Fingerboarding looks simple until you actually try to control a tiny skateboard using only two fingers. An ollie can take days or weeks to understand. A clean kickflip may take months. Then, once you start combining flips, spins, stance variations and obstacles, the difficulty level becomes almost ridiculous.

So what are the hardest tricks in fingerboarding?

There is no single answer. Some riders can tre flip all day but cannot land a heelflip. Others can do impossibles but struggle with a basic kickflip. Community discussions repeatedly show that the hardest trick is often highly individual, but a few tricks and combinations appear again and again as serious challenges.

1. The Heelflip

Yes, one of the most frustrating tricks in fingerboarding is also one of the basic flip tricks.

For many riders, the kickflip comes naturally. The finger movement feels intuitive and the board has a predictable flick. The heelflip, however, requires a completely different motion and timing.

The problem is that your front finger can easily interfere with the board. Instead of getting a clean rotation, the board may barely flip, rocket sideways or produce something that looks suspiciously like a kickflip.

Some experienced fingerboarders can perform difficult combinations, impossibles and hardflips while still struggling to make their heelflips consistent.

Difficulty: 7/10
Clean and consistent: 9/10

2. Nollie and Switch Heelflips

Now take an already difficult trick and perform it from the opposite end of the board.

Nollie and switch tricks require your fingers to reverse movements that may have taken years to develop. The muscle memory that makes a regular kickflip automatic suddenly becomes almost useless.

The switch heelflip and nollie heelflip are frequently mentioned as major difficulty barriers because they combine awkward finger positioning, reversed timing and a difficult flick.

Difficulty: 9/10

3. 360 Inward Heelflip

This is where things start getting ridiculous.

A 360 inward heelflip requires the board to perform a full 360-degree shove-it rotation while simultaneously completing a heelflip.

The problem is control. Generating enough rotation is one thing. Keeping the board underneath your fingers, getting the correct flip, catching it and landing bolts is something else entirely.

Experienced riders in fingerboarding discussions have specifically singled out the 360 inward heel, particularly switch versions, as one of the most difficult realistic flatground tricks.

Difficulty: 10/10

4. Lazer Flip Variations

A regular lazer flip is already a serious technical trick: a 360-degree frontside shove-it combined with a heelflip.

On a fingerboard, the extra rotation makes it incredibly easy to lose control. The board can over-rotate, fly away, under-flip or disappear somewhere behind your hand.

Then there are the next-level variations:

• Switch lazer flips

• Nollie lazer flips

• Lazer flips into grinds

• Lazer flip lipslides

• Double or late-flip combinations

Riders often report that lazer flips become easier once the motion finally "clicks," but getting to that point can take a huge amount of trial and error.

Difficulty: 9/10
Switch/nollie versions: 10/10

5. Hardflips and Inward Heelflips

These tricks are confusing because multiple rotations happen at once.

A hardflip combines a kickflip with a frontside shove-it, while an inward heelflip combines a heelflip with a backside shove-it. On a fingerboard, separating the flick and spin enough to make the trick look clean is extremely difficult.

A messy version might technically rotate correctly, but a clean hardflip or inward heel with proper control, height and catch is a completely different achievement.

The inward heelflip, in particular, is frequently described by riders as a personal nightmare.

Difficulty: 9/10

6. Impossible Variations

The impossible is one of those tricks that can either feel surprisingly natural or completely impossible — hence the name.

Instead of simply flipping across the board's width, the deck wraps around the back finger in a vertical rotation. The timing has to be precise enough to allow the board to rotate without your other finger blocking it.

Then things get much harder:

• Front-finger impossible

• Nollie impossible

• Switch impossible

• Double impossible

• Impossible into a grind

• Impossible late flip combinations

Impossible variations require excellent finger control because the board is often rotating in a direction that feels completely unnatural.

Difficulty: 8–10/10 depending on the variation.

7. Late Flips

Late flips are where normal fingerboarding logic starts to break down.

The rider first performs one trick, then adds another flip after the initial rotation is already underway. This means you cannot simply throw everything into one motion.

Examples include:

• Tre flip late kickflip

• Kickflip late impossible

• Double kickflip late impossible

• Hardflip late flip

These tricks require timing, patience and a ridiculous amount of hand-eye coordination.

One fingerboarder described a double kickflip late impossible as possibly the hardest trick they had ever landed — and then attempted to add yet another late kickflip.

Difficulty: 10/10+

8. Double and Triple Flip Tricks

A single kickflip is difficult enough. Now try doing two or three while maintaining enough height to catch the board.

Double kickflips and double heelflips require:

1. A powerful pop.

2. A controlled flick.

3. Enough height.

4. Accurate rotation.

5. A catch before the board hits the ground.

Triple flips take this even further. The difficulty isn't just getting the board to rotate — it's making it look intentional rather than accidentally launching your fingerboard into another dimension.

Difficulty: 9–10/10

9. Switch Tricks Into Grinds

Landing a difficult trick on flat is one thing. Doing it directly into a grind is another level.

Consider:

• Switch kickflip 50-50

• Switch heelflip noseslide

• Nollie inward heel 5-0

• Switch lazer flip lipslide

• Nollie tre flip crooked grind

Now the board must rotate correctly and land at exactly the right angle and position on the obstacle.

Fingerboarders often discover that they can land tricks consistently on flat but completely lose them when attempting to enter a grind.

Difficulty: 10/10

10. Technical Grind and Flip-Out Combinations

Some of the hardest fingerboarding tricks aren't necessarily the biggest spins.

Sometimes the real difficulty comes from combining precise grinds with a technical exit.

Examples include:

• Kickflip back tailslide kickflip out

• Nollie flip crooked grind

• Lazer flip noseslide

• Switch flip 5-0

• Tre flip noseslide nollie flip out

• Inward heel lipslide

The challenge is that every part of the trick has to work perfectly. You need the correct flip, the correct approach angle, a stable grind and enough control remaining to flip out.

One mistake at any stage means the trick is over.

Difficulty: Depends on the combination, but many are solid 10/10 tricks.

So What Is the Hardest Trick in Fingerboarding?

If we are talking about a single trick, switch or nollie 360 inward heelflips have a strong claim to the title.

If we are talking about pure insanity, then late-flip combinations such as a double kickflip late impossible belong in a category of their own.

But perhaps the real answer is simpler:

The hardest trick in fingerboarding is the one you cannot land consistently.

One rider may have switch tre flips on lock but spend years fighting a heelflip. Another might find impossibles easy while being unable to understand nollie flips. That is one of the things that makes fingerboarding so addictive — there is always one trick that seems completely impossible.

Until, eventually, you land it.

And then you immediately start trying it switch.