How to get emails unstuck from hotmail outbox

Open each stuck message in the Kindle Fire Outlook app, remove any large attachment, and tap Send again; if it remains stuck, delete it from Outbox and resend it as a new message.

Clear the stuck message

1. Confirm the Kindle is connected to Wi-Fi.
2. Open Outlook → Outbox.
3. Open the stuck email:
   • Copy important text before deleting anything.
   • Remove its attachment, especially if it is larger than 25 MB, which Outlook.com cannot send.^1^
   • Tap Send again.
4. If it still does not send, delete it from Outbox, create a new message without the attachment, and send that.

Determine whether Outlook or the Hotmail account is affected

In the Kindle browser, open https://outlook.com, sign in, and send a short test message to yourself.

• The browser message sends: The Hotmail account is working, so reset the Outlook app connection.
• The browser message also fails: Check the error displayed there. Confirm Microsoft cloud storage is not full and that the message has no attachment over 25 MB. Full cloud storage prevents sending and receiving.^1^

Reset the Outlook connection

In the Outlook app:

1. Tap the profile picture → Settings → Accounts.
2. Select the Hotmail account.
3. If Reset Account is available, tap it and let Outlook restart.
4. Send another small test message.

If resetting does not work:

1. Return to Settings → Accounts → Hotmail account.
2. Tap Delete Account → Delete From This Device. This removes the account from the Kindle, not the mailbox stored online.
3. Add the account again and choose Outlook.com rather than manually configuring it as POP or IMAP. Microsoft’s mobile guidance recommends removing the sync partnership and re-adding the account when a previously working Outlook.com account stops syncing.^2^

A Kindle Fire case with the same Outlook/Hotmail synchronization problem also recommends removing and re-adding the account as Outlook.com or Exchange ActiveSync, enabling automatic date and time, and allowing background activity.^3^

If messages still remain queued

• Go to Kindle Settings → Device Options → Date & Time and enable automatic date, time, and time zone.
• Go to Settings → Battery, find Outlook, and allow background activity or remove battery restrictions.
• Update Outlook through the Amazon Appstore if an update is offered.
• Continue using Outlook.com in the Kindle browser while the app is not synchronizing.
• In Outlook mobile, use Settings → Help & Feedback → Contact Support. Microsoft directs Hotmail and other Outlook.com users to Microsoft Support for unresolved mobile synchronization problems.^2^

References

1. Can't send or receive email in Outlook.com
2. Troubleshoot Outlook mobile issues | Microsoft Support
3. Outlook app on kindle fire stopped accessing email from server - Microsoft Q&A