NOTE: Do NOT add missions from Grand Theft Auto V here, this is restricted to the missions featured in Grand Theft Auto Online only! The single-player missions have their own page here.
Some of Lamar's missions in Online require you to (optionally) join someone else and steal a tanker of fuel while evading the cops. Sounds simple, right? Well, the tanker goes about 30 miles per hour at best, is prone to detaching, and you have helicopters after you. And that's not going into the tanker's properties, and the fact that the police have a tendency of shooting and ramming into it.
Another of Lamar's Online missions tasks you with sneaking some lowriders past the cops to be fenced. If either you or your one teammate get spotted, you have to start all over. Then, once you finally do make it to your destination, you get to enjoy a shootout wherein you're beset on all sides by gangbangers.
Right after this mission is "It's a G Thing", which tasks you with rescuing Gerald from police custody. To do this, you just have to blow open the doors of the police wagon he's in and pick him up. Simple, right? Unfortunately, the wagon stops in the middle of the airport tarmac, with no cover to speak of, and about half a dozen cops who will instantly aerate you if you so much as walk near the wagon. Decide to try and whittle down the cops numbers before going in to plant the sticky bomb on the wagon? Too bad, you get a 3 star wanted level once the cops get alerted to your presence, and they start bringing in helicopters and spawning infinitely.
Stocks and Scares, a Lester mission in Online, can be this, as it's one of two missions (the other being Dry Docking) that require opening a safe. Unlike hacking terminals, the safe uses a rather complex unlocking system, where if you turn the wrong way, the lock resets. Add in infinitely spawning enemies and you have a mission that gives all but the most well organized teams frustration. However, it is one of the highest paying missions in Online after the rebalance, so it is worth it.
The Humane Labs Online heist. That One Sidequest mentions two of the setups, and the final mission is just as annoying. There are two teams that each have reasonably difficult tasks, but the worst part is that both groups are separated from each other and can't help the other out. In addition to that, each team has a fairly decent challenge on their hands. All of that makes it the least popular heist. At least you get a massive discount for the Insurgent.
The air team has to deal with trucks and enemy helicopters outside. The helicopters aren't too bad but with only one gunner it can be difficult to avoid taking a missile to the face due to how long it can take for the pilot and gunner to coordinate the assault on the enemy helicopters. Complicating things is the fact that the air team has to focus on both enemy attack helicopters and try to attack enemies on the ground before they get to the labs, as they will approach the ground team from behind, becoming another factor to hurry the ground team. Finally, you need to hope you have the right players on your heist, because helicopter flying and gunning are both skills a player might not have gotten, while fighting on the ground is mandatory to learn for any player. Finally the game doesn't make it clear the gunner can take the chain gunner's seat, rather than the front mounted explosive round cannon, and that it would allow them to switch what side they're positioned on, making coordination much easier, but also subjecting you the A.I.'s pinpoint aim, making the chain-gunner position a liability.
After the ground and air teams finish their initial tasks, the air team is supposed to pick up the ground team. This is arguably the worst part for the pilot (hell, many players say it's the worst part of the heist in general). The pickup point is a beach just big enough for the helicopter to land on, with a small margin for error. Not only that, but it has an upward slope, making the landing even trickier. It is very easy to land in the water, slice up a teammate with your rotors, or smash the rotors against the cliffs, all of which result in heist failure.
The "Prison Break" heist can be a real pain in the ass, even if you manage to assemble a team of trusted players with mics. Two players enter the prison as a guard and prisoner in order to find Rashkovsky and escort them to the airfield, but before that, they have to fight their way past large groups of NOOSE officers. Thankfully, Rashkovsky is very cautious and not likely to die, but if anyone fails the Heist, you'll have to start over practically from the beginning (with the "prisoner" and "guard" entering the prison again). The pilot of the getaway plane doesn't have it much better: they are on a timer to get to the airfield where they will pick up Rashkovsky which stops once they enter Blaine County, at which point they will be beset upon by fighter jets while riding a plane that comparatively lacks maneuverability and no weapons, meaning that unless the pilot is really good (or can slip behind the jet, since they come one at a time), they will be shot down. The demolitions expert is tasked with protecting them with an attack chopper after hijacking a prison bus and torching it, but helicopters in this game are very difficult to control. Finally, if everything goes well, the "prisoner" and "guard" must bring Rashkovsky to the airfield, with the pilot coordinating their landing so they can pick up Rashkovsky and his escort while being pursued by the police with a five-star wanted level, which means that the airfield will quickly get clogged with police vehicles (potentially including the runway). And that's not counting if your luck is really crappy and a helicopter is shot down and crashes into the plane, which sends you right back to the "guard" and "prisoner" entering the prison, demolitions hijacking the prison bus, and the pilot flying to the airfield. Typically, at this point, someone will quit. Finally, if you do manage to take off unscathed, the game may throw you a bug where you can't lose the 5-star wanted level, regardless of how far away the cops are from you, rendering the whole heist unwinnable.
