Steps to reproduce:
1. Add RadGridView and populate with data 
2. Show the context menu many times. Sometimes the popup is not shown correctly.
If you click again, the popup is visible correctly.

Workaround: 
Set the AnimationEnabled property to false or the AnimationType property to None. Here is the code snippet how can be achieve it: 

//Set the AnimationEnabled to false
void radGridView1_ContextMenuOpening(object sender, Telerik.WinControls.UI.ContextMenuOpeningEventArgs e)
{
    RadDropDownMenu contextMenu = e.ContextMenu as RadDropDownMenu;
    contextMenu.AnimationEnabled = false;
}
 
//Set the AnimationType to None
void radGridView1_ContextMenuOpening(object sender, Telerik.WinControls.UI.ContextMenuOpeningEventArgs e)
{
    RadDropDownMenu contextMenu = e.ContextMenu as RadDropDownMenu;
    contextMenu.AnimationType = PopupAnimationTypes.None;
}