The Ultimate Heist in The Elder Scrolls IV: Oblivion is the toughest quest you’ll face in the Thieves Guild storyline. It’s a beast of a mission that wraps up the guild’s arc with a bang, tasking you with snagging an Elder Scroll from the heavily guarded Imperial Palace. This guide breaks it down step by step in a straightforward way, covering prep, execution, and tips to dodge the many ways this quest can trip you up.

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Preparation

Get your character ready before diving in—this quest isn’t forgiving:

Character Skills

  • Sneak: Aim for 50+ (75+ is better) to stay hidden. Higher perks make it easier.
  • Security: You’ll need to pick some tough locks, so get this to at least Adept.
  • Acrobatics: Helps with jumping and moving through tricky spots.
  • Illusion: Spells like Invisibility or Chameleon (or potions) make stealth a breeze.
  • Marksman: You’ll need to nail a precise shot with the Arrow of Extrication.

Equipment

  • Lockpicks: Bring at least 10. Hard locks can eat through them if you’re rusty.
  • Bow and Arrows: Grab any bow for the Arrow of Extrication; pack extra arrows for practice.
  • Potions/Scrolls:
    • Stock up on Invisibility potions (5 or more), plus some for health and magicka.
    • Chameleon or Night-Eye potions or gear help with sneaking and seeing in the dark.
  • Light Armor or Clothes: Go for stuff like Black Hand Robes or enchanted gear to move quietly.
  • Nocturnal’s Skeleton Key: If you did Nocturnal’s quest, this lockpick never breaks.

Inventory

  • Clear space for the Boots of Springheel Jak and other quest items.
  • Save in a new slot before you start.

Optional

  • Do the quest at night in-game for fewer guards wandering around.
  • If your Sneak is low, grind it by sneaking in busy spots like the Imperial City.

Quest Walkthrough: Step-by-Step

Step 1: Speak to the Gray Fox

Oblivion Remastered Epochs Puzzle Steal Elder Scro

  • Location: Ganredhel’s house in Cheydinhal.
  • Objective: Get the quest and gear from the Gray Fox.
  • Details:
    • The Gray Fox lays out the plan: steal an Elder Scroll from the Imperial Palace. He hands over:
      • Boots of Springheel Jak (boosts Acrobatics by 50—use them for jumps if you need to).
      • Arrow of Extrication (you’ll need this later).
    • He tells you to activate the Glass of Time in the Palace Arboretum to get started.
  • Tip: Only equip the Boots when you need them to keep them in one piece.

Step 2: Activate the Glass of Time

  • Location: Imperial Palace, Arboretum District (southeast corner).
  • Objective: Flip the switch on the Glass of Time to unlock the Old Way.
  • Details:
    • Head to the Arboretum in the Imperial City.
    • Find the Sewer Entrance (a grate marked on your map).
    • Go into the sewer, find the Glass of Time (big glowing crystal), and activate it.
  • Tips:
    • The sewers have weak enemies like rats. Clear them if they’re in your way.
    • No guards here, so you don’t need to sneak yet.
    • Save once you’ve activated it.

Step 3: Infiltrate the Imperial Palace

  • Location: Imperial Palace, Palace District.
  • Objective: Sneak into the Palace to get to the Elder Scroll.
  • Details:
    • Walk or fast-travel to the Palace District.
    • Enter the Imperial Palace through the main door.
    • Start sneaking right away to dodge the guards.
    • Make your way to the Elder Council Chambers (follow the quest marker).
    • Key Part: You need a key to get in:
      • Option 1: Swipe the Imperial Palace Key off a guard (needs good Sneak or Invisibility).
      • Option 2: Pick the Hard lock on the door (save first; it’s tricky).
    • Get into the Elder Council Chambers.
  • Tips:
    • Invisibility or Chameleon makes guards way easier to avoid. Stick to shadows.
    • Guards follow set paths—wait for them to turn before moving.
    • Save often. If you get spotted, reload or leg it to reset the guards.
    • Getting caught can mess up the Thieves Guild’s “no killing” rule.

Step 4: Access the Old Way

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  • Location: Elder Council Chambers.
  • Objective: Find the secret entrance to the Old Way, an Ayleid ruin.
  • Details:
    • In the Chambers, find the central pillar (big column in the middle).
    • Activate it to open a hidden door to the Old Way.
    • Head into the Old Way, a creepy dungeon with Ayleid vibes.
  • Tips:
    • There might be a guard or two in the Chambers—sneak or go invisible.
    • Save before entering the Old Way; it’s a rough place.

