Hi @Gary Skybo,
Welcome to Microsoft Q&A forum.
Thank you for reaching out and sharing your feedback about attaching files in Microsoft Planner. I completely understand how inconvenient it can feel to save an attachment first just to add it to a task.
Currently, Planner does not support drag-and-drop attachments directly from Outlook or other apps. This is because Planner stores attachments as links to files in SharePoint or OneDrive, rather than embedding the file itself. This design ensures secure storage and collaboration, but it does mean files need to be uploaded or linked manually.
Here are some workarounds you might consider:
1. Attach from OneDrive or SharePoint
- Save the file to OneDrive or the associated SharePoint site for your plan, then attach it to the task using the “Add attachment” option.
2. Use Teams integration
- If your Planner board is in Teams, upload the file to the channel’s Files tab and then link it in the task.
3. Copy file link instead of uploading
- For quick access, copy the file link from Outlook or OneDrive and paste it into the task’s notes or attachment field.
I truly appreciate you sharing your feedback because your issue is thoughtful, practical, and reflects a real need that many users likely share. Ideas like yours help us improve the product in meaningful ways.
I highly encourage you to submit your feedback directly through the Microsoft Teams · Community. Microsoft actively reviews user feedback to guide future updates, and the more input they receive on this topic, the higher the chance it will be prioritized. I will also make a note of your suggestion on my end to help bring attention to it.

As community moderators, we kindly ask for your understanding that our access to internal development details is limited. Our primary role is to guide users toward the appropriate resources and support channels. While we may not have influence product design decisions and have limited access to internal development details, we’ll continue doing our best to support you within the scope of our responsibilities.
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Thank you for your kindness and contributions to the forum.
Sending warm wishes to you and your loved ones for a happy and successful New Year.
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