Caulking windows to give them a finished look inside and out and seal out leaks and drafts is a fairly common diy task.
How to seal windows with vinyl siding.
But if done incorrectly it can lend a sloppy amateurish look.
This prevents any air leakage.
In this video this old house general contractor tom silva shows how to prevent water from leaking in behind vinyl siding.
Often water leaks at a window result from a breakdown in the connection between the window frame and the wall.
Caulk is used to seal spaces between two objects.
Sealing these spots with caulking is not possible because the siding must expand and contract freely to prevent warping.
Vinyl siding installs in pieces so gaps and overlaps are normal.
Check to be sure weep holes are open along bottom of window openings.
Remove the pieces of vinyl siding from around the window area.
Smooth out the caulk.
In this case the objects are the perimeter of the new exterior wall and the perimeter of the old open space.
If the window is surrounded by wood trim use a high grade polyurethane caulk to seal all gaps between the trim and the siding and the trim and the window.
Caulking can be placed behind the j channel during installation sealing the seam between the j channel and the house wrap also sealing the seam between the j channel and the window itself.
Vinyl siding by itself does not create a waterproof seal and care must be.
Inspect the area above the leak including both indoors and out.