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:

AchievementVerified ConditionCommunity GuessRarity
Never let you downComplete a specific quest chainPossibly related to a story choiceVery rare
A warm placeUnknown -- hideout upgrade relatedPossibly full upgrade of a specific hideoutVery rare
Home sweet homeFully upgrade a hideoutAny hideout maxed outRare
Side hustleSell 100 basketsBaskets are crafted from palm leaves0.6%
500 CIGARETTESSell 500 cigarettes totalGrind from vendors0.7%
No buddy I am not lostKill 50 thugsThugs are gang members found in various territoriesModerate
Do You Know the Muffin Man?Bake 420 cookiesCookie recipe requiredModerate
Nap with the fishesDrown in water due to exhaustionSwim until stamina depletesModerate
EnvironmentalistSell 100 glass bottlesCollect 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:

AchievementDLCCondition
Casino-relatedCasino DLCComplete casino missions
Casino boss eliminationCasino DLCEliminate boss with bomb, pay B4,000,000
Gambling achievementsCasino DLCWin 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:

TierAchievementEstimated Time
EasyYou're hired! (Hire first employee)1-2 hours
EasyI Am The One Who Knocks (Street Cred 4)10-15 hours
MediumEnvironmentalist (100 bottles)15-20 hours
MediumDo You Know the Muffin Man? (420 cookies)15-25 hours
MediumNap with the fishes10-15 hours
Hard500 CIGARETTES30-40 hours
HardNo buddy I am not lost (50 thugs)20-30 hours
Very HardSide hustle (100 baskets)40-60 hours
ExtremeThe Kingpin (max Street Cred)40-50 hours
Extreme100% (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.

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