The "Pacific Standard" heist is almost on the same level as "Prison Break". The first third of the heist is simple enough: go into the bank, get to the vault, get the money, and get out. So long as the Crowd Control heist members keep the alarm from going off, the rest of the heist should remain manageable (if still very difficult). Next comes the mad dash to the getaway bikes, having to fight your way through waves of cops; followed by the final getaway, where you and your team make your escape. The journey from the bikes to the escape point is very long and fraught with both rough terrain near the end and bloodthirsty cops throughout (and should the alarm go off during the first third, NOOSE!). Checkpoint Starvation isn't as much of an issue here as in "Prison Break", but there's also the fact that if the heist members carrying the money get shot, they start dropping the money and can't recover it, resulting in a smaller reward. As such, many players had taken to using a Good Bad Bug that let them take another vehicle (most often, an armored Kuruma car) instead of using the bikes, and why the removal of this exploitpissed a lot of players off. Thankfully, there is another bug that lets players escape by stolen helicopter, and clever players can take an armored truck (which can spawn by letting the alarm go off at the bank) down an alternate route to reach the getaway point safely (if more slowly).
The "Silent & Sneaky" approach to the Diamond Casino Heist is the more challenging of the three approaches. Unlike "The Big Con", you're expected to go completely unnoticed by security cameras and guards, lest you have a swarm of enemies come down on you. The good news is that breaking stealth does not fail the heist, but the bad news is that you won't have as much in the war of weapons as if you took the "Aggressive" approach, nor will you have thermal charges for breaking into other parts of the vault, requiring you to hack into keypads, which takes time — time you may not have if the alarm is raised before reaching the vault. If, goodness forbid, the Heist leader didn't take the time to disrupt the Duggan Security shipments, you'll be dealing with heavily armed, heavily armored mooks that will make your life a living hell. Similarly, unlike the Aggressive route’s tunnel and The Big Con route’s Gruppe Sechs uniform, there’s no way to enter the casino close to the vault, forcing you to sneak your way through the whole casino.
With the right tools though it is possible to make the Silent and Sneaky easy:
1: The Stun gun can disable cameras temporarily, allowing you to bypass tight spots.
2: Weapons have suppressors which allows you to shoot guns without alerting the guards unlike the Big Con.
3: You can shoot down one camera in case either you shoot a guard near a swiveling camera which would alert the guards if it sees a dead body, or if there's an enemy that stays in one place near the camera.
4: The Duggan shipments would allow you to shoot all enemies down, as they won't have the helmets when you take down at least three shipments.
5: You can use an EMP to take out the power for a couple minutes, along with the infiltration gear with night goggles which allow you to have better sight during the dark than the guards.
6: You can also use nano drones to take out any guards that would be hard to get to.
The online mission for the biker club where you have to deliver product in mail vans is considered to be the worst mission for drug running. Not only do the vans go incredibly slow, but your destinations are always miles apart from each other and you will eventually have to take a road that goes uphill, which the van can barely handle. If you want to make more money, you have to drive multiple vans, which can still take a long time even with a proper crew. Unless you are playing with friends only, expect to be easily picked off by other players hunting you down in your slow ass van.
