I don't have a drill press, so when drilling a long hole, I'll typically drill from both sides, as close as I can eyeball being orthogonal to the surface, and meet in the middle. This way, the series of aligned holes on the front are also aligned on the back side.

Now I'm making drawbores with multiple pegs per tenon, and wondering if it's a bad idea to do the same thing.

If there's plenty of stock to drill through and support the peg, would it be okay to drill, say, 3/4 of the way on one side, and try to meet from the other side?

frontback each leg (4x6) has 4 drawbored pegs. 2 pegs per mortise. after seeing how terrible my drilling was, i decided to make the long edge peg not stick through — they would have intersected paths anyway. luckily it’s called the back side because it’s at the back


Maybe I'm obsessing over details, but that part always seems to be omitted from instructions (maybe for a good reason, I don't know). Most videos I've watched on the topic, they drill only from one side until the snail/brad point starts poking out, and then pop a clean rim for the remaining 1/16" from the back side. This is the sensible approach, of course, because it makes a straight path for the peg, and a clean exit hole but it does tend to create ugly alignments on the backside (in my experience).

  • 2
    You can always get a long bit with a 1/8" diameter to drill all the way through and then use that hole as a pilot for the full size bit.
    – Ashlar
    Jan 12, 2022 at 23:52
  • @Ashlar, yes but what if that 1/8" hole is drilled skew? Once you have a pilot hole it's nearly impossible to steer a bit so it doesn't follow it, so the initial problem of drilling square to the surface remains. (Plus if the OP wants to use an auger it's important not to have a pilot hole.)
    – Graphus
    Jan 13, 2022 at 22:20
  • 1
    One way to avoid most of the tear out on the backside is to (firmly!) clamp a sacrificial piece to it. And just to ramble on a little… a long 1/8” drill bit isn’t very rigid and can wander off straight in a long hole. Jan 14, 2022 at 12:46
  • Thanks for adding the photos. Rest assured, these kinds of results are not unusually bad by any means! I've done worse myself LOL But more than that, I've drilled holes that drifted off the line about this much or even a little more when doing my very bestest to be careful, e.g. by using the ring trick when boring with braces and eggbeaters. That trick is not at all as reliable as its reputation suggests..... as you can also see numerous times when James Wright of Wood by Wright uses it!
    – Graphus
    Jan 15, 2022 at 19:03
  • 1
    Also, bear in mind that so long as the holes in the tenons line up with the angle of the holes you drilled, the pegs will still do their job. Insert the tenon, set your brad-point bit in the hole and give it a tap to mark the center point on the tenon, then use your sliding T-bevel to mark the angle. Drill your holes in the tenon at the same angle as the holes through the mortise and all is well. Of course, it is easier if everything is 90°... :)
    – FreeMan
    Jan 17, 2022 at 19:32

2 Answers 2


If you're having trouble eyeballing square or plumb as you drill when working solo (so you can't take advantage of a second pair of eyes), which is something I'm convinced most people have trouble with, then simply jig it — make a drilling guide.

That way no matter whether you drill half the thickness each way, 3/4 one way and the rest the opposite way, or almost fully through and then complete that last little bit from the other side, you can be assured you're drilling square to the surface (although in that last case it shouldn't be required to use the jig to complete the hole).

Now some very good drilling guides are made, but it's really easy to make a versatile and reliable perpendicular drilling guide in just a couple of minutes:

enter image description here

Regardless of the jig you buy or make, with many bits being relatively short once fully seated in a chuck you'll run into the problem that the jig itself limits how deeply you can drill. So often you'll have to start the hole jigged and then remove it to complete the drilling, trusting to the start of the hole to guide the drilling the rest of the way.

  • 3
    I love the LEGO drill guide. Brilliant!!
    – FreeMan
    Jan 13, 2022 at 13:21
  • 2
    @FreeMan They're useful for so much more than just stepping on in the dark.
    – gnicko
    Jan 13, 2022 at 14:20
  • Thank you! I think this is saying: "it's a bad idea to drill from both sides because the path of the peg (minus tenon) won't be a straight line and your peg will have to snake around a lot. Instead, assist your drilling to steady your angle and it won't matter". Putting this to the calculator, a 1.0 degree deviation through my 4" thick stock should put me 1/16" off my target on the other side. With 5.0 degrees, it's more than 5/16". Judging on how far off my test holes are when eyeballing, I should go see an optometrist.
    – ww_init_js
    Jan 15, 2022 at 0:19
  • 1
    I wouldn't say it's a bad idea at all, I've done it (and recently!) to help reduce drift errors. But I have done it and had it turn out less well than I'd have hoped when drilling freehand (deliberately, to try to train myself to drill straighter). Anyway, regardless of the approach you adopt a drilling guide is certainly going to help achieve squarer results and there's no shame in using them (same as with a sawing guide) given both were used by pros back in the days of supposedly higher levels of hand-tool proficiency to help ensure consistent results, including e.g. by Shaker craftsmen.
    – Graphus
    Jan 15, 2022 at 18:53
  • 1
    @FreeMan, well regardless of the quality of Shaker furniture jigs still shouldn't be regarded as a crutch for the weak :-) Unlike a lot of freehand sharpeners who seem to be on a permanent crusade to rid the world of honing aids I not only don't mind others using them, I actively encourage newbies and learners to use one (although not to spend a lot of money on one haha). And let's be real here, if we take the anti-jig thing to extremes everyone should be doing pocket screws the same way they did in Ye Olde Days — with a gouge & brace. And if you've never seen the results, they ain't pretty!
    – Graphus
    Jan 17, 2022 at 17:03

Couple of Ideas

  1. there are handy 'drill presses' that can take a regular drill to give you a similar performance to a 'real' drill press. I just bought my sister one for Christmas. Most are between $25-$45. They aren't heavy duty, but to drill straight smallish diameter holes, they are more than sufficient.

  2. Getting 'long' bits. I have a 1/4" bit that is 18" long it cost less than $10, so you should be able to get a 'special' bit for your project.

  3. you seem to have a couple boards that you need to have lined up, Line them up, drill your holes through the first one and a little way into the next, take the first one off the top, then drill most of the way through the bottom board, and when the braid comes through flip it for clean hole. Having a board on the back side when you drill through a board helps keep it clean too.

  • Long, skinny twist bits can be subject to major wandering issues in wood. You can get deflection of more than the diameter without any difficulty if the grain is uncooperative.
    – Graphus
    Jan 17, 2022 at 17:13
  • 1
    I'd never paid much attention to this before, but "jobber-length" term refers to a more or less standard ratio of drill bit diameter to flute length of 1:9 to 1:14.
    – ww_init_js
    Jan 17, 2022 at 18:19
  • @Graphus true, but it's still a 'cheap' way to make long holes.
    – bowlturner
    Jan 17, 2022 at 18:55

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