Steps to reproduce:
Install Dark Reader extension > turn macOS's dark mode on/off ≥ page's theme doesn't change with it, as well as the extension icon on the toolbar.
Only when quitting and restarting Orion it "picks up" the correct system theme.
With Dark Reader installed and automatic dark mode enabled, the webpages should change theme automatically depending on whether macOS's night mode is toggled on and off
Orion and macOS:
Orion 0.99.108-beta. macOS Big Sur & Monterey
Bonus bug captured on video: sometimes the extension options don't open when clicking on its icon