As Dusk Falls

To earn this achievement you need the Holts to lock you and Michelle in the other room, escape your bindings, and then call Vince and request help.

To accomplish this, load up the "Vince Held the Gun" section of the Chapter 2 story tree.

The important decisions which will impact this achievement are as follows:

When given the option to either "Insult Tyler" or "Calmly defy him", wait a few seconds. A third option will appear which says "Crack a joke". Select this option.
After you've been locked in the other room with Michelle, complete the QTE to escape your bindings.

You'll automatically move to the phone and call Dante, earning your achievement.

If you're struggling with any QTE, you can extend your QTE timer in the game options. This affords you a bunch of extra time to get them done without failing.

A video of this achievement can be found in the video below, starting at 0:00.

Michell doesn't have to be shoot at the end of chapter 1. Crack a joke with Vince at the start of Chapter 2. Do the QTEs.

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

Achieved at start of chapter2. Earned during run where Sam is shot and you took the unloaded gun from Tyler and tried shooting him. Crack a joke to get tied up in the back office and then successfully break free of your bindings to complete.