Drag and drop email to To Do or Calendar is a core productivity workflow in New Outlook, but many users are reporting that it suddenly stops working without explanation. If drag-and-drop feels unreliable—or completely broken—you’re not alone. This issue is tied to how the My Day pane loads and initializes, not to anything you configured incorrectly.
The Problem
Drag-and-drop email to To Do or Calendar via the My Day pane intermittently stops working in New Outlook. This issue was reported in late December 2025. I also experienced this problem.
What makes this frustrating:
- There’s no error message
- It works sometimes and fails other times
- Restarting Outlook doesn’t consistently fix it
- The feature appears available but isn’t actually ready
From the user’s perspective, everything looks normal—until nothing happens.
What’s Really Causing It
The My Day / To Do pane often hasn’t fully initialized, even when it looks loaded.
When this happens:
- Drag-and-drop silently fails
- Behavior varies between sessions
This points to a timing and background loading issue, not a removed feature or user mistake.
Microsoft is aware of this issue and is actively working on improving performance and stability.
What Works (For Now)
Until Microsoft stabilizes this behavior, this is the most reliable workaround:
Open New Outlook
Open the My Day pane
Wait until all tasks fully load
(This can take longer than expected—even hours in some cases)Reboot New Outlook
Try dragging the email into the To Do pane or Calendar
Once drag-and-drop starts working, it usually remains stable. However, I am still seeing a 20 to 30 second delay with loading My Day. (I guess that’s better than nothing.)
Bottom Line
If dragging emails into To Do or Calendar feels inconsistent, that’s because it is.
Microsoft is working on improving the performance, but for now, this is a limitation you need to plan around in New Outlook—especially if email-to-task or email-to-calendar workflows are critical to how you work.
Now go and work your magic. 
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