You can get all four Simple Keys in Hollow Knight: Silksong by exploring specific late‑early to mid‑game areas and doing a mix of buying, looting, and a miniboss kill.

Quick Scoop: All 4 Simple Keys

There are four Simple Keys in Silksong, and each one is tied to a clear landmark or event in Pharloom.

1. Bone Bottom – Buy from Pebb

  • Go to Bone Bottom , the main early hub town.
  • Find Pebb , the merchant.
  • Buy the Simple Key from Pebb for 500 Rosaries – it’s pricey early on, so you may want to farm Rosaries first.
  • This is usually the first Simple Key players pick up, since it’s available as soon as you can afford it.

2. Sinner’s Road – Roachkeeper Miniboss

  • Progress through Sinner’s Road , a vertical, tower‑like area you reach after Greymoor or via routes from Songclave.
  • Climb toward the top of the tower , where you’ll encounter the Roachkeeper miniboss.
  • Defeat the Roachkeeper to receive a Simple Key as a guaranteed drop.

3. Songclave / First Shrine – Jubilana’s Key

  • Reach Songclave (also called the First Shrine in some guides).
  • Interact with the bulletin board to start the Wandering Merchant quest – this eventually brings Jubilana into the area.
  • After progressing that quest, talk to Jubilana , who will sell you a Simple Key for Rosaries.
  • This is often considered the “trickier” vendor key because Jubilana doesn’t show up until you trigger her quest.

4. Sands of Karak – Corpse on the Bench

  • Travel to the Sands of Karak , a later‑game desert region reached by heading north from the Blasted Steps.
  • Look for the eastern/rightmost bench in this area.
  • Loot the corpse sitting on that bench to obtain the final Simple Key.
  • This is usually one of the easier keys mechanically, but it’s locked behind game progression to the late areas.

Where You Use Simple Keys (Quick Context)

You asked “how to get” them, but it helps to know why they’re good. Each Simple Key opens a specific lock somewhere in Pharloom, often giving you shortcuts or rewards.

In broad strokes, the four keys are used on:

  • A door near Bone Bottom that links to the Wormways , acting as a fast‑travel shortcut and path toward places like the Chapel of the Wanderer.
  • A lock in Deep Docks , opening up hidden routes and extra rewards.
  • The Green Prince’s cage in Sinner’s Road , freeing a prisoner and unlocking story or reward content.
  • A Rosary room in High Halls , essentially a treasure room packed with currency.

Mini Route Tips (If You’re Stuck)

  • If you’re early game and broke, focus on:
    • Pebb’s key in Bone Bottom once you can scrape together 500 Rosaries.
* Pushing toward **Sinner’s Road** to beat the **Roachkeeper** for a “free” key.
  • If you’re mid‑game:
    • Make sure you’ve triggered the Wandering Merchant board in Songclave so Jubilana actually appears. Players often miss this and think the key is bugged.
  • If you’re late‑mid game:
    • Clear through Blasted Steps into Sands of Karak , then beeline for that eastern bench corpse for your last key.

Simple Keys Snapshot (HTML Table)

[3][7][1] [1][3] [5][3][1] [3][1] [1][3] [8][3] [7][3] [7][3] [8][3][7] [9][3][1] [8][3][1] [9][3][8]
Simple Key How to Get It Area General Use
Key #1 Buy from Pebb for 500 RosariesBone BottomOpens a Wormways shortcut near Bone Bottom
Key #2 Defeat the Roachkeeper minibossSinner’s Road (upper tower)Used on locks like the Green Prince’s cage / shortcuts
Key #3 Complete Wandering Merchant steps and buy from JubilanaSongclave / First ShrineUsed on one of the late‑game doors (e.g., High Halls)
Key #4 Loot corpse on rightmost benchSands of KarakFinal key for remaining locked door(s) and secrets

TL;DR: To get Simple Keys in Silksong, buy one from Pebb in Bone Bottom, beat the Roachkeeper in Sinner’s Road , unlock and purchase from Jubilana in Songclave , and loot the corpse on the eastern bench in Sands of Karak.

Information gathered from public forums or data available on the internet and portrayed here.