The quick and dirty answer is that [we] discourage it. It's not difficult to understand why dogs might enjoy riding with their heads out the window.
I've seen dogs jump or fall out of the car window in both small and large cases, and it can be fatal.
If you think about rocks or pebbles that will crack your windshield, think about that happening to your dog, which can cause damage.
Letting your dog stick its head out the car window can also create distractions for other drivers.
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