derailed mission

Derailed Mission Guide

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If I think back to my childhood, one of my key memories is sitting in front of my TV playing the ‘Wrong Side of the Tracks’ mission from GTA San Andreas and growing increasingly irate as I failed and failed. I tell you this little anecdote for two reasons, the first is that I was far too young to play that game, and my parents should have known better.

The second is that GTA has always been able to through their players into scenarios whereby the events of the game stick in the player’s head for years to come. 

The writing, craziness, and sheer scale of some of these missions really help imprint them on your memory, and so, whenever I play a GTA game or any Rockstar title for that matter, I look out for those missions, the ones that will stick with me.

Funnily enough, even with the updated graphics and scale of GTA 5, I often found the main campaign missions lacking in some way, whether in originality or overall design, I’m not sure. Regardless, I, like many avid GTA fans out there, found the main missions to fall rather flat compared to the franchise’s golden years that saw Vice City and San Andreas lead the way.

However, with all this in mind, I will say that the few missions that I did enjoy not only left an impact but they also made me want more, pushing me into the extended content of GTA 5′s online world whereby the craziness and absurdity of the franchise hit its peak.

One of my favorite missions in the GTA base game is entitled Derailed; however, it doesn’t seem to get quite the level of praise I feel it deserves from fellow gaming writers and critics. Therefore, I think it is only right that I correct this mistake and give the mission the screen time it so deserves. 

So, whether you have come here via your love for the mission or are somehow struggling to progress through it, you have come to the right place as this Derailed Mission guide will take you through Derailed step by step, ensuring to point out some of the highlights along the way. So, what are we waiting for? Let’s go!

Build Up

Vinewood Sign
Vinewood sign. Photo by James Gibson.

As with any mid-game mission in GTA 5, Derailed only begins after the right amount of people have been consequently annoyed by the prior actions of one or more of the protagonists. In this case, the Derailed mission can only be started after the events of The Paleto Score heist.

Having already completed a couple of heists now as a team, Franklin, Trevor, and Michael decide to make their fourth heist a big one, targeting the Blaine County Savings Bank in the small town of Paleto Bay by way of a massive minigun and armored bomb suit.

While extremely dangerous and insanely violent, this mission is one of the more mundane heist missions, requiring the player to simply stand in front of the police as a sort of bullet sponge while your co-conspirators complete the real job of stealing the money.

Paleto Bay Heist

Regardless, this mission ends when the player escapes back to Sandy Shores and divides up the take between the three main parties, quickly splitting up after that with Trevor and Franklin riding away in a utility truck, leaving Michael alone.

Starting the Mission

One would assume that escaping police retribution after gunning down several hundred of their number and somehow surviving without a scratch would be enough excitement for a little while, perhaps an entire lifetime. However, this assumption would be wrong for the craziest member of our protagonist trio. 

Soon after the successful heist’s heat has cooled, Michael finds his way to Trevor’s home, a rather shabby trailer out in Sandy Shores. When Michael arrives and enters said trailer, Trevor is nowhere to be found, but before Michael can gather himself to leave, Ron Jakowski enters the home. 

At this point, we have already met Ron, the loveable CEO of Trevor Phillips industries and resident conspiracy theorist. However, his arrival is unexpected, especially when Trevor is nowhere to be seen. In the homeowner’s absence, Michael and Ron have some witty back in forth for a short while before the crazy train rolls into town in the form of Trevor.

Entering through his door and recognizing that both Michael and Ron are present, Trevor leaves little room for an explanation as he quickly informs the pair that Merryweather Security, one of our adversaries in GTA 5, is moving some mysterious cargo that Trevor wants to get his hands on. 

Merryweather Security
Image from 5MODS

In Brief:

  • Before this mission, the player will have conducted the Paleto Bay heist, robbing the local bank with a minigun and a fully armored suit.
  • The target of this mission is Merrywaether security, a group our trio constantly butt heads with throughout the game and antagonizes to the point of all-out war.
  • Michael must go to the Trevor Phillips residence in Sandy Shores to start this mission.

The Mission

After discussing a brief plan, Trevor and Michael head out to steal this payload. In the beginning, the game places you as Trevor on the back of a Sanchez motorbike, speeding towards the train tracks in Sandy Shores. Here, in a flashback to that aforementioned GTA San Andreas mission, Trevor must use the rocky hillside to speed along beside the train and make the perilous jump onto the moving railcar. 

Trevor Riding on the Train

After landing on the train, Trevor proceeds up the long body of the transport train on the back of his Sanches, only disembarking once he has reached the head of the train.

Here, the player will watch as Trevor hops into the driver’s carriage on the train, throwing the man out of the moving vehicle and proceeding to step on the gas, missing the Merryweather stop in Paleto Bay altogether blasting on into the dessert. 

After this scene, the game perspective shifts, and you are now playing as Michael. The more sensible of the two characters must drive up the river in a boat until the player reaches the train bridge near Cassidy Creek. Here, Michael will see the train that Trevor was supposed to be driving crash head-on with another locomotive, causing mayhem and destruction all around.

While the player initially worries about Trevor, the game shows you that Trevor has already abandoned the train and is perfectly safe. 

Train Crashing
Train crashing. Photo by Photo by James Gibson.

