Using New Outlook on Windows for personal email, calendar, and contact management
Welcome to Microsoft Q&A.
Thanks for sending the details and screenshots — that really helps me a lot.
This behavior matches how Office “Send as Attachment” works today: Word/Excel/PowerPoint use the legacy Windows mail handoff (MAPI), which Classic Outlook supports. New Outlook is essentially a web-based app (PWA) and doesn’t support that same local handoff, so Office routes the action through Classic Outlook instead.
Quick heads-up: If the message is created in Classic Outlook, it will sit in Classic Outlook’s Outbox and won’t send until Classic Outlook is opened. It’s easy to assume it’ll send in the background, which can explain the “days later” timing.
Workaround for New Outlook users: Start the message in New Outlook, then attach the file (Attach button or drag & drop).
Tip: Attach the file using the Attach button or by dragging it in from File Explorer or OneDrive. Or, if it fits your workflow, use Office “Send a link” instead of “Send as attachment.”
Please let me know if this proves useful to you, or if you would like further assistance.
I'm looking forward to your reply.