Buying an iPad and Apple Pencil used to be simple. You bought the tablet, you bought the white stick, and you started drawing. Done.
Not anymore.
Honestly, the current lineup is a bit of a headache. If you walk into a store today, you’ll find four different Pencils and a dozen different iPads. Some charge magnetically. Some need a cable. Some literally won’t even "talk" to each other despite looking identical.
I’ve seen people drop $1,000 on a shiny new M4 iPad Pro only to realize their perfectly good Apple Pencil 2 is now a high-tech paperweight. Apple moved the internal magnets and charging coils to make room for the landscape camera. That's great for Zoom calls, but it's a disaster for your wallet if you're upgrading from an older setup.
🔗 Read more: iPhone 15 Apple Case: What Most People Get Wrong
Let's cut through the marketing fluff and figure out which pairing actually makes sense for how you work.
The Compatibility Trap: Why Your Old Pencil Might Be Useless
This is where most people get burned. You'd think a "Pro" pencil would work with a "Pro" iPad, right? Kinda.
The Apple Pencil Pro is the new gold standard. It’s got haptic feedback, a squeeze gesture that opens tool palettes, and a "barrel roll" feature that lets you rotate the pen to change the orientation of your brush strokes. It’s incredible. But it only works with the M4 iPad Pro, the M2/M3 iPad Air models, and the newest iPad mini (A17 Pro).
If you have an older iPad Pro—even the beefy M2 version from a couple of years ago—the Apple Pencil Pro won’t even pair.
On the flip side, the Apple Pencil 2 is the one most of us are used to. It sticks to the side and charges wirelessly. It works with the older iPad Air (4th and 5th gen) and the iPad Pro models made between 2018 and 2022. But try to stick it on the side of the newest 2024 or 2025 models? Nothing. It won't charge. It won't connect.
Then there’s the Apple Pencil (USB-C). This one is basically the "budget" option. It’s cheaper, sure, but it lacks pressure sensitivity. If you’re an artist, stay away. If you just want to take notes in a meeting or sign some PDFs, it's actually a solid, reliable choice because it works with almost every iPad that has a USB-C port.
Which iPad and Apple Pencil Combo Should You Actually Buy?
Choosing the right pair depends entirely on whether you're trying to create a masterpiece or just survive a lecture.
The Professional Power Couple
If you're a digital artist or a pro animator, you're looking at the iPad Pro (M5) and the Apple Pencil Pro.
- The Screen: You get that gorgeous Ultra Retina XDR display. It’s OLED, so the blacks are actually black, not just dark gray.
- The Pencil: The squeeze gesture on the Pencil Pro is a game-changer for workflow. You don't have to constantly tap the screen to change colors; you just squeeze the barrel.
- The Reality: It’s expensive. You’re looking at a setup that easily clears $1,000.
The Student's Sweet Spot
For most people, the iPad Air (M2 or M3) paired with the Apple Pencil Pro is the smarter buy. You still get the "Pro" pencil features—the haptics and the squeeze—but you save hundreds by skipping the OLED screen and the M5 chip that you probably don't need for taking notes in Notability or GoodNotes.
The Budget Note-Taker
If you just want a digital notebook, grab the base iPad (11th gen or A16) and the Apple Pencil (USB-C).
- You lose pressure sensitivity.
- You have to plug the pencil in to charge it (kinda annoying).
- You save a ton of money.
What Most People Get Wrong About Pressure Sensitivity
I hear this all the time: "I'm not an artist, so I don't need pressure sensitivity."
That’s a mistake.
Pressure sensitivity isn’t just for painting. It’s what makes digital handwriting feel "real." When you press harder with a real pen, the ink spreads slightly. The Apple Pencil 1, 2, and Pro all mimic this perfectly. The Apple Pencil (USB-C) does not.
Writing with the USB-C model feels a bit more like writing with a fine-liner marker that never changes thickness. It’s functional, but it’s less "organic." If you’re going to be writing for four hours a day in grad school, your hands will notice the difference.
✨ Don't miss: Why April 24 2025 is the Date Everyone in Tech is Watching
The Stealth Choice: iPad mini and the Pencil Pro
Nobody talks about this, but the iPad mini (A17 Pro) is secretly the best digital planner on the market. It’s small enough to hold in one hand like a physical Moleskine notebook, yet it supports the full Apple Pencil Pro feature set.
Most people think the mini is just for reading or gaming. But for architects on a job site or doctors doing rounds, the ability to have a fully-featured Apple Pencil Pro on a device that fits in a lab coat pocket is huge.
Getting the Most Out of Your Setup
Once you’ve actually picked your iPad and Apple Pencil, there are a few things you should do immediately to make it feel less like a tablet and more like a tool.
- Check your nib: They wear down. If the tip of your Pencil feels scratchy or you see the metal core peeking through, replace it immediately. A worn-out tip can actually scratch your iPad's glass.
- Use "Hover": If you have an M2/M3/M4/M5 iPad, your Pencil can "hover" over the screen. It shows you exactly where your mark will land before you touch the glass. It sounds like a gimmick until you use it to preview a brush size in Procreate.
- Customize the Squeeze: If you have the Pencil Pro, go into Settings > Apple Pencil. You can change what happens when you squeeze. I personally set mine to "Show Tool Palette," but you can set it to "Switch between current tool and eraser" if you’re doing heavy-duty sketching.
Final Reality Check
Don't buy more than you need. The M5 iPad Pro is a literal supercomputer, and 90% of people use it to watch Netflix and check email. If you aren't doing 4K video editing or complex 3D rendering in Shapr3D, the iPad Air is more than enough. Just make sure the Pencil you buy actually sticks to the side of the tablet you chose.
Next Steps for Your Setup:
- Verify your model: Open Settings > General > About on your iPad to see exactly which generation you have before buying a Pencil.
- Check the magnets: If you’re buying used, bring your iPad with you to make sure the Pencil pairs and stays attached.
- Update your software: Features like the "Squeeze" gesture require the latest version of iPadOS to function correctly.