Shingling over a Gambrel Shed Roof?

Hello,
I want to re-shingle my barn (small, 10x8) with a gambrel roof. However, when the former owner had it done, the portion of the roof where the shingles overlapped the "gambrel" part, he taked them down with big staples, as opped to using nails, which rusted pretty quickly.
What I am wondering, is there any best way of tacking down the shingles that go up and over the angle where the two portions of the gambrel roof meet? It doesn't seem like there is really any good way...
Thanks...
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A good warm day, pliant shingles, some roof cement on the lower portion, lots of nails on the upper portion and do you think a second starter course to cover those nails might work?
It is either that or flashing.
Colbyt
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Colbyt wrote:

At this point, I am going to down the flashing road. Also, A lot of cement to hold down the edges of the upper shingle.
Thanks for your input
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Blackadder III wrote:

i would use the sticky rubber membrame, espically if the roof is chip board.
chip board disengrates if wet
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