How much damage from walking on shingle roof in cold weather?
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Try to minimize how much walking you do on your roof. Walking on a roof when the shingles are brittle (in cold weather) or soft (in hot weather) can damage the shingles. If you have to walk on the roof to take care of a problem, try to do it at the most mild time of day – in the morning in the summer and the afternoon in the winter. Don’t use a pressure washer. A pressure washer will loosen the granules embedded in the asphalt shingles and expose the asphalt to UV rays which will shorten its lifespan. Only professionals should use a pressure washer to clean the roof.
As William said, cold shingles can be brittle but shingles in 50 degree weather should be fine. The more important part is how you step. Walk straight without pivoting on your sole. Pivoting action can pull the chips off the shingle and cause a laminated part to tear loose. Think of the Kung Fu rice paper challenge. Grasshopper needs to walk across the rice paper without tearing it. https://www.google.com/search?q=grasshopper+in+rice+paper&ie=utf-8&oe=utf-8
Your roof is much stronger than rice paper so just basic caution should be fine.
A roofer can do this task for you. They routinely need to blow debris off roofs. AND, their employees are properly insured in case they fall. Roofers have 5 times the on-the-job death rate as police officers.
Personally, I don't get too concerned as long as I step carefully. There are natural events that are harder on a roof than walking on it. Hail ruined my roof. High winds left lots of laminated tabs from my roof on the front lawn. I've had to go up on my roof many times to glue down flapping tabs that never self laminated properly.
I am assuming the roof is a low pitch or there is a LOT of debris on the roof. I find a few good blows from fronts coming through cleans off the roof. Then I do a final gutter clean for the season on a mild windless day..