Dear @Keegan Miller,
Welcome to the Q&A Community.
Thank you for sharing your concerns. Unfortunately, Microsoft Planner does not currently offer advanced print settings or scaling options like Microsoft Project does. The "Export to PDF" feature in Planner is limited and does not support full-sheet timeline printing or layout customization.
As a workaround, you can take a high-resolution screenshot of the timeline view and paste it into a Word or PowerPoint document. From there, use the Print > Scale to Fit options to print it on a single page.
If your organization has access to Microsoft Project for the web, you might consider using it for more advanced printing needs. Its Timeline (Gantt) view supports features like scaling to one page, layout orientation, and detailed print settings. You can refer to this guide for more information: Print the timeline in Project - Microsoft Support
I understand this limitation may disrupt your workflow, and I truly appreciate your patience. While we as community moderators don’t influence product design, your feedback is incredibly valuable. I encourage you to submit your suggestions directly through the Planner feedback, where user input helps shape future updates.
In the top-right corner, click on the question mark (?) or feedback icon > Select “Give a compliment” > Fill out the form with your comments, suggestions > Click Submit.
Your feedback is valuable and contributes to the ongoing improvement of Microsoft 365 products. If there’s anything else I can assist you with, please don’t hesitate to let me know.
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