To reproduce: use the following code snippet. You will notice that the "Accounting Manager" group is missing.

private void Form1_Load(object sender, EventArgs e)
{ 
    this.customersTableAdapter.Fill(this.nwindDataSet.Customers);

    this.radGridView1.DataSource = this.customersBindingSource;

    ColumnGroupsViewDefinition view = new ColumnGroupsViewDefinition();
    view.ColumnGroups.Add(new GridViewColumnGroup("Customer Contact"));
    view.ColumnGroups.Add(new GridViewColumnGroup("Details"));
    view.ColumnGroups[1].Groups.Add(new GridViewColumnGroup("Address"));
    view.ColumnGroups[1].Groups.Add(new GridViewColumnGroup("Contact"));
    view.ColumnGroups[0].Rows.Add(new GridViewColumnGroupRow());
    view.ColumnGroups[0].Rows[0].ColumnNames.Add("CompanyName");
    view.ColumnGroups[0].Rows[0].ColumnNames.Add("ContactName");
    view.ColumnGroups[0].Rows[0].ColumnNames.Add("ContactTitle");
    view.ColumnGroups[1].Groups[0].Rows.Add(new GridViewColumnGroupRow());
    view.ColumnGroups[1].Groups[0].Rows[0].ColumnNames.Add("Address");
    view.ColumnGroups[1].Groups[0].Rows[0].ColumnNames.Add("City");
    view.ColumnGroups[1].Groups[0].Rows[0].ColumnNames.Add("Country");
    view.ColumnGroups[1].Groups[1].Rows.Add(new GridViewColumnGroupRow());
    view.ColumnGroups[1].Groups[1].Rows[0].ColumnNames.Add("Phone");
    view.ColumnGroups[1].Groups[1].Rows[0].ColumnNames.Add("Fax");
    radGridView1.ViewDefinition = view;

    GroupDescriptor descriptor = new GroupDescriptor();
    descriptor.GroupNames.Add("ContactTitle", ListSortDirection.Ascending);
    this.radGridView1.GroupDescriptors.Add(descriptor);

    this.radGridView1.Groups[0].GroupRow.IsPinned = true;
}