(Answering from a Silverlight perspective so assuming this will help you.)
Are you doing a RedoCommand.RaiseCanExecuteChanged()
anywhere? Once whatever condition you are monitoring changes, you'll need to raise this command manually.
EDIT
Since you are using MVVM Light.. Heres sample code:
RedoCommand = new RelayCommand(undoRedoController.Redo,undoRedoController.CanRedo);
public bool CanRedo()
{
redoStack.Count();
redoStack.Any();
return redoStack.Any();
}
public void Redo()
{
if (redoStack.Count() <= 0) throw new InvalidOperationException();
IUndoRedoCommand command = redoStack.Pop();
undoStack.Push(command);
command.Execute();
// At this point, your stacks have changed; that is, the stacks
// may or may not contain items. Thus, raise the commands CanExecute part
// which will in turn enable/disable the commands based on the functions
// return value
RedoCommand.RaiseCanExecuteChanged();
// assuming you could possibly have an UndoCommand somewhere
UndoCommand.RaiseCanExecuteChanged();
}