Skyrim With Friends Like These: Complete Quest Guide & Walkthrough

The Thieves Guild questline in Skyrim is one of the most engaging story arcs in the game, and “With Friends Like These” serves as the gateway into this shadowy world. This quest triggers early in your Guild journey and sets you on a path to rebuild the organization from the ground up. Whether you’re a seasoned Dragonborn or picking up the game for the first time, understanding how this quest flows and what it demands will save you hours of frustration. This guide walks you through every step, from the initial meeting with Delvin and Vex to completing the sprawling restoration quests that follow. You’ll learn the mechanics, avoid common pitfalls, and maximize the rewards that make the Guild questline so worthwhile.

Overview Of The With Friends Like These Quest

Quest Location And How To Start

“With Friends Like These” kicks off inside the Thieves Guild headquarters, the Flagon, located beneath Riften. You won’t stumble into this quest by accident: it becomes available once you’ve completed the prerequisite quests “A Chance Arrangement” and “Taking Care of Business.” If you haven’t joined the Guild yet, your first step is to commit a theft in Riften or accept Brynjolf’s initial fence job. Once you’re inducted and complete those two opening jobs, Brynjolf will direct you to speak with Delvin and Vex in the Flagon’s main chamber.

The Flagon itself is accessed through the sewers, you’ll need to go through the Ratway, which connects from the Riften Fisheries. It’s straightforward but worth noting that the path involves navigating past some lower-level bandits and creatures. On your first visit as a Guild member, there’s no combat, so the route is purely navigational.

Quest Objectives And Rewards

The core objective of “With Friends Like These” is simple on the surface: complete at least five jobs assigned by Delvin and Vex to earn their confidence and trust. But, the quest doesn’t end there. Once you’ve finished those five jobs, the real work begins, you’ll need to complete additional restoration quests to expand the Guild’s influence across Skyrim‘s major regions.

Upon completing “With Friends Like These” itself, you’ll receive the Thieves Guild quests that unlock the path to eventually becoming the Guild leader. More immediately, you gain access to better fence prices, additional Guild perks, and the ability to expand Guild operations. The monetary rewards from completing the five jobs total around 500–600 gold, plus whatever loot you pick up during the job missions themselves. The real payoff, though, is gaining access to the Guild’s network of contacts and the Thieves Guild armor set, which provides bonuses to lockpicking and pickpocketing that stack nicely with appropriate perks.

Meeting Delvin And Vex In The Thieves Guild

Understanding The Thieves Guild Questline Connection

Delvin and Vex are the two lieutenants under Brynjolf, and they control the day-to-day operations of what remains of the Thieves Guild. By the time you meet them, the Guild has fallen into decline, its influence diminished across Skyrim’s cities. Delvin handles operations in the east (Windhelm, Markarth), while Vex oversees the west (Solitude, Whiterun). Understanding this geographic split matters because it determines which jobs you’ll receive and where you’ll be working.

The questline progression is straightforward: earn their trust through jobs → complete restoration quests → expand Guild influence → unlock the path to leadership. “With Friends Like These” sits at the beginning of this chain, and its completion opens the door to the expansion quests that feel less like fetch quests and more like genuine story-driven missions.

Initial Conversation And Quest Requirements

When you first speak to Delvin and Vex in the Flagon, they’re skeptical of you. They explain that the Guild needs reliable people willing to do actual work, not just talk. This leads to their request: complete five jobs, a mix of steals, burglaries, and other criminal enterprises, and come back to them. You don’t need to complete all five jobs in a single session, though some players prefer to knock them out quickly.

The jobs Delvin and Vex assign are from the general Thieves Guild radial pool. This means you might receive different jobs than another player, one run might include stealing a Dwemer artifact, while another involves pickpocketing a specific NPC. The flexibility is good for replayability but means there’s no single “optimal” path. What matters is that you understand the quest type you’re doing (theft vs. burglary) so you prepare accordingly. A burglary requires you to crack safes and avoid detection: a theft might be as simple as grabbing an item off a table when no one’s looking.

