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can I use the verb " enter " when I want to talk about people driving into a city ? you can send people automated messages as soon as they enter the city.

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Yes, you can "enter" a city, but you can do so on foot, by train, by plane, in a car, on a horse, etc. "Enter" is not limited to a specific mode of transportation.

If you want to talk specifically about people driving as they enter the city, then use "drive into".

They drove into the city at night, the front windshield ablaze with bright lights and empty promises.

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