I like tails first. Steven Newman does well as a pins first guy though. Like anything, it’s all in what works for the hands doing the work.

Historically, many old-time woodworkers made dovetail joints by cutting the tails first. While both "tails-first" and "pins-first" methods have been used for centuries, cutting the tails first is widely regarded as the traditional approach in many regions, particularly for ensuring high-quality joinery.

Why Old-Time Woodworkers Cut Tails First

Easier Marking: Cutting the tails first allows the woodworker to lay the "tail board" flat on top of the "pin board," making it straightforward to trace the exact shape of the tails onto the end grain of the second board with a knife.

Consistency (Gang Cutting): Traditionally, craftsmen would clamp the two side boards of a drawer or box together and cut the tails for both sides simultaneously. This guaranteed that the tails matched perfectly on both sides.

Easier Sawing: Cutting the angled lines of the tails first can be easier than starting with the straight, yet more finicky, perpendicular cuts required for pins.

Superior Accuracy: Many old-time woodworkers believed that tails-first made it easier to get a pristine, tight fit, as they could cut the pins slightly over-sized and fit them to the tails.

Hope this helps everyone! 😉

Cheers!

MrRick

So..when I made those 3 drawers for the current project....and found not being able to use the right thumb....we have ways..

Router table, adjust the fence..

Sockets were cut (Pins first?)

Working towards the center...

Trace around these "Pins"..

And because I always use the bandsaw to remove waste between the tails..

Note: In building drawers, make sure a tail covers the grooves for the drawer bottom..

Reason: I can SEE a lot better as to where I am sawing, cuts are square face to face..and, I usually try to leave the lines, and cut only on the waste side...

Part of the groove is a bit deeper...needed that mallet to dry fit right off the bandsaw..

Second end, dry fitted only with the drawer back in the dados..

YMMV, of course...

Watched a you tube vid, last night...Jim Kingshott does dovetails.....a little too old school for me...

just as an aside a number of years ago, the ww club had a guest speaker who manufactured a dovetail jig. It seemed nice in that it could cut thru dovetails (not half-blind), and had a couple of different spacings. Sadly I bought one. A month or so later, he came back and offered a class in using it. When I then got it into my shop, I spent nearly a whole weekend studying it, making notes, drawings, etc. I was fairly complicated to set up in that it would only cut 2 or 3 joints at a time, then you needed to move the stop block and on to the next. (My take on this is any time you move something, it allows a chance for an error). Well, I made a few things, but haven't gone back for several years.

Then I got a "top tip of the month" from a submission to Wood Magazine. The prize was a router table (and I already have two) and a nice dovetail jig, that I've never used.

Another :" top tip of the month" that I submitted was a shop made jig for doing box joints that eliminates any need for fine tuning and even allows various widths of the pins. That prize was a moisture meter, likewise never used.

2 minutes ago, kmealy said:

I made a few things, but haven't gone back for several years.

Sold my 50 pound Porter-Cable Omni-jig for similar reasons.

What a bummer!

On 4/21/2026 at 10:08 AM, MrRick said:

@kmealy did it look like this?

Worse than that, all the tapers were in the wrong direction (narrow edges to the distal side)

Paul... my favorite guy.

One of my favorite Dovetail Jigs is the Keller. I have one, been a long time since I used it, but I loved it. My dad bought in the early 90's for box joints to build his bee hives, he then gave it to me after he decided buying the hives was more cost efficient.

I made some pretty nice things with that old Keller, I still have it today. It doesn't get much more simpler than the Keller, IMHO.

Here is the exact one I have. It takes some initial set up and dialing in with your own home made backstop, but once ya get it right, it does one thing great, and that's making through DT's.

I made two blanket chests using my Keller among other items, such as drawers and more. 🙃

Beautiful Blanket chest John! I had several router jigs for dovetails. I gave them away. I learned to cut all my dovetails by hand with backsaws and chisels. There's no turning back for me. I enjoy it too much.

17 minutes ago, MrRick said:

There's no turning back for me. I enjoy it too much.

Thanks for the kudos Rick, and ya, I'm getting there now, my last attempt yesterday was a bit better, doing them by hand is very satisfying that's for sure.

They look great John, amazing what a difference the poplar makes, isn't it?

Mahogany is a good one for this too, saws and pares very easily.

I briefly posted on reddit for a while, until I got tired of all the kids who knew everything. I used to try to tell them all sorts of things they didn't want to hear, like that the sloppiest dovetail is still a very strong and functional joint.

I did tails first initially, and then realized how hard it was to transfer super slim pins if you did the tails first. Now I do pins first. But it doesn't really matter, whichever works best for you is the one to use (kind of like sharpening, and any other subject that causes a knock down drag out battle on woodworking forums! 😀)

14 hours ago, JWD said:

They look great John, amazing what a difference the poplar makes, isn't it?

Mahogany is a good one for this too, saws and pares very easily.

Thanks JWD and you bet, the poplar was a major difference in workability and sharp edges. Mahogany makes total sense, with the even and consistent grain and molecular structure of the species, I haven't worked with Mahogany in years, I'd love to get something going with it.

14 hours ago, JWD said:

I briefly posted on reddit for a while, until I got tired of all the kids who knew everything. I used to try to tell them all sorts of things they didn't want to hear, like that the sloppiest dovetail is still a very strong and functional joint.

I agree JWD.

14 hours ago, JWD said:

I did tails first initially, and then realized how hard it was to transfer super slim pins if you did the tails first. Now I do pins first. But it doesn't really matter, whichever works best for you is the one to use (kind of like sharpening, and any other subject that causes a knock down drag out battle on woodworking forums! 😀)

Aww yes, the debate is never settled for this touchy subject, it can almost seem like a taboo to discuss right, like politics and religion. 😆 I'm going to try pins first eventually, sooner than later actually, I have to so I can be educated on my debates! 😁

41 minutes ago, John Morris said:

Aww yes, the debate is never settled for this touchy subject, it can almost seem like a taboo to discuss right, like politics and religion. 😆 I'm going to try pins first eventually, sooner than later actually, I have to so I can be educated on my debates! 😁

As Rick points out, tails first is useful for gang cutting, so it's always good to be comfortable with either method!

2 minutes ago, JWD said:

As Rick points out, tails first is useful for gang cutting, so it's always good to be comfortable with either method!

I do this all the time especially when I make boxes. Works well. Very well. All in the journey of joy! Love woodworking!!

No doubt in my mind you'll get this mastered John. As the adage goes "practice makes perfect." The most important take-a-way here is you're getting plenty of shop time in again.

2 minutes ago, Grandpadave52 said:

The most important take-a-way here is you're getting plenty of shop time in again.

Indeed!

I can't believe I am able to get this much shop time in right now, I think I am finally getting used to this retirement thing.🙂