The Settlers Online Wiki
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Description[]

Difficulty is a measure of how difficult an adventure is. Every adventure is given a difficulty rating in skulls.  The more skulls are shown, the harder the adventure is.

The difficulty rating is shown when you select an adventure from your Star Menu, before you click the Start button.

Obviously, all adventures become easier as you progress in the game, and get better troops, so the difficulty rating should be treated as just a guide.

Ratings[]

Ratings range from 1 skull up to 9 skulls.

Easiest: can be completed with just recruits.
Very Easy: Simple attacks with basic troops
Easy: Can be completed with a small army of basic troops (up to Militia)
Easy-ish: Losses are heavier, but can usually be completed alone.
Medium: Probably requires 2 players doing blocks, to share the losses.
Hard-ish: Heavy losses, requiring Veteran General and blocks.
Hard: Usually for 2-3 players with Vets, but has heavy losses
Tough!: Probably requiring 3 players with heavy losses
Very Tough!: Expect to struggle
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