Knowing that his friend is still alive, Michael returns his attention to the mass of fire and wreckage on the train tracks and the myriad of train cars that have now found their way into the creek itself.

The player, still in Michael‘s shoes, must jump into the water and find the Merryweather payload container, blowing the doors off of the unit to liberate the cargo soon after. Switching positions with Michael, Trevor swims up to and enters the boat before fending off myriad Merryweather personnel in the form of helicopters, boats, and very inaccurate snipers.


Once Michael has successfully liberated the cargo from the sunken trailer, both he and Trevor must escape the massive Merryweather Security response in their boat, using their vehicle’s improved speed and the player’s ability to continually load failed missions to their advantage. 

During this ride to freedom, the player is put into Trevor’s shoes and must help Michael steer the boat to safety by eliminating all Merryweather personnel in their way. While this part of the mission may take you a couple of tries, you will eventually understand the pattern the enemy has been programmed to attack in, allowing you to anticipate their movements and attack times.

My top tip here is to take out the snipers as early as possible because, at this stage, they may have thermal scopes, aiding with their shocking aim.

Escaping Merryweather
Escaping Merryweather. Photo by James Gibson.

This battle for freedom will continue for some time until the pair make it out of the creek and the connecting tributary, making it onto open water and eventually losing their Merryweather pursuers thanks to the increased speed of their lighter boat.

The game will then direct the player to steer the boat to shore, landing at a site already equipped with two escape vehicles. However, before the pair part ways, Michael insists on opening the briefcase with the payload inside, only to find an ancient artifact in it. Unaware of the item’s inherent value, Michael suggests that they should give the piece away to Martin Madrazo as an apology. You remember Martin, don’t you?

The drug kingpin had his house destroyed by Michael and Franklin while pursuing his wife’s philandering tennis coach. There was also that small issue of Trevor having kidnapped his wife, Patricia Madrazo, for a short spell. 

Trevor is instantly against such a plan, not wishing to throw away all their hard work and copious near-death experiences just to please some drug cartel leader. However, Michael knows that Martin won’t let their previous slights go without some sort of service or retribution.

Therefore, he insists that they make everything right and gift the artifact to Martin. Trevor is still defiant, however, and will not let the piece go so easily.

Michael, therefore, decides that the only way to convince him is to exchange his services for the heist on the Union Depository, a job Michael had been shooting down for the entire campaign thus far, saying that it was impossible from the get-go. However, Michael now changes his tune, stating that with Franklin’s help, the job could be done. However, he will only do it if Trevor agrees to give the item to Martin. 

Michael Mission End
Michael at the end of the mission. Photo by James Gibson.

Finally getting his wish to rob the Union Depository, Trevor reluctantly agrees in the interest of getting an even bigger score down the line. This allows the pair to split up and go their separate ways, with Michael jetting off to mend fences with Martin. 

Things to Keep in Mind

  • Because Michael decides that they must return the artifact to Martin, this mission ends without either character earning any money, therefore, there is no actual reward for this mission.
  • Even though the characters are effectively stealing from Merryweathersecurity, one can assume that they were involved in something shady that nobody knew about because the incident does not affect their stock price. Therefore, do not short them in the stock market before this mission, as it will not benefit the player.
  • To receive the gold medal for this mission, you must complete the entire quest within 11:30. This will likely require the player to skip all cutscenes. The player must also reach the top Sanchez speed at some point during the mission. Lastly, you must earn the ‘Better than CJ’ objective. This reference to San Andreas requires the player to land on the train using the first jumping opportunity.
Scene from San Andreas
Scene from San Andreas. Photo by James Gibson.

In Brief:

  • Michael and Trevor have already run afoul of Martin before this mission, so Michael decides that to move forward with their plans, the group must ensure that he will not come after them for retribution, therefore risking their future plots.
  • To complete the mission, Trevor and Michael must escape the pursuing Merryweather forces into open water. 
  • This is one of only three missions in which the player can use a thermal scope.

Derailed Mission: FAQs

Question: What did Trevor do to Martin?

Answer: After the two have a massive argument and disagreement, Trevor loses it and proceeds to cut off the cartel boss’ ear and kidnap his wife, Patricia. Later in the game, Trevor and Patricia can be seen to actually get along, prompting Michael to make a Stockholm Syndrome joke.

Question: Can you derail a train normally in GTA 5?

Answer: While you cannot crash a train into another, derailing it in the same manner as Trevor does in the Derailed mission, you can derail trains using sticky bombs. To do this, make your way to the head train car and plant at least five sticky bombs there, and exploding these devices will derail the train.

Question: How do I land on the train with Trevor?

Answer: The rocky outcroppings that the game directs you towards are the easiest ways to jump on the train, as they are specifically designed for this purpose. Once here and jumping, make sure you use your directional controls to steer the Sanchez while in the air, aligning both of your wheels with the train. The player should also release the throttle of the motorbike before jumping; this will ensure you do not ride off of the train upon landing.
So there you go, a detailed guide to one of the best missions in all of GTA 5. Not only does this mission take me back to GTA San Andreas, but it also shows off just how crazy our modern-day characters are and how far the graphics in these games have come. 
I hope this guide has helped you with this mission and, possibly, inspired you to give it another go and perhaps go for those gold medal objectives while you’re at it. Either way, I hope you enjoyed it and to see you again soon. Good luck!

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