Question
How can we automatically toggle Dark Mode at predetermined times?
Background
Every day, around 5 PM, I switch on the dark mode of the Dark Reader Chrome extension.
I toggle it off again the next morning to get more bright light in the morning.
As of now, I have remind myself everyday to hit the <Alt>+<Shift>+<D>
-shortcut that I have configured in Google Chrome (chrome://extensions/shortcuts):

Nowadays, toggling can be done through the new dark reader-plugin UI.
UI-based automation
As of writing, the plugin has 2 types of interfaces:
- If you see the imaged interface below, you are on the old interface and you need to enable the new UI first. Start at section
Part 1: Enable the new interface
.
- If you see an other UI, you can skip to the
Part 2: Automate the UI
section of this answer.

Part 1: Enable the new interface
Steps:
- Click on 'dev tools' (as shown above). This will open a small window.
- Click on 'preview new design' (as shown below). Note that as of writing, the UI of the small window doesn't visually change. Only the label of the button will change. However, when you click on the plugin icon again, you'll see the new UI.

Part 2: Automate the UI
Steps:
- In the new interface, click on 'settings':

- Then click on 'automation':

- Enable the ✔️ checkmark for the active times. In the example below, the browser will turn dark at 17:00 and bright at 05:00.
