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As noted in the Player’s Handbook, surprise is not always assured nor is the check always necessary. Light, excessive noise, and other types of prior warning can cancel the need for the check. Surprise isn’t usually possible when no form of concealment is possible (as in the case of two ships at sea), though darkness, storms, fog, and the like do act as concealment.
In some cases, one side may be able to surprise the other without the other group having the same opportunity. This is particularly true when the player characters are using lanterns or torches and the monsters are not. Seeing the light, the monsters can try to sneak closer and get the jump on the player characters.

Sometimes an encounter, either random or planned by the DM, catches one of the two groups involved totally off guard. This is called surprise and is determined by rolling 1d10 for each side (or only one side if the DM has decided that one of the sides cannot be surprised, for some reason). If the die roll is a 1, 2, or 3, that group or character is surprised (for effects, see the “Effects of Surprise” section). Naturally, surprise does not happen all the time. There are many easy and intelligent ways it can be prevented. The most obvious is if the player characters can see those they are about to encounter well before getting close.

Other Party is:	Modifier
Silenced	-2
Invisible	-2
Distinctive odor (smoke, powerful stench, etc.)	+2
Every 10 members	+1
Camouflaged	-1 to -3
PC Party is:
Fleeing	-2
In poor light	-1
In darkness	-4
Panicked	-2
Anticipating attack*	+2
Suspicious*	+2
Conditions are:
Rainy	-1
Heavy fog	-2
Extremely still	+2

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Encounter Distance

Situation or Terrain	Range in Feet
Both groups surprised	3d6
One group surprised	4d6
No surprise:
Smoke or heavy fog	6d6
Jungle or dense forest	1d10 x 10
Light forest	2d6 x 10
Scrub, brush or bush	2d12 x 10
Grassland, little cover	5d10 x 10
Nighttime or dungeon	Limit of sight

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Effects of Surprise:
Characters and monsters that are surprised all suffer the same penalty. They are caught off guard and thus cannot react quickly.

• The surprising group receives one round of attacks with melee, missile, or magical items. They cannot use these moments of surprise to cast spells.
• The second effect of surprise is that the surprised characters lose all AC bonuses for high Dexterity during that instant of surprise. The surprised characters are dumbfounded by the attack. Instead of ducking and countering, they’re just standing there rather flat-footed (maybe even with dumb expressions on their faces). Since they don’t grasp the situation, they cannot avoid the hazards and dangers very well.
• If both groups manage to surprise each other, the effects of surprise are cancelled.

Surprise can also be used to avoid an encounter. Unsurprised characters can attempt to flee from a surprised group before the other group reacts. Of course, this is not always successful, since escape is greatly dependent upon the movement rates of the different creatures.