Quick answer

📋 Enable pen pressure in Adobe Illustrator:

Install Wacom driver (required even for non-Wacom tablets)
Install Adobe Illustrator 2020 (request from Adobe Support)
Enable permissions in System Preferences
Change brush setting from "Fixed" to "Pressure"

🖊️ What You Need

In newer versions of Adobe Illustrator on macOS, pen pressure support requires two things:

Install a Wacom driver on your Mac
Install Adobe Illustrator 2020

💡 Tip: You don't need a Wacom tablet to install the driver. This workaround is recommended by Adobe for non-Wacom tablets too.

🔧 How to Set It Up

Step 1: Install Wacom Driver

Download and install the Wacom driver from [Wacom Drivers]

Step 2: Get Illustrator 2020

Illustrator 2020 isn't available directly through Creative Cloud anymore.

⚠️ You'll need to request it from Adobe Support. Make sure you have an active Creative Cloud subscription and let them know you need Illustrator 2020 to enable pressure sensitivity. [Contact Adobe Support]

Step 3: Enable Permissions

Open Illustrator 2020 - you'll see a prompt asking for permission for "TabletDriver." Click OK
Close Illustrator 2020 and open your current version of Illustrator
In Illustrator, go to brush settings and change from "Fixed" to "Pressure"

⚠️ Important: You'll need to keep Illustrator 2020 installed on your Mac - it's required for pressure support to work in newer versions.

🔄 Troubleshooting by macOS Version

🍎 macOS Catalina Issues

If pen pressure is still greyed out on macOS 10.15 after installation:

System Preferences > Security & Privacy > Privacy > Accessibility - make sure com.wacom.IOManager is enabled
Restart your Mac - you should get another "TabletDriver" prompt. Click OK
Check Automation permissions: System Preferences > Security & Privacy > Privacy > Automation - ensure "TabletDriver" is enabled for Illustrator
Open Wacom Desktop Center app from Applications > Wacom Tablet folder. Accept prompts, then quit and reopen Illustrator
Restart Mac again - you should now be able to change brush option from "Fixed" to "Pressure"

🍏 macOS Mojave Setup

If you're using macOS Mojave (10.14):

Install Wacom driver first
Open Illustrator - you should get a permission request
If you clicked "Don't Allow" by accident, enable manually:
- System Preferences > Security & Privacy > Privacy > Automation
- Under Adobe Illustrator, check "WacomTabletDriver" is enabled