Tips and Tools for Painting Exterior Trim From a Steep Rooftop

Updated on July 14, 2020
Matt G. profile image

Matt is a professional painter and freelance writer, sharing his knowledge, house-painting tips, and product reviews.

The Challenges of Exterior Painting

Painting the trim and siding on a large house comes with various obstacles and challenges. Dormers and walls high above a rooftop are very difficult to paint from a ladder alone. The only way to get close enough to paint these tricky areas is to walk the rooftop. But when a roof's really steep, what do you do?

I've painted and stained dozens of dormers, working on steep rooftops at extreme heights. Painting from a roof is dangerous no matter what, but the right setup and tools will make your project a lot easier and safer.

In this article, I share some tips on how I paint siding and trim from steep rooftops, as well as the essential tools I personally use for these challenging projects.

Fasten Toe Boards to the Roof

The only way to access and paint walls above a steep roof is to fasten toe boards, or roof jacks, to the rooftop. Toe boards are pieces of wood, typically 2x4 boards, that are nailed into the roof for footing and stability when climbing up and down.

Space the boards two to three feet apart leading to the wall you're painting. The first toe board should be placed close to your ladder so you can step on and off the roof without over-stepping.

Lift up the shingles and nail the boards in underneath instead of through the top of them. Shingles with adhesive underneath cannot be lifted up though, in which case the nails must be hammered through the top. Always fill the holes with high grade roofing cement upon removal of the boards. The holes won't leak as long as you completely fill them with the right material. Most home improvement stores sell tubes of roofing repair caulking. Never use regular painter's caulk to fill nail holes in a roof.

My Pivit ladder leveler and Roof Boot for securing ladders and the Pivit on roofs.
My Pivit ladder leveler and Roof Boot for securing ladders and the Pivit on roofs.

Pivit Leveler Tool and Roof Boot

When you're painting from a rooftop you need a level platform to set down your paint can and tools so they don't go sliding down the roof. My long time favorite multi-tool for rooftop painting is the Pivit ladder leveler. The Pivit is a very versatile tool you can use in several different ways for both interior and exterior painting.

On roofs, I use this tool as a stable platform to hold my paint can and caulk gun. The Pivit is an awesome extension ladder leveler for rooftops and staircases. You can also use it to set up a plank, or use it with the Roof Boot.

The footing on the Pivit is covered with anti-slip material for grip and stabilization. I've used this tool over and over again on many steep rooftops without any issues. On roofs with a very steep pitch, I place it in front of a toe board, or the Roof Boot, to be safe. If you're using the Pivit underneath an extension ladder on a roof, you definitely need to secure it with the Roof Boot.

The Roof Boot

The Roof Boot is essential if you plan to erect an extension ladder on a rooftop, using the Pivit, or if you want to lay a ladder down on the roof for climbing up and down instead of nailing in multiple toe boards.

The front of the Pivit tool fits perfectly into the opening of the Roof Boot to totally secure it and prevent it from sliding down. Both tools are made by the same company. I use both tools together to level a ladder on a roof to reach high walls.

The Wagner Paint Eater.
The Wagner Paint Eater.

Surface Preparation for Walls on a Roof

In order to access the trim and siding for prep work and painting, you'll have to either set up toe boards, roof jacks, or lay down and secure a section of an extension ladder with the Roof Boot, as I explained earlier in this article. Nail in your toe boards with enough distance from the siding so that running water from power washing doesn't flow underneath the boards and leak into the roof.

Power Wash

Give the siding and trim a good power washing with a cleaning agent like Jomax to remove dirt and mildew stains. Power washing quickly removes peeling paint too for less scraping and sanding. A gas powered washer with at least 3,000 PSI and 2.5 to 3 gallons per minute is ideal for fast and efficient cleaning. A hose length of twenty five feet is good, but fifty feet is even better for more reach. The gas power washer I use for exterior paint preparation is the Simpson MegaShot.

Scrape and Sand Peeling Paint

After power washing, scrape and sand any remaining loose layers of paint, or stain. The best and fastest way to remove peeling paint is with an electric sander, or paint remover, like the Wagner Paint Eater, which is what I use on peeling siding.

To sand and scrape areas out of reach while standing, you'll have to set up an extension ladder using the two tools that I explained and recommended earlier in this article.

Use Bucket Hooks

Bucket hooks are really helpful when working off extension ladders and for climbing on and off roofs. Clip your paint can to the ladder rung while you step off the ladder onto the roof instead of holding the can in your hand. This allows you to use both hands.

Clip one onto an empty five gallon bucket and use that to store tools at the top of the ladder. Bucket hooks are essential when painting from an extension ladder. Holding a paint can in your hand the whole time is tiring and dangerous if you drop it. The hooks I use have lasted many years. I've never had one break.

Painting High Walls and Trim Over a Roof

Some dormers, chimneys and exterior walls on roofs are higher and unreachable while standing on a rooftop. High walls and trim require extension ladders and leveling equipment to reach them for painting, but for only having to reach a small area of trim, or a few siding boards, brush extenders are the best solution.

Use a Paint Brush Extender

A much safer and easier alternative to setting up an extension ladder on a rooftop to reach upper sections of high walls and trim is to use an extension pole equipped with a brush extender. An extension pole that extends eight feet is perfect in most cases. Longer poles are heavy and more difficult to work with.

The best tool that I use a lot to cut-in out of reach fascia, soffit and siding boards is the Goose Neck brush extender. I use this tool a lot for both interior and exterior painting. The paint brush itself screws onto an extension pole and includes a bendable neck for precise angling. The bristles are very flexible and work great for cutting-in fascia board beneath gutters.

Use Mini Rollers

Mini rollers of 4-inches are awesome for working paint, or stain, into tight corners where boards meet and for painting soffits. I really like the jumbo Contractor Series rollers from Sherwin Williams. Wider rollers of six to nine inches are best for painting siding, but the smaller mini rollers are easier to control in tight spaces.

Use an Airless Sprayer

Airless sprayers are very useful for painting and staining siding. I couldn't imagine doing my siding projects without one. If you're faced with painting siding from a roof, using a good sprayer will get the work done a lot faster. The sooner you finish the painting, the sooner you can get off the roof.

I own both Graco and Titan airless sprayers. For the cost and versatility, if I were to recommend a good sprayer for exterior painting, the Titan 440 Impact is one of the best sprayers to go with. You can spray most exterior paints and stains with the Impact. I use my Impact to spray siding, window shutters, cabinets, interior trim, and walls.

Use a Spray Gun Extension

When painting large areas of siding over a roof, I definitely recommend using an airless sprayer equipped with a spray gun extension. These give you the extra reach you need and you won't have to bend down as much when spraying at certain angles. Spray gun extension poles also put more distance between you and the surface you're spraying, reducing exposure to over-spray.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2020 Matt G.


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