I have
 <DataGridCheckBoxColumn 
     Binding="{Binding Path=Foo, Mode=TwoWay, UpdateSourceTrigger=PropertyChanged}"
 />
And
 public bool Foo{ get; set; }
Checking/Unchecking sets Foo, but setting Foo in code does not change the Checkbox state.  Any Suggesitons?
You need to raise the PropertyChanged event when you set Foo in your DataContext.  Normally, it would look something like:
public class ViewModel : INotifyPropertyChanged
{
    private bool _foo;
    public bool Foo
    {
        get { return _foo; }
        set
        {
            _foo = value;
            OnPropertyChanged("Foo");
        }
    }
    public event PropertyChangedEventHandler PropertyChanged;
    protected void OnPropertyChanged(string propertyName)
    {
        var propertyChanged = PropertyChanged;
        if (propertyChanged != null)
        {
            propertyChanged(this, new PropertyChangedEventArgs(propertyName));
        }
    }
}
If you call Foo = someNewvalue, the PropertyChanged event will be raised and your UI should be updated
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