As Dusk Falls

Here are the choices I made for Jay that allowed me to get this achievement. I'm not sure if all of them are completely relevant, or if I'm missing anything important, so please feel free to add any additional insight you may have in the comments.

- I dropped Vanessa off in Idaho and reached the boarder alone, not pursued. I didn't freak out at the traffic stop, if that helps. Play it cool, the system will be down.

- Met Forest Ranger. I lied to him, trying to cover my identity. I told him I made a campfire already, that I was lost, that he had my dream job, and that he was mistaken when he confronted me over his suspicions.
When he didn't back down, I made a run for it.

- Pursued by Ranger. I made my first QTE and got up to the top of the waterfall. I tried to make a jump for it, but he stopped me. I had the option to kick his leg out from under him in a QTE, but I didn't want to hurt him, so I purposefully failed the QTE. The Ranger apologized to me and said that he didn't want to see me hurt myself, and that whatever it was that I did, I would have to face it as he held me at gunpoint.

That was when the achievement popped for me. Hope this helps!

This achievement is obtained in the sixth chapter of the game.

It is necessary that at the end of the fifth chapter Vanessa decides to go with Jay to Canada. In the sixth chapter when the two arrive at the police inspection and the same goes to check the license plate of the car, you will have two options, they are "wait for the guard or flee", choose the last one and so when they arrive at the park Vanessa's father will find them with the FBI, the girl will be caught and you will have the option to flee or surrender, choose the second. Choosing the option, Jay will surrender while Vanessa rejects him, at the next checkpoint the achievement will be yours!

Sorry if there are any mistakes in the writing, as English is not my native language, so I had the help of a translator.

In Chapter 6 (Vanessa must be here too) don't do the QTEs as the cops follow Jay and Vanessa and Jay will be arrested.

For a Full and Fast Achievements Guide check the link below:


Timestamps:

00:00 Intro + Useful Information
02:02 Chapter 1: Story
03:49 Chapter 1: Code Breaker + Smooth Criminal Achievements
05:14 Chapter 1: Message Received + Tables Turned + And So It Begins… Achievements
06:32 Chapter 1: Bungled Achievement
07:16 Chapter 1: Cop Out + Point Blank Achievements
08:18 Chapter 2: What’s Your Emergency? Achievement
09:12 Chapter 2: Story
10:08 Chapter 2: Paging Dr. Walker Achievement
10:57 Chapter 2: Keeping The Faith + Second Chance + Lifesaver Achievements
11:56 Chapter 2: Dodged A Bullet + Caught in a Trap Achievements
12:21 Chapter 2: What’s Done is Done + Unforgiveable Achievements
13:32 Chapter 3: Long Arm of the Law
14:01 Chapter 3: Story
14:24 Chapter 3: Resurrection Achievement
14:48 Chapter 3: Take Me Instead + New Dawn + From Dusk ‘til Dawn Achievements
15:59 Chapter 3: Better the Devil You Know Achievement
16:23 Chapter 3: Buried Alive Achievement
16:44 Chapter 3: She’s Coming with Us Achievement
17:18 Chapter 4: Invincible Achievement
17:49 Chapter 4: Story
18:46 Chapter 4: Cabin? What Cabin? + Brothers in Arms + Into The Woods Achievements
19:46 Chapter 4: Trail of Breadcrumbs + Once a Holt + Hands in the Air + No Going Back Achievement
21:19 Chapter 5: Bullseye Achievement
22:04 Chapter 5: Plead the 5th Achievement
22:28 Chapter 5: Story
22:54 Chapter 5: Jailbird Achievement
23:23 Chapter 5: Heart to Heart + Bonnie and Clyde + Runaways Achievements
24:14 Chapter 5: Cuba Libre Achievement
24:58 Chapter 6: Story (Wait for the Cop)
25:43 Chapter 6: Into the Wild + Breaking Bread + Past, Tense + End of the Road? Achievements
26:56 Chapter 6: Almost Made It + Enough is Enough + Stay of Execution
27:47 Chapter 6: You’re On Your Own (Chapter5) + Free Bird + Most Wanted Achievements