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My email will no longer send if I attach photos.

Mellie 5 Reputation points
2026-05-05T12:28:06.58+00:00

I have Windows 10 and Outlook. My emails have always sent with attached photos and have stopped suddenly. I have always been able to send 5 or 6 photos at a time. Thinking the file was too large this time, I tried to send only one photo, but it got stuck in my outbox too. I can still receive emails and send emails without attachments. Any help will be appreciated.

Outlook | Windows | Classic Outlook for Windows | For home
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  1. Alice-N 9,285 Reputation points Microsoft External Staff Moderator
    2026-05-06T07:56:42.0133333+00:00

    Hi Mellie

    I understand you’re having an issue where emails get stuck in the Outbox only when photos are attached in Classic Outlook for Windows (Windows 10), while emails without attachments send normally. Could you confirm:

    • What type of account is configured in Outlook (e.g., Outlook.com, Gmail, Yahoo, or an ISP POP/IMAP account)?
    • While the message is stuck, is Send/Receive > Work Offline enabled (blue)?

    I would love to hear from you soon. Have a lovely day!


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