Sending, receiving, and organizing email in Outlook.com
Hello! Damien. The details will help narrow your issue down, thanks for that. I'm glad to assist you with this.
Outlook for Mac's drag-and-drop functionality works with Safari (and other WebKit-based browsers), but not with Chrome or Firefox. So it's not a browser or Mac bug, it's a compatibility issue between Outlook for Mac and non-WebKit browsers like Chrome.
Short-Term Workarounds:
Use Safari (or another WebKit-based browser like the new Microsoft Edge on macOS), where drag-and-drop from Outlook still works.
Drag to Finder first, then from Finder into Chrome—this works reliably.
Use Outlook’s "Save As…" function to manually export files before uploading them.
For reference, Chrome and Firefox on macOS don't support the specific drag-and-drop interaction implemented in Outlook for Mac. Safari, built on WebKit, aligns more closely with macOS conventions and retains the functionality. Outlook for Mac lacks a toggle for enabling/disabling this drag behavior, no setting exists in Preferences.
See if this helps. If you need more help, just let me know.
Best regards,
Kimberly