Can't import shapefiles into SQL Server, because of Encoding issues

First you should find out the enconding of your database. This answer should help you find out.

As shape2sql does not have an option for encoding you should encode your shapefile according to your database encoding.

Or you can change the encoding of the database like mentioned in this answer.

If you want to change the encoding of your shapefile there are many ways to do so. You could use QGIS and save your layer with the new encoding. You also can use LibreOffice to save the .dbf in another encoding. The important thing is to have the correct encoding in the programs at first.

I have no idea why importing shape files should be such a twisted, complicated task. I ended up using SharpMap library, using only GeoAPI, NetTopologySuite, ProjNet, and SharpMap DLL files in a console application, to import it via C# code.

For future reference this is my code, and explanations are afterwards:

class Program
{
    static void Main(string[] args)
    {
        args = new string[] { @"D:\Temp\iran-latest-free.shp\gis.osm_places_free_1.shp" };
        EnsureArgs(args);

        Initialize();

        var shapeFile = new ShapeFile(args[0]);
        shapeFile.Open();
        if (shapeFile.GetFeatureCount() == 0)
        {
            throw new FrameworkException("No records found to be imported");
        }
        string tableName = CreateTable(shapeFile);
        InsertRecords(shapeFile, tableName);
    }

    private static void InsertRecords(ShapeFile shapeFile, string tableName)
    {
        var count = shapeFile.GetFeatureCount();
        int counter = 0;
        for (int i = 0; i < count; i++)
        {
            var feature = shapeFile.GetFeature((uint)i);
            var columns = shapeFile.GetFeature((uint)i).Table.Columns;
            var columnsScript = "";
            foreach (DataColumn column in columns)
            {
                columnsScript += "[{0}],".Fill(column.Caption);
            }
            columnsScript = columnsScript.Trim().Trim(',');
            columnsScript += ", [Geo]";
            var valuesScript = "";
            var values = feature.ItemArray.Select(x => x.ToString());
            foreach (var value in values)
            {
                valuesScript += "N'{0}', ".Fill(value.Replace("'", "''"));
            }
            valuesScript = valuesScript.Trim().Trim(',');
            valuesScript += ", geometry::STGeomFromText('{0}', 4326)".Fill(feature.Geometry.AsText());
            var query = @"
                insert into {0} ({1})
                values ({2})
            ".Fill(tableName, columnsScript, valuesScript);
            Database.Open(RepositoryFactory.ConfigurationRepository.Context.Database.Connection.ConnectionString).Run(query);
            Logger.Count(counter++);
        }
    }

    private static string CreateTable(ShapeFile shapeFile)
    {
        var columns = shapeFile.GetFeature(0).Table.Columns;
        var columnsScript = "";
        foreach (DataColumn column in columns)
        {
            columnsScript += "\r\n" + column.Caption + " nvarchar(max),";
        }
        //columnsScript = columnsScript.Trim().Trim(',');
        string tableName = "Temp" + RandomHelper.GenerateAlphanumericToken(10);
        var tableScript = @"
            create table {0}
            (
                {1}
                Geo geometry
            )
        ".Fill(tableName, columnsScript);
        Database.Open(RepositoryFactory.ConfigurationRepository.Context.Database.Connection.ConnectionString).Run(tableScript);
        return tableName;
    }

    private static void Initialize()
    {
        var gss = new NtsGeometryServices();
        var css = new SharpMap.CoordinateSystems.CoordinateSystemServices(
            new CoordinateSystemFactory(),
            new CoordinateTransformationFactory(),
            SharpMap.Converters.WellKnownText.SpatialReference.GetAllReferenceSystems());

        GeoAPI.GeometryServiceProvider.Instance = gss;
        SharpMap.Session.Instance
            .SetGeometryServices(gss)
            .SetCoordinateSystemServices(css)
            .SetCoordinateSystemRepository(css);
    }

    private static void EnsureArgs(string[] args)
    {
        if (args.Length == 0)
        {
            throw new FrameworkException("Arguments are not provided");
        }
        var file = args[0];
        if (!File.Exists(file))
        {
            throw new FrameworkException("File {0} doesn't exist".Fill(file));
        }
    }
}

Disclaimer: This code is done by me, without truly knowing what I'm doing. I just know that GIS is based on data, and I need to insert some data for each point in SQL Server. Database is my own utility wrapping ADO.NET's functionality. Fill is a utility used instead of string.Format. This code might break for you. It's just here to help people like me know more about tools available to them. Also all fields are imported as nvarchar(max) for the least possibility of any data type problems. Table is created on the fly via a RandomHelper class which is also mine, and just creates a random token.

Although the import of shapefiles into SQL Server can be frustrating, there are two simple processes that can be used assuming you have the shp2sql application.

1. Purchase ArcMap for Desktop which cost around $100US per licence per annum. Load the shapefile (eg roads.shp) into ArcMap and then save it as a data export giving it another name such as roadsA.shp, then using shp2sql import the later file into SQL.
2. Using QGIS (free) load the shapefile into QGIS, then using Layer/Save As... Type in a file name that you want to save the original shp to. Make sure your CRS is set to the correct zone. For some reason, I selected latin1 for Encoding. In Layer options select POLYGON as the SHPT type, or other options depending on what the shapefile is - polygon, line, point, etc. Select OK then use the shp2sql application.