As the game starts, Kenny and Lee will be scavenging for supplies, he’ll climb a ladder and when you try, it’ll break. Look for a Jeep nearby and hook up the tow cable to the front of it and use the wench to pull the Jeep. Climb on top of the Jeep and Kenny will attempt to pull you up to the ledge with him, but drop you.
Your first QTE will start here, a woman will come screeching and, of course, attract walkers. You must decide if you want to put her out of her misery or let the walkers get her, hopefully making your job much easier. Letting the walkers get her gives you more time to loot the drugstore. Kill her or don’t, you will still net the first achievement.
This is a pretty easy and straight-forward chapter; however it will begin with a QTE, so press the buttons as they appear, then move the refrigerator to bar the door and attack the other Walker to get out of the drugstore. Once back at the inn, simply listen to Kenny and Lilly fight, pick your dialogue options and net your achievement.
After dealing with Lilly, head outside and talk to Duck who’s been listening in on your conversation and wants to help. Answer how you want, he’s helping, period. Talk to everyone about the flashlight, then head to the far left of the inn and you should see an 'X' written on the side of one of the rooms with chalk, talk with everyone about the chalk as well. Duck will call you over and say he’s found something, he offers you a high-five, accept or decline, the notification for accepting is pretty awesome.
If you have Carley, you can tell people about your past, you don’t have to, but it can offer some interesting dialogue between Lee and the others.
Examine the mark and push the gate, go all the way to the right and examine the grate in the wall. Head back to Lilly and tell her about the stash, listen to her psychotic rampage until you hear a rustle going on outside.
A QTE will soon follow, react as follows:
1) Aim and kill the first bandit, if you have Carley, she’ll take him out instead.
2) Kenny will give you a rifle, go to the left and take out the bandits by the dumpsters. If the edges of the screen start to go red, press B to make Lee go back behind the RV before you get shot. Don’t let them go too far to the left, or they may get behind you.
3) After shooting the bandits, Doug/Carley and Ben are safe to get in the RV. You must now deal with the right side. Do the same thing as before.
4) After shooting all three bandits, Clementine runs over to Lee and safely makes it into the RV. However, Katjaa and Duck will get attacked by a walker - quickly kill it to save them. If you’re too slow, Kenny will save them instead.
5) If you have Carley with you, she’ll assist you. All you need to do is stay on the right side, and kill the four walkers. If you have Doug, you pretty much must switch back and forth to stop the walkers from getting too close.
Once you’ve taken care of the walkers, the group will then get into a heated argument with Lilly on the RV as to who was helping the bandits, choose your dialogue. Eventually Kenny will run into a walker and pull over to fix the RV and the group will step out and continue their shouting match. Lilly will keep throwing accusations around, if you have Carley with you…. Well, I’ll leave what happens out. Choose whatever dialogue options you want after the event.
Katjaa will call you over and let you in on a horrible realisation - Duck was bitten during the attack at the inn. Katjaa and Kenny ask you to tell Clem, choose your dialogue. Shortly after a QTE will occur, just mash 
, even if you fail you’ll live.
When you exit the RV, check on Duck, Katjaa will ask you to find him water, this is optional but will help vastly improve your relationship with Kenny and Katjaa. Head into the RV to grab the pencil, you’ll need it later.
Optional for Duck: Head into the boxcar to the left of Ben, it’s the only other one you can access; there’s a water bottle in here for you, grab this and head over to Katjaa.
Climb up the ladder on the main train car and open the second compartment and grab a tool, then head over to the door to the engineers cabin and open it with the tool.
Kenny will tell you that you need to get the train moving, there will be a notepad nearby with an imprint on it but is too faded, did you ever do ‘rubbings’ in elementary school? Use the pencil on the notepad.
Head to the many switches and levers in the cabin and follow what the instructions on the notepad say and after working through all of the switches head to the door near the front of the cabin.
Optional for Duck: Around the front of the train you’ll notice a walker stuck in a car, head down and you’ll see he’s stuck. Release the seatbelt and then slam the door against its head, killing it. Grab the animal crackers and give them to Katjaa.
Head back up to where you grabbed the tool to get into the engineers cabin and open the first compartment, there’s a switch in here, turn it left and then right. Kenny will then talk with you, say what you want. Head into the cabin and pull the throttle, you’ll learn that the main car is still attached to the wreckage behind you.
Go to the second car, the one with the water bottle, and there should be a map as well, take that. Head through the open door to the back of the train and continue around the car, use whatever tool to remove the pin attaching the cars and head back to Kenny. There’s a chance for various conversations before pulling the throttle, chat with people if you want.
After pulling the throttle, answer Chuck how you like, use the rag to clean up the blood and then head to the engineer’s cabin to get Kenny to stop the train. You can do this in many ways, through kindness or aggression, choose whichever you prefer (stay silent for all for an Easter Egg).
You’ll then need to make a tough decision, I won’t spoil it, but I’m sure you can guess what that is, decide what to do and respond to Clem however you wish.
After the event, talk with Clem and she’ll tell you Chuck has said some disturbing things, head to the very front of the train to confront him. After the conversation, head to the second car and teach Clem to shoot, after that cut her hair with the scissors in Chucks bag.
Grab the whiskey and head back to Chuck, give it to him and tell Kenny, who will then move so you can get the map. Then talk to Clem about Savannah. The train will then stop and you’ll get the achievement
You’ll then meet Omid and Christa. Respond to their questions how you like, talk with everyone to see how they are doing, after which head towards the station in the distance. Clem will then decide to join you and help if she can.
When you get to the station, Clem will try to open the door, look up and you’ll see a spot where she can fit, boost her up and she’ll unlock the door for you. Clem will hold the door open and you need to find something to prop it open with, there’s a timer but if it runs out you won’t die, so don’t worry about it. There should be a block or something nearby that can be used to prop the door open.
There’s a blowtorch on the other side of the gate inside and another locked door, do the same thing you did before, send Clem over. This will start a QTE, here's what to do:
1) Grab the door prop and beat the Walker with it.
2) Lee will get grabbed, enter the commands that appear.
3) Grab the key from Clem and use it to unlock the door.
4) Kill the walker.
Christa will come running to see what happened, respond how you want and then grab the blowtorch and return to the group near the train. Talk to Omid and join him on top of the bridge, there should be some tape near one of the trucks. Attempt to use the blowtorch on the tanker, Lee will notice there’s a leak in the line; use the tape to seal it. The tanker will begin to fail, but stop, dangle Omid and have him cut the last bit.
Push the blowtorch over the edge to set the leaking oil ablaze, you now have to get down and the only way is to jump, convince Omid to jump with you (or not). Lee lands safely while Omid slams into the ground, Christa will jump off to help him and you must decide who to pull up.
The rest is just scenes and dialogue options, just choose whatever you like
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