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!