Would it be possible to remove the shutters/false window and apply 2 layers of Tyvek under it? The first would go all the way to the bottom edge of the garage. The second would go down and overlap a piece of flashing like kwikfishron mentioned yesterday. This assumes that there is just OSB behind the window feature and not a hole for a window. The first layer would protect the siding down to the garage side. The second would cover the water getting passed the shutters and dump it to the outside of the siding as shown.
I've no experience with this myself, so this is just an observation and suggestion looking at the situation.