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A list of some of the most frustrating missions from the GTA franchise (Image via Rockstar Games)

7 most difficult missions in the history of the GTA series

The GTA series is infamous for having some of the most difficult missions in video gaming history. Some of them may seem like sudden difficulty spikes, which is especially prominent in the 3D Universe era games like the GTA Trilogy. Even the HD Universe games, which are usually less frustrating in terms of missions, throw in one or two annoying missions that most players get stuck in.

Here's a list of incredibly difficult and frustrating missions from mainstream Grand Theft Auto titles.


Note: This article is subjective and only reflects the writer's opinions.

7 hardest missions in the GTA series that players were stuck on


1) Espresso-2-Go! - GTA 3


Grand Theft Auto 3 was the first 3D game in the series, and the game mechanics aren't as polished compared to later titles. The controls feel janky, the aiming and combat aren't enjoyable, and driving feels quite arcade-like. Modern gamers might find most missions frustrating, but a few take top spots in difficulty.

The hardest one, which almost every player would agree, is Espresso-2-Go! where Claude must race against the clock to destroy nine coffee stalls in eight minutes. The problem is that these are scattered across all three islands, and there's no in-game map; this mission feels much easier in the Definitive Edition remaster, which has one.

2) Demolition Man - GTA Vice City


This mission from GTA Vice City has probably been the cause of nightmares for many. Demolition Man can be too easy or difficult, with most agreeing on the latter.

Here, players must control an RC helicopter to drop off bombs on a construction site. This helicopter is not easy to control, and it will constantly be attacked by the on-site security guards. To top it off, players have less than eight minutes to finish the mission once they pick up a bomb.

The easiest way to beat this mission is to kill the security guards and construction workers with the RC helicopter's rotors before collecting any of the bombs.

3) Wrong Side of the Tracks - GTA San Andreas

Wrong Side of the Tracks is by far the most popular among all the difficult missions throughout the Grand Theft Auto franchise. CJ is tasked to follow a train on a Sanchez while Big Smoke rides on and tries to shoot at the Vamos gang members perched on the train.


However, Smoke is a terrible shot and takes ages to kill them. The moving train doesn't make it easy either, as players must maneuver through and avoid all sorts of obstacles.

Failing this mission results in Smoke's iconic but annoying line, "All we had to do, was follow the damn train, CJ!" The mission's popularity even led to it being included as an Easter egg in Cyberpunk 2077.

4) Learning to Fly - GTA San Andreas

Grand Theft Auto San Andreas was the first game to include flyable aircraft, and Rockstar wanted players to know that very well. Anyone who wants to progress in the main story must pass a series of excruciatingly difficult flying school tests to get their pilot's license.

These tests force players to do some insane stunts, which can take a while to master. They start off with the basics but hit a difficulty spike quite fast. The aircraft controls aren't intuitive, and like most other frustrating missions on this list, every test has a time limit.


5) Free Fall - GTA San Andreas

If Flight School wasn't enough to afflict aerophobia, Free Fall is guaranteed to do that. Players must fly a plane miles into the sea and catch up with another plane to do a mid-air stunt. The thing is, CJ is given a Dodo, one of the slowest aircraft in the game, and the target is a Shamal, one of the fastest.

The target is approaching San Andreas, while CJ has to fly out toward it. One wrong move is all it takes to fail the mission, as catching up is impossible. Completing it needs sheer luck or a trial-and-error approach since players have no idea where the target plane is until it's too late.

6) Paper Trail - GTA 4

In Grand Theft Auto 4, players could only fly helicopters, and they were much harder to maneuver compared to previous titles. In Paper Trail, the clunky controls become incredibly hard to tolerate as one gets to fly a helicopter during this mission.


The helicopter must be aligned for Jacob to launch rockets at another helicopter. However, he frequently misses his target, and players must keep tailing their target and get as close as possible.

7) Derailed - GTA 5

Derailed seems to be a throwback to Wrong Side of the Tracks and proves that Rockstar likes to troll players with frustrating missions. Much like the mission in GTA San Andreas, players ride a Sanchez and must follow a train. However, the difficulty is significantly raised by making landing the dirtbike on top of the train mandatory.

This was possible in Wrong Side of the Tracks as well, but it required immense skill or sheer luck. Making such a stunt necessary only means that many GTA 5 players had to retry this mission several times.

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Edited by
Angad Sharma
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