1. Worn out seal on your step flashing
Step flashing are thin pieces of metal with a 90 degree angle. They are installed one at a time and are placed on the unexposed portion of the shingle while the other surfaced is placed flush with the vertical surface. It is recommended before installing to widen the it out so that it is more like a 110-120 degree angle rather than 90 then press it to the vertical surface till it fits firm then put 2 fasteners in it make sure that part placed on the roof are installed under shingles and on the joints of your roof in order to create a water-resistant barrier, If installed properly there should be no need for any type of caulking. When installing around a chimney it is recommended to use a counter flashing.This is common when shingling over an existing roof because the old roof wasn't removed they were unable to install new flashing. Another reason is that when you had the roof replaced last time the roofing contractor cut corners and left your old flashing on instead of replacing it.
2. You Have Broken or Missing Shingles
This is very obvious and easy to spot after a heavy storm it is recommended that you walk around your home or property and examine the roof. Shingles are made so that the part of the shingle that is supposed to be exposed and the part of the shingle that is supposed to be covered are different shades and colors. Another sign that you have missing or broken off shingles is finding them in your yard or driveway. If you live in an area where heavy winds are common it is recommended that you go with shingles especial engineered to withstand that type of weather. Like CertainTeed's high impact asphalt shingle Solaris not only do the have a high wind rating the also have a good reflective quality that will help keep your roof cooler and therefore help to keep cooling cost down.3. You Have Ice Dam Buildup
Ice dams form mainly on the eaves as water from the roofs melts and runs down to the eaves it is blocked from from draining. Night falls and the water chills and makes the ice dam even bigger. then the next day more snow melts and runs down it pools behind the ice and starts to work its way under the shingles now the water is traveling up the roof. Shingles are designed to stop water that run downward not upwardThe area of the roof that is within the exterior wall of the building gets heated from blow the eves of your home are a lot cooler therefor the freeze and cause ice build-up. In the illustration above you can see how the water can actually get under the shingle and travel up-ward that why it is important to have ice and water shield placed high enough on the roof to stop water from getting inside your home after it gets behind the shingles. In most areas ice and water has to extend minimum of 2 feet inward from the outer wall of the home in very cold areas like cities in mountainous areas having the whole roof covered with ice and water shield is required.
To prevent ice dams heating cable can be installed on your roof.
4. Your vents need replacing
A lot of times in order to cut down on expenses the vents are not replaced when the house is re roofed and. If you have metal vents they on your roof you should be able to get away with not replacing but if they are made with plastic just replace them. Another reason why vents will leak is because of improper installation.
5. Your pipe boots are worn out or need to be re-caulked
Like the air vents sometimes people don't replace the pipe boots. However if you have the type of pipe boot that has a rubber seal these should always be replaced the other type of boot is an all metal boot these have to be caulked with an asphalt base sealant. Asphalt caulking or sealant generally last about 15 years. The other problem is when the boot is installed wrong. What they have done is installed the roof then placed the pipe flashing down on top of it. The only shingles that should be installed under this flashing is one and a half rows the rest should be installed over then caulked all the base of the flashing to prevent it from running underneath the shingles as an added measure.
6. Your Skylights Were Improperly Installed
Skylights are a place on the roof where snow will pile up so they have to be properly flashed and counter flashed or they will leak every time. it is also generally not advisable to place skylights neara valley (another place snow tends to build up).
7. Your Gutters need cleaning or the down spouts are clogged
When your gutters or downspouts are clogged water can penetrate via your fascia board if you have trees around your property i recommend cleaning or having someone do this for you every fall after the leaves have dropped. If your down spout gets clogged try running a garden hose on the top and if this doesn't work call in a rain gutter specialist. rain gutters are a very important part of protecting your home if they can channel the water away from your home properly it can lead to foundation damage as well damage to your fascia board.
8. Improperly flashed or cracked chimney
If you have a cracked chimney crown there is a crown coating materials such as Chimney Saver Crown Coat which cover the masonry and prevent small cracks from becoming a real problem. Below is an illustration of a chimney located at the bottom of a valley. For obvious reasons this is not a good ideaunfortunately sometimes this is how the house was built. In this
circumstance I would either put heating cable or build the roof out more so that the valley comes out on the other side of the chimney however if you build the roof out more it would be a lower pitch so heating cable may still be recommended.
9. Improperly installed or poorly placed valley
The picture above that I used to demonstrate chimney issues is also a good example of a poorly placed valley. The illustration below shows a similarly poorly paced valley that is clogged as well.
When installing valleys the main problem is that the rows of shingles start dropping. The reason it happens is because the shingle has to be placed so that the valley line is in the center of the shingle.
So the start by making a rake right up the valley. A better way is to make 3 rows while doing this so that you can see that it is running straight. An even better way is to chalk lines however this takes more time. When the rows start dropping usually what happens is the roofer will try and straighten them out be compensating and running the the rows above a little high eventually getting them back to straight however because this is a valley where water and snow from two roof surfaces meet its not a good practice to make corrections like this. Is better to just remove the shingles and start over but how often do you think a roofer will do this.