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.
Preparation
Character Skills
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Sneak: Aim for 50+ (75+ is better) to stay hidden. Higher perks make it easier.
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Security: You’ll need to pick some tough locks, so get this to at least Adept.
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Acrobatics: Helps with jumping and moving through tricky spots.
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Illusion: Spells like Invisibility or Chameleon (or potions) make stealth a breeze.
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Marksman: You’ll need to nail a precise shot with the Arrow of Extrication.
Equipment
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Lockpicks: Bring at least 10. Hard locks can eat through them if you’re rusty.
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Bow and Arrows: Grab any bow for the Arrow of Extrication; pack extra arrows for practice.
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Potions/Scrolls:
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Stock up on Invisibility potions (5 or more), plus some for health and magicka.
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Chameleon or Night-Eye potions or gear help with sneaking and seeing in the dark.
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Light Armor or Clothes: Go for stuff like Black Hand Robes or enchanted gear to move quietly.
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Nocturnal’s Skeleton Key: If you did Nocturnal’s quest, this lockpick never breaks.
Inventory
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Clear space for the Boots of Springheel Jak and other quest items.
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Save in a new slot before you start.
Optional
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Do the quest at night in-game for fewer guards wandering around.
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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
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Location: Ganredhel’s house in Cheydinhal.
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Objective: Get the quest and gear from the Gray Fox.
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Details:
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The Gray Fox lays out the plan: steal an Elder Scroll from the Imperial Palace. He hands over:
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Boots of Springheel Jak (boosts Acrobatics by 50—use them for jumps if you need to).
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Arrow of Extrication (you’ll need this later).
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He tells you to activate the Glass of Time in the Palace Arboretum to get started.
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Tip: Only equip the Boots when you need them to keep them in one piece.
Step 2: Activate the Glass of Time
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Location: Imperial Palace, Arboretum District (southeast corner).
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Objective: Flip the switch on the Glass of Time to unlock the Old Way.
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Details:
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Head to the Arboretum in the Imperial City.
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Find the Sewer Entrance (a grate marked on your map).
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Go into the sewer, find the Glass of Time (big glowing crystal), and activate it.
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Tips:
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The sewers have weak enemies like rats. Clear them if they’re in your way.
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No guards here, so you don’t need to sneak yet.
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Save once you’ve activated it.
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Step 3: Infiltrate the Imperial Palace
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Location: Imperial Palace, Palace District.
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Objective: Sneak into the Palace to get to the Elder Scroll.
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Details:
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Walk or fast-travel to the Palace District.
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Enter the Imperial Palace through the main door.
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Start sneaking right away to dodge the guards.
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Make your way to the Elder Council Chambers (follow the quest marker).
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Key Part: You need a key to get in:
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Option 1: Swipe the Imperial Palace Key off a guard (needs good Sneak or Invisibility).
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Option 2: Pick the Hard lock on the door (save first; it’s tricky).
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Get into the Elder Council Chambers.
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Tips:
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Invisibility or Chameleon makes guards way easier to avoid. Stick to shadows.
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Guards follow set paths—wait for them to turn before moving.
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Save often. If you get spotted, reload or leg it to reset the guards.
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Getting caught can mess up the Thieves Guild’s “no killing” rule.
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Step 4: Access the Old Way
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Location: Elder Council Chambers.
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Objective: Find the secret entrance to the Old Way, an Ayleid ruin.
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Details:
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In the Chambers, find the central pillar (big column in the middle).
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Activate it to open a hidden door to the Old Way.
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Head into the Old Way, a creepy dungeon with Ayleid vibes.
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Tips:
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There might be a guard or two in the Chambers—sneak or go invisible.
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Save before entering the Old Way; it’s a rough place.
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Step 5: Navigate the Old Way
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Location: Old Way (Ayleid ruin).
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Objective: Get to the Hall of Epochs for the Arrow of Extrication part.
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Details:
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The Old Way is a maze with:
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Enemies: Undead like skeletons and wraiths, plus traps like pressure plates and blades.
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Puzzles: Ayleid stuff like push blocks and rotating walls.
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Path:
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Move through the first room, dealing with undead or sneaking by.
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Watch for pressure plates—stepping on them sets off traps like arrows.
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In the next area, find a push block (usually high on a wall, glowing a bit).
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Hit it to open a door or move a wall.
