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I have really sensitive eyes (astigmatism, easily strained, dry, photosensitive) and I can't look at a screen without my glasses for more than a minute without getting a headache (but have otherwise perfect vision). The e-ink screens i own, a last gen Kindle and an Onyx Boox, are really paper-like and do not tire my eyes at all.

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I have no idea whether it helps with headaches, but have you considered getting a reflective monitor, e.g. https://www.sunvisiondisplay.com/reflective-lcd-monitor ?

I doubt it, glossy reflective screens really tire my eyes after a prolonged use (like a day of work), unlike matte screens.

Some ideas. Feel free to ignore.

Dry eyes? Maybe Sjogrens.

I spent years barely able to look at a monitor. Turned out my prescription was constantly shifting due to cranial pressure. Medication fixed.

Eventually found out that eye doctors were giving out wrong prescription when using machine. Has to be done by hand. It’s rare, but happens.

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