I cut the tails first, mark the pins with a knife and then cut inside the knife line. When I cut my first drawers, it took me hours to cut a single drawer. The more tails / pins in a single cut, the harder it is.
I am working on a case in African Mahogany with 10 tails / 11 pins. I am always a bit concerned when I cut this many. I had a little time to cut the last set of pins on my case, so this is what I had after sawing, no fitting.
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I took a few minutes to do a wee bit of tweeking, and then I had this:
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I then pulled it from my Moxon vise, pared to the base-line, and with a bit of persuasion, I got this:
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It seems that persistence pays off. I spent a lot of time working on my cuts and I have done many dovetails by hand. Very happy with that joint. And now I need to create the drawers.
Of course, idiot that I am, when I cut my first board, I but the tails in the wrong board, but for this application, I think it won't matter. First time I made that mistake. I prefer to have the pins on the horizontal so that the shape will hold things together. I did not have a lot of extra mahogany sitting around to just grab another board....