While my backyard, normally, has little draft/breeze when the rain arrives all bets are off. I've seen rain blow in both directions in the same storm. I will say, however,
- the shockcord was probably not tensioned properly
- the foot-end was not staked
- And for that matter I was not present and I had not weighted my bedding with my pack
So it's all on me. That was 2-3 hours ago. I've taken apart my bivy, mattress and two pillows hoping they will dry but not too confident based on the overall humidity.
As for the pillows. They suck! Both of them. The synthetic pillow absorbed water and leaks water every time I squeeze. The air pillow has a soft coating that has simply absorbed some water and is also not dry yet.
I think the primary pillow needs to be an air pillow with no coating at all. Then use a scarf, neck gator, micro towel or schmogg(sp). The microfiber coated pillow is a close second.
One thing I need to keep in mind is that if I'm in the shelter and the weather turns foul then everything is getting wet and I would need to find a way to embrace the rain or lower the tarp. The tarp pictured above is only 9' and that leaves barely 1 1/2' at the head and foot ends.