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I'm not sure what verb to use to refer to people who are crossing the limits of a city entering it. consider this example:

"I want to send an automated message to all the drivers crossing my city border, entering it."

is it correct to use the word, enter here?

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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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