Tall ceilings and stairwells make painting difficult if you don't have a good level surface for a ladder. You still have several options for applying a new layer of paint; the right one for you depends on your budget and skills. You will need to clean the area before applying paint, or the paint may not stick due to accumulated dust and cobwebs. Use a vacuum with several extension hoses or a duster with an extension pole to prepare your high ceilings for a new coat of paint.
Cover the top of an extension ladder with foam to keep it from marring your walls, and then place the feet on one of your lower stair steps and lean the top of the ladder against the wall so the ladder slants in the opposite direction of your stair rise.
Slide a 2-inch-thick by 10- or 12-inch-wide 8-foot-long plank between your ladder's sides so it rests on one rang. Let the other end rest on a stair step so the board is as close to horizontal as possible.
Stand on this board to paint the ceiling and upper walls, and then shift it down to the lower rungs as you move down your stairwell walls.
Place the board between two A-frame ladders to reach ceiling areas that are not above the stairwell.
Paint your high ceilings and stairwell from the floor if scaffolding isn't an option due to space or budget. Start by taping a paintbrush to an extension pole with duct tape.
Place your paint bucket in a position where you can reach it with the extension pole, such as at the bottom of the stairwell. Dip your brush into the paint, and then apply it to the ceiling by extending the pole as far as necessary. This method offers less control than up-close painting, but gets the job done.
Remove the brush and tape once the edges are painted. Screw a roller frame onto the extension pole's tip using the built-in threads.
Place your roller tray full of paint where you previously had the dipping bucket and apply the paint to your ceiling, using the extended roller. Roll slowly to minimise splatter.
Reduce the pole's length as you work your way down the stairwell walls.