DDS2 has several achievements with opaque unlock conditions. By cross-referencing Steam Community guides (including the "EN Achievements 100%" guide), tracking sites like Steam Hunters and PlayTracker, and GameFAQs, I pieced together the requirements for the hardest-to-unlock achievements. This guide focuses on achievements where the unlock condition is not obvious from the name alone.

Achievements with unclear conditions:

Several achievements on Steam have descriptions that do not clearly state what you need to do:

Achievement Verified Condition Community Guess Rarity
Never let you down Complete a specific quest chain Possibly related to a story choice Very rare
A warm place Unknown -- hideout upgrade related Possibly full upgrade of a specific hideout Very rare
Home sweet home Fully upgrade a hideout Any hideout maxed out Rare
Side hustle Sell 100 baskets Baskets are crafted from palm leaves 0.6%
500 CIGARETTES Sell 500 cigarettes total Grind from vendors 0.7%
No buddy I am not lost Kill 50 thugs Thugs are gang members found in various territories Moderate
Do You Know the Muffin Man? Bake 420 cookies Cookie recipe required Moderate
Nap with the fishes Drown in water due to exhaustion Swim until stamina depletes Moderate
Environmentalist Sell 100 glass bottles Collect bottles everywhere ~12.6%
"Side hustle" has a 0.6% unlock rate on Steam. This makes it one of the rarest base-game achievements. It requires crafting and selling 100 baskets, which means gathering palm leaves from beach areas, crafting baskets at a workbench, and selling them. This is a long grind that is easy to miss if you do not start collecting palm leaves early.

DLC achievements:

The Casino DLC adds achievements with more clearly defined conditions. Based on the Steam Community 100% guide:

Achievement DLC Condition
Casino-related Casino DLC Complete casino missions
Casino boss elimination Casino DLC Eliminate boss with bomb, pay B4,000,000
Gambling achievements Casino DLC Win at roulette, slots, and other casino games

The casino DLC was released around June 2025 and adds a full new zone with gambling mechanics, new NPCs, and boss encounters. The 100% achievement guide on Steam covers these in detail including the bomb strategy for the casino boss.

Practical example: How to unlock "500 CIGARETTES" efficiently

This is one of the grindiest achievements in the game. Here is the most efficient approach:

  1. Check every general store and vendor for cigarette stock. Key locations include the stores in Callejon, Jungle, and Archipelago.
  2. Buy all available cigarettes whenever you visit a vendor. Do not skip this even if you have other purchases planned.
  3. Store cigarettes in a dedicated hideout that you use as a supply hub. Do not mix them with other products.
  4. Assign a dealer to sell cigarettes in a high-traffic territory. Cigarettes have fast turnover because the demand exists in multiple islands.
  5. Track your progress through the Steam overlay. The achievement triggers at 500 units sold, not purchased.

At approximately 10-20 cigarettes available per store visit, expect 25-50 vendor trips minimum. This achievement takes most players 30-40 hours of gameplay.

100% completion strategy:

Based on the Steam community "EN Achievements 100%" guide and cross-referencing with the Casino DLC guide:

  1. Story first -- Progress through the main questline to unlock base achievements. This includes "You're hired!" (hire first employee) and story-related progression.
  2. Street Cred grind -- "I Am The One Who Knocks" (level 4) and "The Kingpin" (max level). Beat gang members and complete influencer missions.
  3. Misc collectibles -- Start collecting glass bottles, cigarettes, and palm leaves from hour one. Do not wait until you need them.
  4. Combat achievements -- "No buddy I am not lost" (50 thugs). Gang member spawn locations are consistent across restarts.
  5. Casino DLC -- Complete after the base game. The DLC has its own story missions and boss fights.

Difficulty tier list:

Tier Achievement Estimated Time
Easy You're hired! (Hire first employee) 1-2 hours
Easy I Am The One Who Knocks (Street Cred 4) 10-15 hours
Medium Environmentalist (100 bottles) 15-20 hours
Medium Do You Know the Muffin Man? (420 cookies) 15-25 hours
Medium Nap with the fishes 10-15 hours
Hard 500 CIGARETTES 30-40 hours
Hard No buddy I am not lost (50 thugs) 20-30 hours
Very Hard Side hustle (100 baskets) 40-60 hours
Extreme The Kingpin (max Street Cred) 40-50 hours
Extreme 100% (all achievements + DLC) 80-100 hours
For "Nap with the fishes," simply swim out from any beach until your stamina bar drains completely. You do not need to find deep water specifically -- any body of water works. Make sure you do not have any active quest items or large amounts of cash before attempting this, as drowning resets your position.

Related Guides:

Community Verification & Resources

Data values may shift with patches. Cross-check against community resources before building your strategy.

100% Achievement Guide EN guide to all achievements with casino boss strategy Casino DLC Achievement Guide Casino-specific achievement guide with DLC content Steam Hunters DDS2 Detailed rarity data for all 39 achievements 100% Completion Video Video walkthrough of mastering DDS2 to 100%