In SSMS we are attempting to bulk insert from a csv file into a table that has a column encrypted using SQL Server 2016's Always Encrypted feature. This is the command we're using: INSERT INTO membersE SELECT * FROM OPENROWSET( BULK 'c:\members.csv', FORMATFILE = 'c:\membersEFormat.xml', FIRSTROW = 2 ) m This returns the typical error you get when attempting to insert into an encrypted column: >Msg 206, Level 16, State 2, Line 6 Operand type clash: varbinary is incompatible with varchar(50) encrypted with (encryption_type = 'DETERMINISTIC', encryption_algorithm_name = 'AEAD_AES_256_CBC_HMAC_SHA_256', column_encryption_key_name = 'CEK_Auto1', column_encryption_key_database_name = 'DATABASE') collation_name = 'Latin1_General_BIN2' We understand that you can't insert into an encrypted column via SSMS and that you need to use a .NET 4.6.1+ client, but we'd like to know if bulk insert operations are not possible as well? **SAMPLE CODE THAT WORKED FOR ME** (to satisfy Windows10's request) SqlCommand cmd; SqlConnection conn; SqlBulkCopy copy; SqlDataAdapter da; DataTable dt; using (conn = new SqlConnection(ConfigurationManager.ConnectionStrings["Database"].ConnectionString)) { conn.Open(); using (cmd = new SqlCommand("SELECT * FROM members", conn)) using (copy = new SqlBulkCopy(conn)) using (da = new SqlDataAdapter(cmd)) using (dt = new DataTable()) { cmd.CommandTimeout = 600; da.Fill(dt); cmd.CommandText = "TRUNCATE TABLE membersE"; cmd.ExecuteNonQuery(); copy.DestinationTableName = "membersE"; copy.WriteToServer(dt); } } }