roof leak

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I must have a small roof leak in my 1.5 story, 2 dormer, roof.
There is a small darkening spot, about 6" in diameter, on our 1st level bathroom. It's about right at the point where the 1.5 story dormer meets the roofline. From that bedroom I looked out onto the roof and see the shingles as they come up to the roof nailed at the very top where the roof meets the dormer. The top row of shingles are nailed and the nails are exposed. One nail in particular seems to have broken through the shingle. I'm thinking I need to start there and somehow seal that nail. How should I do that?
What else do I need to look for? How should the roof shingles as they meet the dormer walls be installed? It just seems like that is a leak waiting to happen with a wall running down to a roof where it cannot be properly capped. Is there some sort of flashing there?
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Here is the house: http://www.dongardner.com/images.aspx?pid 3&fn=exteriors%5c235front1.jpg&f The leak seems to lead up to the roof where that single 2nd level window on the main living area is shown in this picture.
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Flashing is an art form. Slapping some roofing cement on what you're describing is just as likely to trap water and make the leak worse. If you posted some pictures of your house, not the generic house, and the specific location where you are having a problem, you'd get more constructive responses and advice.
R
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Also consider any plumbing vents. Since it's over a bathroom, it could be from a vent if there is one there. The rubber boots fail over time. Why not climb into the attic during a rain and take a look up there?
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I don't think I can very easily get to that location. I have not tried yet, but there is not going to be much, if any, headroom in the attic at that location.
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Your description of the loation of the leak doesn't make any sense. " single 2nd level window on the main living area is shown in this picture". There are 3 windows on the 2nd level on the front and one on the side, assuming that the two-story building in the back is not what you're talking about. If you have to use a generic photo, put an arrow pointing to where the leak is!!!
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It's the side window -- the "single window on the 2nd level".
Below that window is a bay window that is apart of the bath.
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Why not post a thumbnail so we could have an even smaller less detailed picture to guess at?
R
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Agreed, the description from the OP would make more sense if he showed a photo of what he saw when he looked out the window.
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How do I post a photo?
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http://tinyurl.com/yf2r3jl
You can't. Not here, anyway -- this is a text-only newsgroup.
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Post the pictures on a free hosting site like Flickr or TinyPic. Then post the link here with your question.
R
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http://tinypic.com/m/64p9fo/3
Right at the cursor arrow -- along that top row of shingles against the dormer wall, there is a nail in the shingle that pushed through the shingle. About straight below that point -- in the master bath on the 1st floor -- the ceiling is discoloring.
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On Fri, 23 Oct 2009 12:27:34 -0700 (PDT), coloradotrout

For now, tar the nailhead.
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Henry's roofing cement (at home depot) ?
or what's the best?
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On Sat, 24 Oct 2009 13:11:38 -0700 (PDT), coloradotrout

Bulldog WetStick fibrated roofing cement has always worked for me.
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On Oct 24, 10:30pm, snipped-for-privacy@snyder.on.ca wrote:

Which ones haven't?
R
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First, make sure there's some flashing under the siding, and out onto the shingles. Also, check the step flashing going up that wall to the right of the window in the photo. I await your response. Tom
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wrote:

If it didn't leak before the flashing is likely OK. The popped nail is enough to cause a minor leak.
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On Oct 25, 10:52am, snipped-for-privacy@snyder.on.ca wrote:

Any idea how old this roof may be? I saw nothing about that in his decription. Another idea may be an improperly installed bathroom vent exhaust. Tom
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