Most of the Gunrunning delivery missions are disliked due to being a combination of gimmicky and difficult with several being impossible to do alone if you're moving enough product, forcing a seller to trust in the competence of their assistants. Special hatred is reserved for the Dune FAV one, however, which requires the players to drive up to 4 Dune FAVs to a series of delivery spots to make drops. Each Dune FAV must make all five drops, for a total of 20 if you have four vehicles, and you get attacked by waves of NPCs each time a drop is made. The Dune FAVs you're given are hard to control and can be destroyed in a few inches of water, the locations can be very far apart, and the whole mission is timed giving only 15 minutes for all drops to be made. It's generally considered even worse than the infamous mail-van delivery mission listed above, even if no other players decide to come after you.
After Hours adds Business Battle missions, which happen every 15 minutes automatically* as long as there are no other freemode events going on and at least 3 players are not in a mission already, yield a consistent 2 cargo worth base $9,000 each (the sale price, minus Tony's cut), so they end up being not bad, yet not good in terms of profitability, and are typically pretty easy to pull off even with other players fighting you for it. However, one variant, Assassination, is blatantly impossible without friends. Not only do you have to deliver each crate individually like in the Merryweather Drop variant, but just spawning them requires killing 6 targets placed randomly around the map, meaning invariably at every corner of the game world. Getting to all targets solo is near impossible within the 15 minute timer, much less going wherever the crates spawn (also random) and getting even one to your nightclub. Here's the catch: any player can kill the targets, and it counts for the whole server, but whoever's killed the most is the only one that gets an exact location for the cargo. Long story short, whoever's in the lead has to rely on other players participating to win, so nobody ever participates. Whenever this mission pops up, the absolute best thing you can do is trigger it, then go do something else for the next 30 minutes.
One of the delivery missions for your Motorcycle Club product has you drop the packages by speedboat on Lake Zancudo. While the optional bonus for fast delivery might make it seems like the best of the delivery missions, this temptation to complete the mission fast works against you, as you are required to go down a rapid running out to sea, with cliffs and beach along the narrow river. It is extremely likely that you will beach the speedboat and be unable to make the delivery at all, even if you resist the temptation of extra cash. The amount of valuable cargo that can be lost on a failed job makes this Rage Quit central.
One particular Smuggler’s Run selling mission has you fly a Mogul for the mission. What’s so bad about it? You have a permanent four-star wanted level, so if you need to land for any reason you WILL get mobbed by cops and NOOSE. In addition, there are two helicopters that persistently chase you in addition to the police helicopters. Did we mention that the Mogul is slow, lacks missiles, and is a large target? Unless you have an assistant to man the gun turret and/or air support from friends, this mission often is summed up as “Take off, get wanted level, spawn enemy choppers, make one or two drops, get shot down, Rage Quit”. And this is being generous and hoping no other players decide to chase you.
Remember the mail van mission for the MC businesses? Meet the "Stolen Animal" Vehicle Recovery security contract in The Contract update. Franklin has you rescuing a monkey from Merryweather in Humane Labs, and the vehicle the monkey is in is slow. Don't forget the waves from Merryweather shooting at you while you are escaping with the monkey in the van. The Merryweather jeeps don't respawn infinitely (they appear in three separate pairs, so that killing the enemies in the first two vehicles spawns the next two, and so on), but outrunning them in the van is all but impossible; your best bet is to get the vehicles to spawn by climbing into the van, then quickly getting back out, taking cover, and killing the enemies on foot. It pays a little more than other contracts, but usually isn't worth the time.
"Asset Seizure" from the ULP bundle of missions. Players have to take down five guarded signal jammers scattered in randomized locations across Los Santos. These can be taken down with stealth, but the moment things go loud, attack helicopters start spawning and shoot super precise machine guns at players. Taking one chopper down provides little respite as another will instantly spawn to take its place. Once the jammers are gone, players have to hijack a van and take it halfway across the map to Blaine County. The van is slow and un-maneuverable and is chased by the aforementioned attack helicopter and mooks in much-faster trucks. If players are lucky, the van will be a relatively fast delivery van. If they're unlucky, it will be a mail van that can barely move up hills.
pissed a lot of players off. Thankfully, there is another bug that lets players escape by stolen helicopter, and clever players can take an armored truck (which can spawn by letting the alarm go off at the bank) down an alternate route to reach the getaway point safely (if more slowly).