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I've read several some of the guides out there (examples here and here) on this topic. I've found a shingle in the yard a couple times (after heavy wind/rain), and at times I've seen a few granules in the downspouts, but otherwise none of the warning signs are present. My roof is asphalt shingle with age approx. 15 years.

In the St. Louis area where I am, conventional wisdom says that 20 years is as much as you can expect out of an asphalt-shingled roof, so replacement is on the horizon. The best time to replace it, I suppose, would be the day before it starts to leak. Short of using a crystal ball, what other factors would help narrow down the optimal time to replace? I don't want to replace it now if it would still have several years of service left, but don't want to wait until it leaks either.

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I'm not an expert, but if you find shingles in your yard, doesn't that mean there are shingles missing from your roof? Isn't that bad? –  Henry Jackson May 11 '13 at 19:49
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It depends on what your goal is. If the goal is to never have water enter your house in any way then probably what you need to do is get one of the shingles that fell off and see what its lifetime rating is. Most are 15-20 years. If you are near that point and shingles are coming off then I would think about it.

However shingles falling off doesn't necessarily mean you need a new roof. It could have been a bad install on that part of the roof - or everything.

What you read is pretty true though except for the vegetation part. If you have tree coverage over your house you might get moss with a 2 year old roof. The curled, cracked, badly warped shingles... this is extreme and should be replaced.

If you want to wait to the last second, then you need to venture to your attic a lot - after big rains. Most of the time a roof will show signs of moisture before it starts letting in a lot of water - unless your roof is pretty flat. If you don't want to get up in the attic to do this then it is purely a guess/luck.

Last thing... How long do you plan on being in the house? If it is less than 10 years. Do you plan on replacing before reselling? If yes and yes. Then just replace it and enjoy the roof.

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It can also depend on how many layers you have down. Some places will allow up to three although I think two is the law in most places. I've heard roofers tell people on their third layer to wait until the shingles are really coming down since most likely when a shingle falls there will still be one or two underneath. That said it's not a guarantee.

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