How To Drill Holes At An Angle In Wood

When I started woodworking some year ago and wanted to screw two pieces of wood together, I had a very specific method. I would hold the wood together bracing it with my knee, angle the screw at what angle I thought it should go in at and pray. Most of time it ended up being a mess and looking pretty miserable. Then I found out about some tools that are designed to make this easy and basically brainless. Here are much better options than what I used on how to drill holes at an angle in wood.


I will be sharing two methods of drilling holes at an angle in wood – the primary method (using a Kreg Pocket Hold Jig) and an alternative method (using a Portable drill guide jig). Both methods are acceptable and get the job done with precision and accuracy.

Kreg Pocket Hold Jig

The Kreg Pocket Hold Jig is a tool that comes handy for DIY enthusiasts like me and those who are new to woodworking. Whether you plan to make simple repairs within your house or you plan to build garage storage shelves, this tool will help you finish the project effortlessly and in less time. 

The Kreg Pocket Hold Jig has a rugged rear-mounted clamp that will hold your wood in position while you apply pressure to the handle.  


  • This tool is perfect for drilling pocket holes on material from ½” to 1 ½ thickness
  • It is easy to set up
  • It is very easy to handle
  • It features a drill guide which is great for home repairs
  • It doesn’t require glue or complicated mathematics
  • The clamping method is great


  • This tool doesn’t support woods vertically
  • Not suitable for small pieces

You will find the following items when you pop the box open:

  • Drill and drive bits
  • Screws in various sizes
  • Depth collar with a hex key
  • Case
  • Clamp pad adapter

How To Use a Kreg Pocket Hold Jig

Step 1: Measure the thickness of the wood you want to drill

This is the first step in your quest to drill pocket holes in wood. Always remember that the strength of the angled holes depends on the wood’s thickness. So bring out your tape and measure the thickness of the wood.

Step 2: Set The Jig Height

Generally, the jig’s height is usually based on the thickness of the wood. Therefore, ensure you raise or reduce the height to match the wood’s thickness. However, if you plan to join woods of different thickness, set the jig’s height to match the smallest thickness. 

Step 3: Set the drill bit’s depth collar

The Kreg Pocket Hold Jig features a collar and a stepped drill bit. Just by adjusting and tightening the collar, you can set the drill bit to your desired depth. Line up the edge of the drill bit to align with the Jig’s marking, and adjust the collar as high as possible before tightening. 

Step 4: Position Wood And Clamp

Position the wood you want to drill on the jig and then clamp the wood so that it won’t slip while you are drilling. The guide marks on the jig are meant to tell you the exact location to drill the angled holes.

At this point, let me share the basic rules I normally use to drill angled holes in wood:

Width of woodAngled hole placement
1” to 2”B and C
2” to 3”A and B
3” to 4”A and C

Step 5: Drill Angled Holes in Wood

Now, push down the drill using the guide holes on the Kreg Pocket Hold Jig. Once the drill gets to the correct height, the collar will automatically stop the tool from further drilling. Ensure you tighten the depth collar very well; otherwise, you won’t get the angled holes you desire to make a strong joint.

There you have your angled holes!

Using Portable Drill Guide Jig

Using a portal drill guide jig is a great alternative to the use of Kreg Pocket Hold Jig. This tool is set up out of the box. I was able to set up my own in about 10 minutes. It is indexed at 0, 15, 30, 45 degrees.


  • It has a built-in protractor scale for drilling accuracy
  • Doesn’t require much assembly
  • It can be adjusted to your desired angle
  • It has a built-in depth stop to guarantee accurate drill depth
  • It features anchoring pins to firm hold woods in position without slipping


  • It may not give you the best precision compared to Kreg Pocket Hold Jig.

How To Use a Portable Drill Guide Jig

  • Use a square or angle guide to measure the angle you want to drill to ensure drilling accuracy
  • Set the portable drill guide jig on the wood while maintaining the correct angle
  • Use a clipper on the base to secure the wood to prevent slip, especially when drilling large diameter holes
  • Punch down the drill guide jig on the wood but avoid using excessive pressure on the handle of the tool
  • Ensure the holes are wide enough for your woodwork projects.
  • Remove the clipper from the base  

If you are a passionate woodworker or DIYer, the Kreg Pocket Hold Jig and Portable Drill Guide Jig are useful to get your project done with less stress. These tools will help to ensure you joinery of wood pieces is precise, rigid, and strong.

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