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.

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