How to Drill Angled Holes Into Wood

  • 01 of 06


    Drilling into wood at an angle
    Studiobox/Getty Images

    Drilling angled holes—sometimes called pocket holes—is a helpful skill and even is necessary for so many home-related projects.

    One familiar example is when you want to nail a two-by-four at a 90-degree angle into another two-by-four 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 would help immensely by guiding the nail at the correct angle and reducing the amount of hammering needed. 

    But drilling angled holes in wood comes with its unique set of problems. Perhaps the most frustrating problem is when the drill bit begins 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 will greatly improve the possibility of a perfect angled hole.

    Methods for Drilling Angled Holes

    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.

    Manual Method

    The manual method requires no special tools. Along with finesse and patience, you only need a corded drill or a cordless 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.

    Project Limitations

    You will not be able to drill holes at every angle manually. 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 enough of a starter hole to complete the rest of the hole.

    Also, softer woods work better than harder woods. Softwoods, a category which includes pine, hemlock, and the wood found in most two-by-fours, work best for manual angle-drilling. Hardwoods like maple, walnut, and oak are difficult to manually drill at an angle.

    Project Metrics

    • Working Time: 2 minutes
    • Total Time: 5 to 10 minutes
    • Skill Level: Beginner
    • Materials Cost: $0 to $20

    Tools and Supplies You Will Need

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  • 02 of 06

    Start With a Half-Sized Bit

    Choosing a set of drill bits
    Lee Wallender

    Decide on the size of the intended hole, then choose a bit that is about half of that diameter.

    For example, if you want a 1/4-inch diameter hole, choose a starter bit that is around 1/8-inch. Just be cautious of using extremely thin bits, as they may break.

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  • 03 of 06

    Drill a Shallow Pilot Hole at 90 Degrees

    Drilling a pilot hole at 90 degrees
    Lee Wallender

    With that starter bit in your drill, begin to drill a hole in your material at 90 degrees. Do not complete the hole.

    Stop the drill when the bit is about 1/16-inch to 1/8-inch into the material. The aim is to produce a hole that is not so long that it fully establishes the 90-degree angle. If the hole is too deep, you will not be able to perform the next step of changing the angle of the hole.


    Using newer, sharper drill bits helps, since sharp bits grab onto the wood better than dull bits.

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  • 04 of 06

    Shift the Pilot Hole to the Desired Angle

    Shift the pilot hole to the intended
    Lee Wallender

    With that half-size bit still in your drill, remove the bit and the drill from the hole. Move the drill to the desired angle. Place your bit back in 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 into the hole, you will not be able to move your drill at an angle. Now drill the hole, maintaining a slow and steady speed.


    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.

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  • 05 of 06

    Switch to a Larger Bit

    Switching bits while drilling at an angle
    Lee Wallender

    Remove the bit from the drill. Change to the larger bit of the desired diameter.

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  • 06 of 06

    Make a Hole of the Desired Angle and Diameter

    Enlarging a hole while drilling at an angle
    Lee Wallender

    With the correctly sized drill bit, enlarge the angled hole. Go as slow as possible. High speeds may cause the bit to move away, even with that pilot hole you earlier drilled. Also, the heat produced by friction at high speeds may contribute to bit breakage.


    If you need extra room for drilling at low angles, add a drill bit extender. This inexpensive tool chucks into your drill, allowing you extra room for tight side-drilling.