Hello JR JR, welcome to Microsoft Q&A forum.
I understand your frustration. Unfortunately, there's no setting to keep the playlist permanently visible in Windows Media Player. Windows Media Player is legacy software that Microsoft deprecated years ago and no longer actively maintains. Over time, some behaviors may have changed or worsened as the program isn't being updated properly anymore—what you remember working before may have degraded.
You still got some decent options:
- Use the keyboard shortcut: Press Ctrl+M to quickly toggle the playlist on/off when you need it.
- Stay in Library view: Instead of switching to Now Playing mode, stay in the Library view where the playlist remains visible.
- Switch to a different media player: VLC Media Player or MPC-HC have persistent playlist panels that don't auto-hide—they might be a better fit for how you want to use it.
Since WMP is deprecated and actively getting worse over time without support, switching to a modern player like VLC is your best path forward if this is disrupting your workflow.
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