My left support on my replica TRD wing from chrisc somehow fills up with water, I'm assuming from the two upper bolt holes where the side attaches to the flat wing. It gets so filled that you can hear water sloshing around when you open the trunk. Once water is in there, it slowly leaks through the bottom into my trunk.

I'm considering unbolting the bolts and applying some silicone, then bolting it back together and applying more silicone to get it to not leak, but I'm not sure if this is the best way of doing this.

Does anyone else's replica wing from chrisc do this? Does anyone have any solutions?

sorry to hear this...I have never heard of Manny's chrisc TRD wing doing this

your solution is probably the best/only way
1 unbolt the entire wing
2 get water out
3 dry it up
4 silicone the wing insert and the posts
5 do both sides to be safe

i wonder if his spoiler blocks do the same? any way in checking?

mine doesnt do that. i also got my wing from chrisc

chris, i havent had this problem with my wing from chris.
id do what dustin is suggesting.

I did that the other day and now the leak seems to have stopped.