Using the New Outlook for Mac for personal email and calendar
Hi RW_hwk,
Thank you very much for your update and your patience. I sincerely apologize for the delay in getting back to you, and I truly appreciate all your effort in trying to resolve the issue.
Since the drag-and-drop to upload works in one environment but not in others, it suggests this may be related to recent changes in how the new Outlook app interacts with different web upload interfaces on macOS. Currently, there is no specific setting within Outlook for Mac that controls drag-and-drop behavior across all browsers or upload fields.
To help improve the product, I recommend submitting feedback through the How do I give feedback on Microsoft 365? - Microsoft Support. This will ensure the product team is aware of the issue and can investigate for future updates.
As a temporary workaround, you can consider to continuing to save the file locally and then uploading it manually.
Please let me know if you need any assistance or have other questions.
Best regards,
Mia - MSFT | Microsoft Community Support Specialist