Pre-Assembled Cedar Shingles
It's possible to install cedar shingles with a hammer, and that provides the most control, but with 900 nails per square, the job will go a lot faster if you use a pneumatic nail gun.
The other big advantage to using a nail gun is that you have one hand free to hold the shingle-strip. Fortunately, if you have consistent, regulated pressure from your compressor, most nail guns will do a good job of controlling how far the nail is driven.
Whether you are installing siding or roofing, you should use a coil siding nailer, not a roofing gun. Roofing nails have a wider shaft so will be more likely to crack the shingles. They also have large heads, designed to hold asphalt or composite shingles.
All of the coil siding nail guns that we have used, worked well, and they all use the same nail coils.
A pneumatic medium crown stapler can also be used to install the shingles. Nails are available in longer lengths, which may be necessary if you are installing over rigid insulation. Nails are also available as ring shank nails, which may hold better.
Cutting the shingle-strips with a compact battery powered circular saw (4-1/2 to 5-1/2") is a lot easier than using a larger corded circular saw.
Chalk Line - Align the Shingle-strips to chalk lines, which can be snapped on the felt / WRB above. Since you may also occasionally snap lines on the shingles, use the blue chalk, not the more permanent red chalk.
Hammer & Nail Set - for the final drive on nails that didn't go quite far enough, and for face nailing finishing nails at the top of the wall and below window sills.
Jigsaw - For cutting complex shapes where shingles meet trim.
Screwdriver (small flat) - For prying out the shingle clips to separate the shingle-strips.
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Installation will be faster / easier if you have a table that will support the shingle-strips and enable you to make quick, square cross cuts. See the Instructions for info on how to make a simple saw table, or look online for videos on "cross cut jigs".
See the Fasteners Quantity table to determine how many fasteners you will need.