Locating And Completing Job Quests

Types Of Job Quests Available

The five jobs you’ll complete fall into distinct categories, each with its own mechanical demands and strategies:

• Theft jobs: Steal a specific item and bring it back. These are straightforward but require pickpocketing skill or lock-breaking if the item is in a container. Bounties are a real risk if you’re caught.
• Burglary jobs: Break into a building, crack a safe, and steal the contents. These demand higher Lockpicking skill and reward more gold than simple thefts.
• Pickpocketing jobs: Steal a item directly from an NPC without being caught. These test your Pickpocket skill and positioning.
• Raiding jobs: Enter a location, defeat enemies, and steal a specific item. These are less about stealth and more about combat readiness.
• Bounty collection jobs: Locate a target and retrieve a debt or item. These sometimes involve persuasion or intimidation depending on the NPC.

The game assigns jobs randomly, so your exact progression will vary. But, the difficulty scaling is forgiving, the game won’t assign jobs you’re clearly unprepared for.

Strategic Tips For Each Job Category

For theft jobs, your best approach is to case the location first. Visit during daytime when there are witnesses, identify exactly where the target item is, then return at night when foot traffic is lower. Invest in the Pickpocket perk “Skydancer’s Folly” (requires 50 Pickpocket) if the item is on an NPC, as it increases your success rate significantly.

Burglary jobs are best tackled with a strong Lockpicking level, aim for at least 40 Lockpicking before attempting these if you want a seamless process. Bring lots of lockpicks (you can buy them from general goods vendors or steal them). Alternatively, if your Lockpicking is weak, search guard towers and Guard Barracks for free picks. Stealth is essential: use Invisibility potions or spells if you’re spotted.

For pickpocketing jobs, position yourself behind the target NPC and ensure you’re in a location with good lighting and positioning angles. Use Invisibility potions before attempting the steal, it’s not cheating, it’s preparation. Your target might carry keys, weapons, or jewelry: aim for lighter items if your Pickpocket skill is below 50.

Raiding jobs require different preparation entirely. You’re walking into enemy territory, so enchanted weapons (fire, frost, or shock damage) and appropriate resistances help. Stealth is optional here: you might breeze through with a sword and shield build. Just watch for traps, many bandit lairs and Falmer dungeons have pressure plates and tripwires.

For bounty collection jobs, talk to the target first. Sometimes you can intimidate or persuade them into handing over the debt without violence. If that fails, combat is on the table. These jobs reward well because they often involve difficult NPCs.

Restoring The Thieves Guild To Its Former Glory

Guild Expansion Quest Prerequisites

Once you’ve completed those initial five jobs and reported back to Delvin and Vex, “With Friends Like These” technically concludes, but it opens the floodgates to the real meat of the Guild questline: the restoration quests. These are larger, story-driven missions that take the Guild from scattered remnants to a functional criminal enterprise once again.

The restoration quests are divided by region: Whiterun, Solitude, Markarth, and Windhelm. Each region has its own questline that involves completing a specific number of jobs (around 5–7 per region) before unlocking the restoration quest itself. Delvin and Vex will tell you which regions are available and hand out jobs accordingly. The prerequisite isn’t complicated, it’s just “do the work”, but it’s a time investment.

One important detail: you can tackle regions in any order. There’s no level requirement either, though the jobs in each region scale somewhat to the city’s overall difficulty. Solitude jobs, for instance, tend to be slightly trickier than Whiterun jobs because Solitude’s guards are more alert.

Rebuilding Across Skyrim’s Regions

Each region’s restoration quest follows a similar pattern: you’ll be tasked with retrieving a valuable item or completing a specific crime that proves the Guild’s worth to the local power structure. The Whiterun restoration involves intimidating Maven Black-Briar into backing Guild operations. The Solitude restoration asks you to steal from the Blue Palace. Markarth requires you to complete a job for the Forsworn. Windhelm has you working with Ulfric Stormcloak’s regime.

