How to Drill Angled Holes

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Sometimes certain projects will require that you do not drill straight into a piece of wood. You may need to create angled holes from time to time, but this does not have to be a scary, or difficult thing for your to do. There are some necessary tips and tricks that you can follow that will make this process much easier.

Tools Needed For Drilling Angled Holes

The best tool for drilling angled holes is a drill press. This will allow you to get clean, repeatable holes in your material. You can make the same drill over and over again with repetition.

If you don’t have a drill press, or only need to make a quick angled hole, you can use a drill. Plan to have the right drill bits on hand, as this will be really important. A hand drill will take care of your needs in most cases.

Hand holding drill bits

The best drill bit for this kind of job are brad point drill bits. This bit will keep the bit engaged when you stop drilling, making it easier to keep the drill bit on track as you work. These are a simple and common drill bit that you’ll be able to find easily.

If you do not have a brad point bit to hand, you can drill with a regular drill bit, but you should drill a small pilot hole first to make sure that your angle is correct throughout the drilled hole. This will also offer a guide to the drill bit when you drill the larger hole.

How to Drill Angled Holes

Now that you have prepared and have collected your tools and made your plan, you will be ready to start the actual drilling process. Take a look at the item that you are using for a fastener, and make sure that the drill bit that you have selected is the right size for the fastener.

This is a common place that mistakes are made, the worst of which being that the hole that was drilled is too large for the fastener.

If you want to check the angle that you are going to be drilling into the wood one more time, go ahead and measure out all of the measurements again, just as a last check. Your can use a square gauge to check your work if you want additional confirmation.

1. Prepare to Drill

This is perhaps the most important part of the process. You will need to make sure that you have measured correctly and then you will need to use your jig to secure the piece that you are going to be drilling into. The clamping surface of the job is made for this type of work and will help you to hold everything steady as you drill.

Having the wood clamped in some way is always a big plus if you want to make sure that the drill bit does not wander while you are working. You can make your own jig if you need to do so by using some scrap wood.

  • To do this, you will cut the block off at a 15-degree angle, or match the angle of the hole that needs to be drilled.
  • Attach small blocks to it to secure it for clamping and then use it for your clamping surface to stabilize your project as you drill.

Being able to stabilize the surface you are drilling into is essential for a good result at the end of the drilling process. You can probably see by now how hard it would be to eyeball this drilling process!

Planning out the project before you drill is the only way to make sure that your angle hole is at the right angle and is straight.

2. Pick the Right Bit for the Material

While the process will be the same, the type of drill bit you select is vital, and should depend on the specific material you’re drilling into.

Here is a guide on how to drill into a variety of materials:

Each material has different components, such as how hard or soft it is, and how dense the material is.

3. Drill a Pilot Hole

Start out with your pilot hole. Drill at the angle that you have marked out slowly and carefully, pulling the drill in and out of the hole to debur as you go. Do not complete the hole.

This is just the guide hole that you are drilling. Stop when you are about 1/16 inch into the material.

A new, very sharp drill bit is the right choice for this step as it will create a clean hole that will not affect the other, larger bit’s ability to go through the wood or other material at the correct angle. If you need to work with older bits, make sure to sharpen them ahead of time.

4. Redirect the Pilot Hole to Follow the Angle

Now that you have the first part of the pilot hole made, redirect the bit to drill along the angle you have marked out. Hold the drill firmly and work slowly through the thickness of the wood. Make sure to check as you are drilling that you are still working at the correct angle.

This pilot hole will guide the larger drill bit as you make the actual hole for the fastener to seat into. Make sure that you have drilled all the way through the wood before you change to your larger drill bit.

Make sure you’re using a powerful drill. Most likely a good corded drill is best for the job, as they have more power than their cordless counterparts.

Person drilling angled holes in a piece of wood

5. Switch to the Larger Bit

Switch your drill bit to the correct sized bit for your fastener. You will not enlarge the angled pilot hole that you drilled before. You will want to go as slowly as possible as you do this so that you do not slip and make the hole crooked.

The same drilling style is useful here. Make sure that you move slowly and with even pressure. Back the drill out of the hole a few times to deburr the hole and remove any debris.

If you are running into issues getting the drill bit all the way to the bottom of the pilot hole, you can use a step drill bit or a drill bit extender to make this possible.

6. Check that the Fastener Fits

While you should have done this already before you started drilling, you will want to doublecheck that the size of the hole is going to work with the fastener you are using before you try to assemble the pieces that need to be connected.

If the hole is not big enough or is not at the right angle, you could split the wood when you try to insert the fastener.

If the hole looks like it is correct and you have checked the angle one last time, you can attach the two pieces of your project. If the hole has been drilled correctly, the fastener should sink in easily and the two pieces should go together without any struggle.

Why Would you Need to Drill Angled Holes?

Learning how to drill angled holes is essential for a variety of projects, ranging from making furniture to home improvement tasks.

You’ll also need the skill when working in angled spaces where you cannot drive a nail or screw straight into the surface directly. These kinds of holes are often used to toe nail boards together at corners. This is the most familiar need for toe nailing.

You can also toe screw, but this is less common. This is one of the best ways to create tidy corners and to help put together furniture items. If you like to fix things at home, or you are considering doing a home improvement project of some sort, you will probably need to use this skill at some point during the process.

Angled holes are more common than you think and are present in many furniture and other assembled items that you can buy from stores. You probably do not realize how common they are because a lot of home projects do not necessitate this skill set in any way.

However, if you are going to be tackling a home improvement project, or you want to start repairing your own broken furniture, you will need to learn this skill. You will use it on everything from floor installation projects, to furniture refurbishments, or deck building.

Being able to reliably drill an angled hole is a great skill to have in your back pocket for a whole variety of reasons and projects.

Why is This Difficult?

Angled holes can be tough to drill because of a lack of guides for the drilling process. In many ways, you have to develop a freehand method of drilling.

In addition, maintaining the correct angle can be tough when you are working in locations that you cannot see well. This is the reason that tips and tricks for this process can make it much easier.

The best rule of thumb when drilling angled holes is to prepare and measure carefully.

There are some tools, like a drill press, that can make this much easier. but that is not always realistic based on the piece of wood that you are drilling into. It can be tempting to freehand this process but you should avoid this to make sure that you do not waste supplies by drilling incorrect angled holes into surfaces freehand.


Drilling angled holes takes some skill and practice, but careful planning when measuring can mean the difference between a correctly-drilled hole and one that wanders off course as you work. Taking the time to make sure that you have measured correctly and that being mindful of stabilizing the drilling surface can mean the difference between a correctly drilled hole and a ruined piece of wood that cannot be used for your project.

Angled hole drilling is not as hard as it seems with some attention to detail and some preparation before drilling.

An expert at home repair, remodel, and DIY projects for nearly 40 years. His first experience came in completely restoring an antique home. Completely redone from the inside out, and restored to its original form, the home is a featured design by renowned Southern California Architect Cliff May, considered to be the father of the California Ranch Home. Now Dennis spends his time on fine woodworking projects and tool comparisons.