Here are the common issues that can prevent your Surface Pen from taking a screenshot on your Surface Pro. That includes:
You didn’t pair the Surface Pen to your Surface Pro – To fully utilize the full functionalities of a Surface Pen, especially the tail eraser, you will need to pair the pen to your Surface. For detailed instructions, check our article about how to pair or connect a Surface Pen.
Bluetooth is off – Bluetooth is the wireless signal that Surface Pen and Surface Pro use to communicate and perform activation tasks for the tail eraser button and exchange information. To fix this issue, check if your Surface Pro has Bluetooth turned on.
Surface Pen has a low battery – When the single AAAA battery inside the pen gets low, it will occasionally cause the Surface Pen to lose its functionalities. Check your Surface Pen battery status and replace it if too low.