Since water runs downward unless it s being driven by strong winds the standard method for creating water resistant vinyl cladding is to start at the bottom and work up.
How to seal siding from water.
Use a caulking gun to apply a continuous bead of silicone sealant along the vertical seams between the vinyl j channels and the exterior window casings.
Using a standard sized roller instead of a short roller speeds the process of applying the sealer.
After the paint dries apply caulk and then paint the rest of the siding.
Cover it with a tarp to keep it from sustaining sun or water.
Lay the siding out on sawhorses or on a horizontal surface to make applying the sealer easier.
The temperature should be be no colder.
Check to be sure weep holes are open along bottom of window openings.
Butt the siding next to each other so you can cover more than one piece of siding at a time with the sealer.
If you prefer to caulk before painting you should still paint the cut ends first.
Choose a calm temperate day to seal wood.
Inspect the area above the leak including both indoors and out.