Mac: select Send/Receive → Send/Receive All Folders.^1^
• If the message still cannot be deleted, select Send/Receive → Work Offline, delete it from Outbox or move it to Drafts, remove the attachment, and then turn Work Offline off before resending.^3^

Escalation

If a plain-text message remains stuck in Outlook.com even though storage is available, select Help on the Outlook.com menu bar, enter the sending problem, and complete the self-help prompts. If unresolved, scroll to Still need help? and select Yes. Include the exact error text, but remove email addresses and other personal information.^1^

References

1. Email stuck in Outlook.com | Microsoft Support
2. Can't send or receive email in Outlook.com | Microsoft Support
3. Outlook email stuck | Microsoft Support