Although the import of shp filesshapefiles into SQL serverServer can be frustrating, there are two simple processes that can be used assuming you have the shp2sql application.
- Purchase ArcMap for Desktop which cost around $100US per licence per annum. Load the shapefile (eg roads.shp) into ArcmapArcMap 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.
 - 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.