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Keep going through straightforward paths, dodging traps (use Night-Eye to see better).
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Reach the Hall of Epochs, a big room with a locked gate.
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Key Part: You’ll need the Arrow of Extrication to open the gate, but you need the right spot to shoot from.
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Tips:
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Sneak past enemies to save health and gear.
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Use Restore Health potions if traps or enemies hit you.
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Save before traps or puzzles—screw-ups can hurt.
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If you’re low level (under 15), the enemies might be brutal. Level up first if needed.
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Step 6: Use the Arrow of Extrication
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Location: Hall of Epochs, Old Way.
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Objective: Shoot the Arrow of Extrication into a keyhole to unlock the gate.
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Details:
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In the Hall of Epochs, spot a statue with a glowing keyhole (high on the far wall).
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Find the shooting platform (a ledge across from the keyhole).
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Equip your 弓 and the Arrow of Extrication (you only get one, so don’t mess up).
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Line up your shot and fire at the keyhole. If it hits, the gate opens.
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If you miss, grab the arrow from the floor near the statue and try again.
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Go through the gate.
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Tips:
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Save before you shoot. Missing sucks.
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High Marksman skill helps, or use aim assist if you’re on console.
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Practice shooting elsewhere if you’re not sure about arrow drop.
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The keyhole’s tiny—take your time.
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Step 7: Steal the Elder Scroll
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Location: Imperial Library, reached through the Old Way.
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Objective: Grab the Elder Scroll from the Library.
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Details:
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After the gate, follow the path to a secret entrance into the Imperial Library.
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Sneak past Blind Moth Priests (monks guarding the scrolls).
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Find the Elder Scroll (glowing on a pedestal or table, marked by the quest).
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Pick it up—no locks or traps, just grab it.
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Tips:
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The priests are blind but hear noise or feel you bump them. Sneak slowly and steer clear.
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Invisibility or Chameleon lets you skip the hassle.
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Save before entering the Library in case you get caught.
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Step 8: Escape the Imperial Palace
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Location: Imperial Library to Palace exit.
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Objective: Get out without getting nabbed.
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Details:
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After grabbing the Elder Scroll, a secret passage opens (look for a hidden door or lever).
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Follow it to the Palace Sewers or another exit path.
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Move through the sewers (watch for rats or minor enemies) until you hit an outside grate.
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Exit to the Imperial City.
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Tips:
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Guards might be on edge—sneak or go invisible to avoid them.
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Use the Boots of Springheel Jak for jumps in the sewers if your Acrobatics is weak.
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Save after leaving the Library to avoid redoing the stealth part.
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Step 9: Deliver the Elder Scroll
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Location: Gray Fox’s spot (Ganredhel’s house, Cheydinhal).
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Objective: Give the Elder Scroll to the Gray Fox.
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Details:
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Fast-travel to Cheydinhal and head to Ganredhel’s house.
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Talk to the Gray Fox and hand over the Elder Scroll.
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He spills his real identity and hooks you up with:
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Guildmaster Rank in the Thieves Guild.
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Gray Cowl of Nocturnal (awesome stealth gear).
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The quest wraps up, and you get access to the Thieves Guild hideout in the Imperial City Waterfront.
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Tips:
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The Gray Cowl gives a huge Sneak boost (+25) and a cool bounty trick (bounty goes to the “Gray Fox,” not you).
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Save after finishing to lock in your progress.
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Additional Tips and Troubleshooting
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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).
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Stealth is Everything: Getting spotted by guards or priests can tank the quest. Focus on Sneak and Invisibility.
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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).
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Arrow of Extrication Glitch: If the arrow doesn’t work, reload and retry. Make sure you’re aiming right at the keyhole.
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Low-Level Problems: Below level 10, the Old Way’s enemies can wreck you. Level up or bring good gear/potions.
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Inventory Space: The Elder Scroll doesn’t weigh anything, but make room for the Gray Cowl reward.
Rewards
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Gray Cowl of Nocturnal: +25 Sneak, +10 Detect Life, +50 Fortify Sneak (gives you a “Gray Fox” alias for bounties).
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Guildmaster Rank: Unlocks the Thieves Guild hideout, better fences, and guild perks.
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Boots of Springheel Jak: Keep them if you don’t use them in the escape (your call).
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Story Payoff: The quest spills the Gray Fox’s secrets and wraps up the Thieves Guild arc.
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