|Defeat cond.||The pup is captured|
|Travel to 2 lands[N 1]|
|Travel to 5 lands|
|Travel to 10 lands[N 2]|
|Only feral rulers will find this crown!|
|Travel to 2 lands and each pay for at least 10 ship pieces|
|Travel to 5 lands with a full ship and each pay for at least 20 ship pieces|
|Travel to 10 lands with a full ship and each pay for 30 ship pieces|
|Only for feral and logistical rulers!|
Raw Fury description
“ With the new Dire Wolf mount as your aid, protect its pup at all costs. No crown, no monarch. No pup, no monarch! Now build the boat and try to escape as you run to as many islands as possible before the inevitable.—Raw Fury  „
|Mines|| Stone [Bug 1]|
Iron [Bug 1]
|Chests|| Coin chests 3|
|Boat||Has to be fully paid|
The wolf pup follows its mother from the beginning.
The main difference is that the pup cannot be rescued, as the defeat screen is triggered instantly the moment a greedling touches it. So the wolf charge is only useful before this moment.
Co-op – Both Monarchs have to keep their pups. If one Monarch loses their little wolf, the challenge is over.
Note that the Monarch can still lose the challenge if a greedling takes the Crown, however, losing the pup is a lot more likely to happen, given the pup's position that's not fully controllable and the fact that it can be taken even if the Monarch has coins in the pouch.
Unlike the campaign, the number of portals is the same on every island.
Spanning the islands
The Dire Island is for speedrunners. Each coin spent on anything not absolutely necessary, means one coin not invested (or delayed to be invested) on the boat, which probably means the Monarch will not travel to as much islands as he/she could. The major distractors are:
- the Banker
- the stone technology on the very first island.
- the iron technology for the first islands.
- the town center for the first island.
- destroying portals
- towers and pikemen
There is an overall day count, as in the Two Crowns campaign, making waves and Blood Moons harder as the days pass. However, waves tend to be easier during the first two days on each island, giving the Monarch enough time to build stone walls when it becomes necessary. Even on Blood Moons, only greedlings and masked greedlings spawn, without breeder, floater or crown stealer.
Single player – Only feral rulers will find this crown!
- To get the cursed crown in Dire Island in single player mode, the Monarch has to travel to the tenth island, i.e. use the boat nine times (gold crown requirement) and to kill a certain amount of greedlings with the wolf's charge. If the required amount of greed is killed before traveling to the tenth island, the Monarch will receive the cursed crown instead of the gold one when traveling there.
Cooperative – Only for feral and logistical rulers!
- [ ? ]
These are the current speedrun world records held on Dire Island: 
|1st||xSpitez||1h 25m||7 Sep 2020|
|2nd||AmenekoGames||1h 34m||31 Jul 2020|
|3rd||Captain Stanhope||1h 38m||25 Apr 2020|
Currently all records were held on PC on the European setting.
- Once paid for the stone and iron mines, if they are activated for all next islands, the expected behavior is that these mines do not reappear on next islands or, if they do, they should have at least the aspect of activated mines and not accept coins at all. But since the release of Challenge Islands up to the current state of the game, the mines on next islands still have their natural appearance and accept coins. This can confuse inexperienced monarchs, and make them spoil their resources unnecessarily.
- Entering the challenge already counts as the first travel. Therefore, travelling to the second island already grants the bronze crown.
- Once the Monarch has travelled to nine lands, acquiring the gold crown, it is still possible to visit new islands.
- 29 August 2019.
- As shared by the speedrunner One-Dragon and confirmed by the developer Gordon on , on November 2020.
- Details at speedrun.com.