An alternative to pipe insulation that will prevent any water from passing
between the shady boy body and rain gutter is the adhesive backed foam
gasket tape.  There is a concave channel on the shady boy that makes room
for the vanagon gutter which is a great surface for sticking the gasket tape
to.  They make the gasket tape in a width that will fit this channel well.

Once you get the gasket tape stuck to the shady boy you reinstall the shady
boy and the vanagon gutter is sealed off against the shady boy's aluminum
body completely.  The tape has minimal contact with the vanagon's paint and
should not block the gutter from draining or encourage rust.

This sounds similar to what was discussed but if the pipe insulation doesn't
block all water from the shadyboy/gutter gap then I'd switch to foam tape.

What I'd like is a comparably easy way to keep rain out of the gaps fore and
aft of the shady boys body.  My sliding door get's wet and rain comes in up
front if the window is open.  Maybe an extension flap that clips on to the
gutter?  Anyone solved this problem?

While I'm at it, a good solution for puddling rainwater would be nice too.
Raising and lowering the outside edge (away from van) has helped me address
this, and running a line accross the three support poles, under the fabric
has helped create another ridge and keep the poles arched up well but still
I get puddles that grow until the awning gets stretched and strained.

I'm currently in a spot where I've had the shady boy up for a few weeks and
I am trying to sort out it's annoyances or let the wind and rain take it
once and for all..

Jonathan Poole