If you’re one of the many folks who used to drag email attachments from Outlook straight into your CRM like a digital magician pulling files out of a hat, and then suddenly found that trick doesn’t work anymore, you’re not losing your touch. You’re just using New Outlook.
Welcome to the “It Worked Yesterday” club.
So, What Broke Outlook?
New Outlook broke it. Or more accurately, Microsoft broke it on purpose. Their reasons that are actually pretty sensible, even if they’re wildly inconvenient.
New Outlook ≠ Old Outlook
Classic Outlook (the OG desktop app) was a proper Win32 application. It did things the old-school way: attachments got saved to a temp folder on your machine. That made it easy to grab them and drop them wherever you pleased, including into a browser window running HubSpot, Salesforce, Bullhorn, or whatever flavour of web-based CRM you’re using.
New Outlook, on the other hand, is built on the same codebase as Outlook on the Web (OWA). Yes, the app you install is basically a glorified browser in a trench coat.
This means:
- No more dirtying up your temp folders with file detritus.
- Tighter security sandboxing.
- A consistent experience across Windows, macOS, and browsers. Hooray for design teams, less so for power users.
Why Drag-and-Drop Fails in New Outlook
Here’s the technical but:
- No Local Temp Files: Dragging a file in Classic Outlook created a local file. Dragging in New Outlook doesn’t because the app doesn’t store it locally in the same way.
- Sandboxed File Access: New Outlook doesn’t let other apps (like your browser) reach in and grab file handles.
- Microsoft Wants You in the Cloud: Outlook now prefers you share links via OneDrive or SharePoint. Physical attachments? So last decade.
- Cross-Platform Parity: Features like drag-and-drop that depend on OS-level behaviour? Those are getting the axe in favour of sameness across platforms.
What You Can Do Instead
Alright, so drag-and-drop is toast (for now). What are your options?
Download First, Then Upload
Yeah, it’s one extra step. Drag it onto your desktop first, then drag it into your CRM. Old-fashioned, but effective.
Stick with Classic Outlook
Until Microsoft pries it from your cold, carpal-tunnelled hands, Classic Outlook still supports drag-and-drop the way nature intended.
Forward to CRM
Many CRMs support email forwarding. Just shoot that email (attachments and all) to your CRM’s magic ingest address.
Use File Explorer
Already downloaded the attachment? Open File Explorer (or Finder), and drag from there into your CRM. Works every time.
TL;DR
New Outlook is a sleek, secure, cloud-loving app that doesn’t play well with old-school drag-and-drop behaviour. It’s not a bug. It’s a feature. A frustrating, productivity-punching feature.
Welcome to modern software. Bring snacks and a workaround.
