using System;

using System.Collections.Generic;

using System.IO;

using System.Linq;

public class Program

{

    private static List<(MyEnum type, string somePath)> myList1 = new List<(MyEnum type, string somePath)>

    {

        (MyEnum.Some, "/Images"),

        (MyEnum.Values, "/Images/Path"),

    };

    private static List<(MyEnum type, string somePath)> myList2 = new List<(MyEnum type, string somePath)>

    {

        (MyEnum.Values, "/Images/Path"),

        (MyEnum.Some, "/Images"),

    };

    public static void Main()

    {

        var myPath = "some/path/to/Images/Path"; // has /Images/Path - which maps to "Values" in the above tuple listings

        var result1 = myList1.FirstOrDefault(m => myPath.Contains(m.somePath)); // we're going to get MyEnum.Some because it's first in the list

        var result2 = myList2.FirstOrDefault(m => myPath.Contains(m.somePath)); // we're going to get MyEnum.Values because it's first in the list

        Console.WriteLine("Expecting enum of type MyEnum.Values: " + result1.type);

        Console.WriteLine("Expecting enum of type MyEnum.Values: " + result2.type);

    }

    enum MyEnum {

        Some,

        Values

    }

}

​