These quests have genuine consequences and story beats. They’re not repetitive fetch tasks, each feels distinct and tied to Skyrim’s political landscape. Completing all four restorations unlocks the path to becoming Guildmaster, but even stopping after one or two provides meaningful progression and ongoing income from radial guild jobs.

The restoration quests also reward you with jewelry, gems, and enchanted items that fence for solid gold. A single restoration quest might net you 500–800 gold in loot alone, plus the gold rewards from prerequisite jobs. Over the course of completing all restoration quests, you’re looking at 5,000–7,000 gold total, not counting crafting materials and equipment upgrades.

Common Challenges And Troubleshooting

Quest Bugs And How To Resolve Them

Skyrim’s age means bugs are still present, and the Thieves Guild questline isn’t immune. One common issue is quest stages not advancing after completing objectives. If you’ve finished a job but the quest marker won’t clear and Delvin or Vex won’t acknowledge your completion, try these steps:

1. Fast-travel to a different location, then return to the Flagon.
2. Wait 24 in-game hours in a populated area (like an inn) to allow quest updates to process.
3. Reload a save from before the job started and retry (only if the above doesn’t work).
4. If the quest remains stuck, check the console (PC) and type setstage tg08 200 to force the quest to the next stage (replace the stage number as needed).

Another issue: sometimes a stolen item won’t register as “stolen” if you pickpocketed it from a dead body instead of a living NPC, or if the item respawned. Double-check your inventory to ensure you actually have the target item before returning to the quest-giver.

For radial jobs that repeat infinitely, some players report the quest pointer directing them to an unfinished area (a location that never “completes”). This happens rarely, but if you’re stuck in a burglary with no clear target, abandon the job and accept a new one from Delvin or Vex. You lose a small amount of reputation, but it’s better than being permanently stuck.

Newer patches (particularly the Anniversary Edition updates) have fixed most critical bugs, but playing on older versions of Skyrim means you’re more vulnerable to these issues. If you’re on console (PS5, Xbox Series X/S) or playing through Game Pass, ensure your game is fully updated.

Optimal Character Builds For Success

The Thieves Guild questline doesn’t demand a specific build, but certain skills smooth the experience considerably. A dedicated thief should invest in Pickpocket, Lockpicking, and Stealth as primary stats. These three skills unlock the majority of job types without friction.

If you’re playing a warrior or mage who’s only dabbling in thievery, focus on Lockpicking first, it’s the bottleneck skill. Raiding jobs and burglaries both rely on it, and you’ll unlock them more easily with 40+ Lockpicking than with 20. Stealth is secondary: if you’re a heavy-armor warrior, you can often brute-force burglaries by fighting your way through guards.

Spellcasters should prioritize Illusion magic. Invisibility and Muffle spells trivialize stealth jobs. A single casting of Invisibility (cost: ~100 Magicka) lets you waltz through a guarded location completely undetected. Pair this with a Pickpocket bonus (through a stolen Thieves Guild armor piece that fortifies Pickpocket) and you’re unstoppable.

For all builds, enchanted gear matters. Equip a ring or gloves that fortify either Pickpocket or Lockpicking, and you’ll notice the difference immediately. These enchantments stack with skill perks, turning a moderate thief into a master quickly. Similarly, Invisibility potions are cheap to craft (Imp Stool + Scaly Pholiota + Namira’s Rot) and invaluable for burglaries when you’re underprepared.

Maximizing Quest Rewards And Long-Term Benefits

Loot And Skill Progression

The five jobs assigned in “With Friends Like These” reward you with straightforward gold, typically 25–75 gold per job depending on difficulty. That’s not a fortune, but it adds up. More valuably, you’ll loot rooms, safes, and corpses during these jobs, and many Thieves Guild locations contain enchanted items, gems, and jewelry that fence for 100+ gold each. A single burglary might yield 300–500 gold in loot, turning a 50-gold job reward into a 350+ gold haul.

