Not sure if this is intentional or not; however, given the description is "Try Dark Mode" and not "Set the theme to Dark Mode", I figured I'd bring it up.

At least under Safari 14.0, with the theme set to "System setting" on SO and the system setting set to dark, the hat is not awarded.

[![enter image description here](https://i.stack.imgur.com/vFHql.png)](https://i.stack.imgur.com/vFHql.png)

[![enter image description here](https://i.stack.imgur.com/lFffr.png)](https://i.stack.imgur.com/lFffr.png)