When do you have to turn your headlights on in Ontario?
From a half-hour before sunset to a half-hour after sunrise, and in poor light
Headlights must be on between one-half hour before sunset and one-half hour after sunrise, and any other time of poor light (fog, snow or rain) when you cannot clearly see people or vehicles less than 150 metres away.
Why the other answers are wrong
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Only once it is completely dark outside
You would be turning them on too late. The clock starts a half-hour before sunset, while it is still light out, because headlights also make you visible to others, not only help you see.
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Only on highways at night
The lighting rules cover every road, city streets included, and the handbook says they apply to all roads, divided ones too. Judge by the time of day and by how far ahead you can clearly see.
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Only when other drivers flash their lights at you
A flash is a courtesy from another driver, not the rule, and by then you are already late. Your two triggers are the clock and whether you can see clearly.
Quick way to remember
It starts before it is even fully dark.
Based on the official Ontario MTO Driver's Handbook.
Reading it once is not enough
Drill this question in a scored round and find out what else you are shaky on.
Practise Rules of the Road: The Basics