How to Drill Angled Holes Into Wood

drilling a hole at an angle

The Spruce / Margot Cavin

  • Working Time: 10 mins
  • Total Time: 2 mins
  • Skill Level: Beginner
  • Estimated Cost: $0 to $20

Drilling angled holes is a helpful skill that comes in handy for many home-related projects. One familiar example is when you want to nail a 2x4 at a 90-degree angle into another 2x4 to create the framework for a wall, yet you don't have a lot of room to swing the hammer. Toenailing is the answer for tight areas like this. If you have a hard time getting the nail started, a short angled pilot hole helps immensely by guiding the nail at the correct angle and reducing the amount of hammering needed. 

Another example, common in woodworking projects, is drilling pocket holes when two pieces of wood need to be joined at an angle, and where you want the screw heads to be recessed below the surface of the workpiece.

But drilling angled holes in wood comes with its unique set of problems. Perhaps the most frustrating problem is when the drill bit begin to bore correctly, then quickly skitters across the wood and out of position. This is why you need to take special measures—either by purchasing a tool that will do the job for you or by adopting a technique with your drill that improves the likelihood of a perfect angled hole.


Click Play to Learn How to Drill Angled Holes

Three Methods for Drilling Angled Holes

There are three common methods for drilling angled holes, but two of them are more appropriate for experienced woodworkers who can afford the tools.

Drill press: drill press is the best way to drill a hole at an angle. However, a drill press is an expensive, bulky, standalone tool that only lets you work on small pieces of material. Drill presses are poorly suited for so many home improvement projects because they cannot be moved from the shop.

Pocket hole jig: A good alternative to a drill press is a pocket hole jig. Pocket hole jigs, such as the Kreg R3 Jr., are cheap, simple devices that guide your drill bit into the material at an angle. If you need to drill more than a few holes, it may be worth purchasing a jig like this. Pocket hole jigs are not foolproof, though. They still require some practice time before moving onto the actual work material. And a good pocket hole jig is a fairly expensive accessory, especially if you won't use it regularly.

Manual method: The manual method requires no special tools. Along with finesse and patience, you only need a drill and a set of good drill bits. One bit will be the size of the intended hole and the other bit will be around half the size of the intended hole. This method has some limitations, though:

  • You will not be able to drill holes at every angle with the manual method. Up to 45 degrees, you can easily drill an angled hole. Between 45 degrees and 15 degrees, the process becomes more difficult but not impossible. Lower than 15 degrees, the drill will move around too much. When the starter bit dances too much, you cannot establish a well-defined starter hole to complete the rest of the hole.
  • Softer woods work better than harder woods. Softwoods, a category which includes pine, hemlock, and the wood found in most framing lumber, work best for manual angle-drilling. Hardwoods such as maple, walnut, and oak are difficult to manually drill at an angle.

What You'll Need

Equipment / Tools

  • Drill
  • Drill bit set
  • Speed Square
  • Pencil


materials for drilling holes at an angle
The Spruce / Margot Cavin  
  1. Choose Drill Bits

    Choose a bit with a diameter that matches the final hole size you plan to drill, then choose a starter bit with a diameter about half that size. For example, if you want a 1/4-inch diameter hole, choose a 1/8-inch starter bit. Just be cautious of using extremely thin bits, as they may break.

    choosing the drill bits
    The Spruce / Margot Cavin 
  2. Drill a Shallow Pilot Hole at 90 Degrees

    With the starter begin to drill a hole in your material at 90 degrees to the face of the workpiece. Do not complete the hole. Stop the drill when the bit is about 1/16-inch to 1/8-inch into the material. The goal is to drill hole just deep enough to hold the tip of the bit for the next step, in which you will change the angle of the hole.

    • Tip: Using newer, sharper drill bits helps, since sharp bits grab onto the wood better than dull bits.
    drilling a pilot hole
    The Spruce / Margot Cavin  
  3. Shift the Pilot Hole to the Desired Angle

    Pull the starter bit back from the horizontal hole, and move the drill to the desired angle and insert the bit back into the hole. Make sure that the bit is firmly seated in the hole—if it is too close to the edge, it will lose grip and dance away; if it is too deep , you will not be able angle the drill. Now drill the hole to its full depth, maintaining a slow and steady speed.

    • Tip: Rather than guessing at the angles, using a Speed Square helps you strike a perfect angle. Just lay the square against the side of the board, tilt it to the intended angle, then draw a line on the side of the board.
    drilling at an angle
    The Spruce / Margot Cavin 
  4. Switch to a Larger Bit

    Remove the starter bit from the drill. Now, insert the larger bit into the drill.

    changing out bits
    The Spruce / Margot Cavin 
  5. Drill the Final Hole

    With the correctly sized drill bit, enlarge the angled hole to its final size. Go as slow as possible, since high speeds may cause the bit to move away from the pilot hole.

    • Tip: If you need extra room for drilling at low angles, add a drill bit extender. This inexpensive tool secures into the drill chuck, allowing you extra room for tight side-drilling.
    drilling the final hole
    The Spruce / Margot Cavin