To reproduce: public Form1() { InitializeComponent(); List<string> items = new List<string>(); StringBuilder sb; for (int i = 0; i < 10; i++) { sb = new StringBuilder(); for (int j = 0; j < 5; j++) { sb.Append(i + "." + j + ".some text"); } sb.Append(" END"); items.Add(sb.ToString()); } this.radCheckedListBox1.AllowArbitraryItemWidth = true; this.radCheckedListBox1.DataSource = items; } Workaround: measure the desired size for the longest string in the DataSource collection, e.g. by using TextRenderer.MeasureText method, and set the RadCheckedListBox.ItemSize property considering the check-box size as well.