Skill progression is the hidden benefit. Each theft, burglary, and pickpocket attempt trains your Pickpocket or Lockpicking skill. Completing five jobs with emphasis on Lockpicking-heavy burglaries can raise your Lockpicking from 20 to 35+ if you started low. This compounds during the restoration quests, where higher-level jobs train skills faster. By the time you’ve completed all four regional restorations, you’ll have naturally leveled your thief skills by 30+ points without grinding.

The gear you acquire is another factor. The Thieves Guild armor set, light armor with +20% Pickpocket bonus, is earned as you progress. Once you’re wearing it, every subsequent pickpocket job gets easier, and the skill gains accelerate. This creates a positive feedback loop where early investment in one or two jobs pays dividends across the entire questline.

Guild Perks And Exclusive Access

Completion of “With Friends Like These” and the subsequent restoration quests unlocks access to guild-exclusive perks and benefits. First, Delvin and Vex become reliable fences, meaning they’ll buy stolen goods at full value (with your Thieves Guild faction status boosting reputation). This is crucial because fencing stolen items is how you convert loot into gold without raising alarm.

Second, you unlock access to the Guild’s hideout in each region. These hideouts contain workbenches, safe storage, and contacts who offer additional jobs and faction quests. The hideouts themselves are secure storage, anything you store there won’t respawn or be lost. For a completionist hoarder, this is invaluable.

Third, completing the restoration quests earns you the respect of Brynjolf, which eventually opens the path to becoming Guildmaster. As Guildmaster, you gain the ability to assign jobs to other Guild members, control faction politics, and unlock the ultimate Guild quest (retrieving the legendary artifact from Snow Veil Sanctum). These quests reward rare enchanted items and significant gold.

Finally, Guild membership provides a hidden benefit: NPCs affiliated with the Guild, which includes most major crime figures in Skyrim, will treat you with deference once you’re established. This doesn’t grant explicit gameplay bonuses, but it opens dialogue options and quests that non-members can’t access. For players interested in Diverse Skyrim: Uncover the various political and social factions of Tamriel, Guild membership is essential roleplaying.

Reports from experienced players on sites like IGN and Twinfinite confirm that Guild members also gain access to discounted training from Guild-affiliated trainers (particularly in Pickpocket and Lockpicking), saving thousands of gold on skill leveling compared to independent trainers. Also, the Guild’s black market in the Flagon stocks items and spell tomes that legitimate merchants refuse to sell, including paralysis poisons, invisibility potions, and pickpocket-boosting enchanted gear.

For players pursuing a stealth-focused playstyle, the long-term benefits of completing “With Friends Like These” and the restoration quests cannot be overstated. You’re not just earning gold and items, you’re building a character whose skills, equipment, and reputation align perfectly with the identity you’ve chosen.

Conclusion

“With Friends Like These” is far more than a simple introductory quest for the Thieves Guild. It’s the foundation of a questline that spans hours of gameplay and fundamentally changes how you interact with Skyrim’s criminal underworld. From the initial five jobs assigned by Delvin and Vex to the sprawling restoration quests that follow, this questline offers mechanical depth, genuine story beats, and tangible rewards that benefit any character type.

The key to success is understanding what each job type demands, building your character accordingly, and treating the restoration quests as real story beats rather than grinding chores. You’ll acquire thousands of gold in loot, unlock exclusive vendor access, and eventually position yourself to become Thieves Guildmaster, one of Skyrim’s most impactful positions.

Whether you’re a dedicated stealth archer planning your entire playthrough around the Guild or a warrior who stumbled into the Flagon out of curiosity, “With Friends Like These” rewards attention and preparation. Return to this guide whenever a job stumps you, and you’ll find yourself progressing smoothly through one of Skyrim’s most rewarding questlines. The Guild awaits.