Hand Lettering on the Surface Pro

Brush Lettering on the Microsoft Surface Pro

As hand lettering has increased in popularity, one of the challenges we face as artists is trying to figure out how to balance this hand-drawn art with modern technology. There are several ways to get your lettering from the page onto the computer screen to be used as digital images and overlays {see this photo tutorial for more on that}. But what about creating your art both digitally and by hand at the same time?

Recently, my lettering mentor Dawn Nicole shared a video tutorial on Facebook for how to do brush style lettering directly on the iPad Pro with the help of an Apple Pencil. It was amazing. It was inspiring. And it was useless to me because I don’t have an iPad. Just a few months ago, I invested in a Microsoft Surface Pro 4 instead, and I was determined to figure out how to do the same thing on that instead! Here’s what I came up with and how you can create hand lettered art on the Surface Pro.

Tools you’ll need

Microsoft Surface Pro Tablet
Microsoft Surface Pen
Adobe Illustrator

I downloaded a free trial version of Adobe Illustrator to see what the capabilities were before I purchased it. You can find it on Amazon for $19.99/mo, as well as the free 30-day trial if you want to test it out first {affiliate link}. I wish it were less expensive, but I figure it’s cheaper than purchasing another tablet!


This is what you’ll see when you open Adobe Illustrator. If not, click on the drop down menu at the top next to the search bar and make sure it’s set to “painting.”


In the bottom right corner, you’ll see a Brushes menu. Select the little icon that looks like a page with the corner turned up all the way at the bottom of your screen. This will allow you to create a new brush. The following menu will pop up in the center of your screen and ask what type of brush you want to make. Select Calligraphic Brush {if it’s not chosen already} and click OK.


Next, adjust your brush settings. Set the angle to anything you like between 30-60 degrees. I leave my roundness at 100. You can adjust the size to whatever you like, but I find that something in the 7-9 pt range is my preference. The next part is the key to making this work; click the dropdown menu and change it from “fixed” to “pressure.” This is what will allow the program to respond to the amount of pressure you apply to the pen/stylus like a brush pen would. Finally, click the Variation menu and set it to one numeral below whatever your size is. You’ll see three dots displayed in the white box, showing you the thickness of your lines with light, medium, and hard pressure. Name your brush whatever you like, then click OK.


There’s one more setting we need to put in place. Click the paintbrush icon on the left of your screen. Adjust the fidelity setting so that it’s closer to Accurate than Smooth.


Now you’re ready to give it a try!

Lettering on the Surface Pro

To start, I practiced just like I did when I was first learning brush calligraphy with a pen and paper. Make a series of thin upstrokes by using very light pressure, then a series of thicker downstrokes with more pressure. Try alternating them to get a feel for switching back and forth.


There is most definitely a learning curve! Even if you are a master of brush calligraphy, your first few {or fifty} designs aren’t going to look the way you expect. Just as it takes time, repetition, and muscle memory to learn the technique the first time around, the same is true when you switch to this digital method. The Surface Pen and the sensors react differently to pressure than your pen, and there’s a little bit of a delay you won’t be used to at first. Fortunately, it’s very easy to erase your mistakes! Just be patient and keep on practicing.

Once you get the feel for it, you can play around with your brush settings, the view, and other settings in Illustrator and see what you like best.


When you save your art, it will save as a .ai file, so if you want it in a different format, choose Select All, then Export. This will give you the option to save as a .jpeg which you can use and share easily. What do you think, fellow non iPad owners? Is this something you’d like to try?


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  1. Hi, this tutorial is tab and I have followed all the advised steps and I can use it to create lovely lettering however the pressure doesn’t seem to be working? For example, there is no difference in line thickness regardless of the pressure I am applying. Do you have any other tips to resolve this? What is your pen pressure for the surface set at? Thank you 🙂

    1. Ultimately, I found that the Surface just wasn’t as responsive to pressure as I hoped it would be. I ended up investing in an iPad Pro just last week…it makes a HUGE difference. The Apple Pencil and the Procreate app are magical.

  2. Amy!!
    I’m so glad to see you have the Surface Pro! I have it on my wish list. I have the Cintiq but, I need something portable, that can handle the apps I’m already using! And.. well.. I’m a PC kind of girl. 😉
    Keep up the awesomesauce!!
    Kristin (KHolt)

    1. Kristin, I have to tell you that since I wrote this post, I bought an iPad Pro…the difference for lettering is night and day. I use the Surface as my laptop {I’m a PC gal too} but I use the iPad for all my lettering and design. There’s just no comparison.

  3. THANK YOU!! I have been trying to do lettering with illustrator but couldn’t quite get it to cooperate. You gave me just the tips I needed to get it to work! {{BIG HUGS}}

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