Step 5: Navigate the Old Way

  • Location: Old Way (Ayleid ruin).
  • Objective: Get to the Hall of Epochs for the Arrow of Extrication part.
  • Details:
    • The Old Way is a maze with:
      • Enemies: Undead like skeletons and wraiths, plus traps like pressure plates and blades.
      • Puzzles: Ayleid stuff like push blocks and rotating walls.
    • Path:
      1. Move through the first room, dealing with undead or sneaking by.
      2. Watch for pressure plates—stepping on them sets off traps like arrows.
      3. In the next area, find a push block (usually high on a wall, glowing a bit).
        • Hit it to open a door or move a wall.
      4. Keep going through straightforward paths, dodging traps (use Night-Eye to see better).
      5. Reach the Hall of Epochs, a big room with a locked gate.
    • Key Part: You’ll need the Arrow of Extrication to open the gate, but you need the right spot to shoot from.
  • Tips:
    • Sneak past enemies to save health and gear.
    • Use Restore Health potions if traps or enemies hit you.
    • Save before traps or puzzles—screw-ups can hurt.
    • If you’re low level (under 15), the enemies might be brutal. Level up first if needed.

Step 6: Use the Arrow of Extrication

The Ultimate Heist Arrow Of Extrication

  • Location: Hall of Epochs, Old Way.
  • Objective: Shoot the Arrow of Extrication into a keyhole to unlock the gate.
  • Details:
    • In the Hall of Epochs, spot a statue with a glowing keyhole (high on the far wall).
    • Find the shooting platform (a ledge across from the keyhole).
    • Equip your and the Arrow of Extrication (you only get one, so don’t mess up).
    • Line up your shot and fire at the keyhole. If it hits, the gate opens.
    • If you miss, grab the arrow from the floor near the statue and try again.
    • Go through the gate.
  • Tips:
    • Save before you shoot. Missing sucks.
    • High Marksman skill helps, or use aim assist if you’re on console.
    • Practice shooting elsewhere if you’re not sure about arrow drop.
    • The keyhole’s tiny—take your time.

Step 7: Steal the Elder Scroll

  • Location: Imperial Library, reached through the Old Way.
  • Objective: Grab the Elder Scroll from the Library.
  • Details:
    • After the gate, follow the path to a secret entrance into the Imperial Library.
    • Sneak past Blind Moth Priests (monks guarding the scrolls).
    • Find the Elder Scroll (glowing on a pedestal or table, marked by the quest).
    • Pick it up—no locks or traps, just grab it.
  • Tips:
    • The priests are blind but hear noise or feel you bump them. Sneak slowly and steer clear.
    • Invisibility or Chameleon lets you skip the hassle.
    • Save before entering the Library in case you get caught.

Step 8: Escape the Imperial Palace

The Ultimate Heist

  • Location: Imperial Library to Palace exit.
  • Objective: Get out without getting nabbed.
  • Details:
    • After grabbing the Elder Scroll, a secret passage opens (look for a hidden door or lever).
    • Follow it to the Palace Sewers or another exit path.
    • Move through the sewers (watch for rats or minor enemies) until you hit an outside grate.
    • Exit to the Imperial City.
  • Tips:
    • Guards might be on edge—sneak or go invisible to avoid them.
    • Use the Boots of Springheel Jak for jumps in the sewers if your Acrobatics is weak.
    • Save after leaving the Library to avoid redoing the stealth part.

Step 9: Deliver the Elder Scroll

  • Location: Gray Fox’s spot (Ganredhel’s house, Cheydinhal).
  • Objective: Give the Elder Scroll to the Gray Fox.
  • Details:
    • Fast-travel to Cheydinhal and head to Ganredhel’s house.
    • Talk to the Gray Fox and hand over the Elder Scroll.
    • He spills his real identity and hooks you up with:
      • Guildmaster Rank in the Thieves Guild.
      • Gray Cowl of Nocturnal (awesome stealth gear).
    • The quest wraps up, and you get access to the Thieves Guild hideout in the Imperial City Waterfront.
  • Tips:
    • The Gray Cowl gives a huge Sneak boost (+25) and a cool bounty trick (bounty goes to the “Gray Fox,” not you).
    • Save after finishing to lock in your progress.

Additional Tips and Troubleshooting

  • Save All the Time: This quest is long and brutal. Save at every big step (after the Glass of Time, before the Old Way, before the arrow shot).
  • Stealth is Everything: Getting spotted by guards or priests can tank the quest. Focus on Sneak and Invisibility.
  • No Killing: Taking out guards, priests, or enemies breaks Thieves Guild rules and can lock you out. Stick to non-lethal moves (sneak, paralyze, or bolt).
  • Arrow of Extrication Glitch: If the arrow doesn’t work, reload and retry. Make sure you’re aiming right at the keyhole.
  • Low-Level Problems: Below level 10, the Old Way’s enemies can wreck you. Level up or bring good gear/potions.
  • Inventory Space: The Elder Scroll doesn’t weigh anything, but make room for the Gray Cowl reward.

Rewards

  • Gray Cowl of Nocturnal: +25 Sneak, +10 Detect Life, +50 Fortify Sneak (gives you a “Gray Fox” alias for bounties).
  • Guildmaster Rank: Unlocks the Thieves Guild hideout, better fences, and guild perks.
  • Boots of Springheel Jak: Keep them if you don’t use them in the escape (your call).
  • Story Payoff: The quest spills the Gray Fox’s secrets and wraps up the Thieves Guild arc.