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
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

- 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

- 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:
- Move through the first room, dealing with undead or sneaking by.
- Watch for pressure plates—stepping on them sets off traps like arrows.
- 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.
- Keep going through straightforward paths, dodging traps (use Night-Eye to see better).
- 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

- 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 弓 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

- 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.




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