To reproduce:
Add a RadGridView wth a few columns ,add rows as a few rows should have increasingly long text. Right click on the header cell to show the context menu and click bestfit. You will notice that the size of the column is not correct

Workaround: void grid_MouseMove(object sender, MouseEventArgs e) { this.mouseLocation = e.Location; } private Point mouseLocation; private GridViewColumn currentColumn; void grid_ContextMenuOpening(object sender, ContextMenuOpeningEventArgs e) { if (this.grid.CurrentRow is GridViewHierarchyRowInfo) { RadItem bestFitItem = e.ContextMenu.Items.FirstOrDefault(x => x.Text == "Best Fit"); if (bestFitItem != null) { e.ContextMenu.Items.Remove(bestFitItem); } RadMenuItem newBestFitItem = new RadMenuItem { Text = "Best Fit" }; this.currentColumn = (this.grid.ElementTree.GetElementAtPoint(this.mouseLocation) as GridCellElement).ColumnInfo; newBestFitItem.Click += newBestFitItem_Click; e.ContextMenu.Items.Add(newBestFitItem); } } void newBestFitItem_Click(object sender, EventArgs e) { int highestWidth = this.GetHeightestWidthFromColumn(this.currentColumn); this.currentColumn.Width = highestWidth; } private int GetHeightestWidthFromColumn(GridViewColumn gridViewColumn) { int max = int.MinValue; Font cellFont = this.grid.TableElement.VisualRows[0].VisualCells[0].Font; for (int i = 0; i < this.grid.Rows.Count; i++) { int textWidth = TextRenderer.MeasureText(this.grid.Rows[i].Cells[gridViewColumn.Index].Value + "", cellFont).Width; if (max < textWidth) { max = textWidth; } } return max; }