---
title: "Meaning & Key Takeaway of: When shall we break into the jail, then?\"…"
description: "\"“When shall we break into the jail, then?\" John asked. \"Midnight. The guard changes then, and you'll fair certain look less conspicuous in that crowd.\"..."
image: "https://sms4smile.com/quotes/i/13f/a-c-gaughen-18759_took-drink_when-shall-we-break-into-the-jail-then-j_2557908.jpg"
---

#  When shall we break into the jail, then?" John asked…

![“When shall we break into the jail, then?&quot; John asked. &quot;Midnight. The guard changes then, and you'll fair certain look less conspicuous in that crowd.&quot; &quot;So you think I look like a guard? I'll take that nicely.&quot; He took a drink of his beer, his eyes shining at me over the brim. I flicked my eyes…” quote by A.C. Gaughen](https://sms4smile.com/quotes/i/13f/a-c-gaughen-18759_took-drink_when-shall-we-break-into-the-jail-then-j_2557908.jpg)   [Download](https://sms4smile.com/quotes/i/13f/a-c-gaughen-18759_took-drink_when-shall-we-break-into-the-jail-then-j_2557908.jpg) [Open image](https://sms4smile.com/quotes/i/13f/a-c-gaughen-18759_took-drink_when-shall-we-break-into-the-jail-then-j_2557908.jpg)

> ““When shall we break into the jail, then?" John asked. "Midnight. The guard changes then, and you'll fair certain look less conspicuous in that crowd." "So you think I look like a guard? I'll take that nicely." He took a drink of his beer, his eyes shining at me over the brim. I flicked my eyes over him. "Brutish and stupid? Yes, you look quite like a guard.””

[A.C. Gaughen](https://sms4smile.com/quotes/author/a-c-gaughen/)

## About This Quote

This interpretation was drafted with AI assistance. It is one reading of the quote, not the author's own explanation.

A character plans a covert entry at midnight, using disguise and bravado to mask fear.

**In simple terms:** Clever timing and disguise aid risky plans.

Key Takeaway

Use timing and confidence in dangerous tasks.

Themes

strategy disguise risk

Mood

tense dark

Type

narrative dramatic

When to use this quote

- Heist
- nighttime operation
- espionage

Key Concepts

Psychology of deception tactical planning

Questions to Reflect On

- What are the ethical limits of deception?
- How does fear influence bold actions?

A Different Perspective

Disguise can fail if overconfidence shows.

★ ★ ★ ★ ★   No ratings yet

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