Untaxing the Poor Walkthrough in Oblivion Remastered

Participating in the Thieves Guild in The Elder Scrolls IV: Oblivion Remastered is an act of rebellion. It's a choice to reject the rigid Code of Cyrodiil and enter the profession of stealth, deception, and redistributing wealth to those the Empire has forgotten. But whereas the other guilds compensate you with a definite line of quests or linear promotion paths, the Thieves Guild provides none of them. They are independent agents, surviving on talent, reputation, and cunning to establish their utility.

Your initial true test is unwinding the ill-oblivion remastered, your initial official quest that introduces you to the Guild's philosophy, stealing for justice, and not greed. The quest leads you to the hub of the Imperial City, where the poisoned circle that you and the poor are trampled upon by unfair taxes. The quest: burglarize South Watchtower and steal the tax rolls being carried by the infamous Captain Hieronymus Lex.

How to Unlock the Untaxing the Poor Quest

To unlock the Untaxing the Poor quest, one needs to initiate as an established burglar of the light in the Thieves Guild prior to advancing. Merely becoming a guild member is insufficient. Specialty work is only assigned by the Gray Fox organization to personnel who have demonstrated they can make money and not be noticed.

After completing the initiation ceremony with Armand Christophe at the Imperial City Waterfront, you'll do fencing for a minimum of 50 gold's worth of stolen items. "Fencing" is selling your stolen items to a Thieves Guild fence, a black market merchant who buys only and sells only stolen items. If you don't fence it, Armand won't consider you prepared for the first special mission of the Guild.

The easiest way to reach that 50-gold level is by stealing lightly defended stores late at night. The more convenient of these relatively early on is the Red Diamond Jewelry store in the Market District. Wait until after midnight, use your lockpicking skill to break into it, and loot the display cases inside. Jewelry has a decent gold-to-weight ratio and is best suited for easy thieving runs. Once your pockets are full, head north to the city of Bruma and visit Olav’s Tap & Tack. Inside, you’ll find Ongar the World-Weary, the first fence most players will meet in Oblivion Remastered. Sell enough of your stolen loot to meet the 50-gold requirement, then return to the Imperial City Waterfront.

Later at midnight, return to Armand Christophe and choose the "Thieves Guild Special Jobs" option. This will allow Oblivion Untaxing the Poor, beginning your first major mission with the Guild.

Beginning the Heist: Infiltrating the South Watchtower

The Untaxing the Poor quest attempts to reclaim a specific document, the Waterfront Tax Records, that tallies up the discriminatory taxes that the city's poor citizens must pay. They are owned by at least Captain Hieronymus Lex, a zealous order-finder and Thieves Guild-spotter. The documents are hidden in Lex's bedroom within the South Watchtower, located in the Arboretum District of the Imperial City. The complex is under constant surveillance, and day access to it is close to impossible. Stealth and timing are called for in pulling off the heist successfully.

The best time to make the move is late morning or late night, 9 AM to 11 AM or 9 PM to 11 PM. At these times, the lower floor guards start vacating their posts, and the ground floor is left momentarily empty. Take your chance and slip in undetected.

Once inside the tower, stay in crouch and take note of whatever any wandering guards are doing. The interior is narrow with ladders going up to the highest floors on which Hieronymus Lex's room is located. Once you are in Sneak mode, look at your crosshair. The darker it gets, the more undetected you are. Do not move unless you can move unseen, and refrain from bumping into things and creeping right up to sleeping guards.

Stealing the Waterfront Tax Records

The climb to Lex’s quarters is tense and claustrophobic. The South Watchtower’s narrow wooden ladders creak underfoot, and even the smallest sound can wake a nearby guard. If you’re struggling with noise, remove your boots before sneaking further, especially if you’re wearing heavy armor. Even the faintest metallic clink can ruin an otherwise perfect infiltration. When you finally reach the highest level, look to your right. On the desk in Hieronymus Lex's office is a small locked drawer. This is where you stash the Waterfront Tax Records. The lock is fairly difficult, so it would be useful if you have a few spares handy or the ability to cast a security spell.

Open the cabinet, take the records, and do not linger too long. The longer you stay inside the tower, the better the chances of being detected. Retreat quietly, going down the same ladders and patrol lines you memorized while going up. Once out of view, head back to the Imperial City Waterfront at dusk.

Going back to Armand Christophe

As with most of the Thieves Guild encounters, the encounters are at midnight. Wait later and return to Armand Christophe's regular spot at the Imperial City Waterfront. Approach him and provide him with the tax records.

Armand will approve of your work, rewarding you for your ability to sneak and for the fact that you can function under pressure. Completing untaxing the poor oblivion remastered rewards you with an Infamy boost and promotes you to the rank of Footpad in the Thieves Guild, the first step up the ladder to master thief. You are also granted two Infamy points, making you a man who lives outside the Empire's harsh laws.

The History Behind the Job

Unlike most early quests in the game, Oblivion Untaxing the Poor carries moral weight. You’re not just stealing for profit, you’re striking a blow against systemic corruption. Captain Hieronymus Lex, though honorable in his own way, has been exploiting the citizens of the Waterfront by imposing unfair taxes and hoarding the gold meant for Imperial coffers. By stealing the records, you’re both exposing and undermining that corruption.

It's a wonderful primer on the Thieves Guild ideology: they're not thieves, but agents of balance. They desire to ensure that the wealthy and powerful cannot exploit their power to oppress freely, but give poor individuals an opportunity to struggle to survive in a city based on greed.

This ethical dilemma transforms stealing from the rich Oblivion Remastered into one of The Elder Scrolls IV: Oblivion Remastered's greatest faction reveal moments. You not only discover the stealth mechanics, but you are also provided with a purpose for what you're doing. Stealing all the coins, lockpicking all the locks, and lingering behind all the shadows is now part of an epic tale of justice through subversion.

Final Thoughts

Completing Untaxing the Poor Oblivion establishes the tone for the rest of the Thieves Guild questline. It's a sneaky, timely, and morally complicated quest that has players think like actual-life rogues. It's not hack-and-slash, high-damage warfare; it's patience, intelligence, and precision.

Through this initial quest, you become not only a member of the Thieves Guild but also gain insight into the world's social order, where the pauper class has bureaucracy's boot heel on their necks and justice finds its best expression in the shadows.

In the expansive universe of The Elder Scrolls IV: Oblivion Remastered, freeing the poor from oblivion is the ultimate indicator of the game's permissiveness and moral ambiguity. A reminder that sometimes the most heroic thing anyone can do is not kill a Daedra or rescue a city, but merely steal the truth from one who likes to keep it to themselves.