I have seen dynamic difficulty done well exactly once: in an obscure freeware game called Quadnet by Brainchild Design. It is a simple arcade game that focuses on honing a single skill. There are three lives. Mastery at the game means speed in accomplishing the game's objective; it ramps up the difficulty during the first life in response to the player such that after about 5 minutes you've reached your max and you die. It then spends the next two lives very slowly rocking the player back and forth over that difficulty threshold they can't pass.
It works because there is no penalty for skill -- better players are guaranteed to get more points and faster -- and because it is true to the game: the advance in difficulty works to train you at the game's main skill, find your comfort level, and they try to push you past it.
In general, dynamic difficulty is done wrong in two ways: it changes the fundamental game or cheats, distorting the landscape players are trying to conquer, and it does not reward them with points or bragging rights for having triggered the harder mode.
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The danger is doing it naively, and winding up with Rubber Band AI: http://tvtropes.org/pmwiki/pmwiki.php/Main/RubberBandAI
I have seen dynamic difficulty done well exactly once: in an obscure freeware game called Quadnet by Brainchild Design. It is a simple arcade game that focuses on honing a single skill. There are three lives. Mastery at the game means speed in accomplishing the game's objective; it ramps up the difficulty during the first life in response to the player such that after about 5 minutes you've reached your max and you die. It then spends the next two lives very slowly rocking the player back and forth over that difficulty threshold they can't pass.
It works because there is no penalty for skill -- better players are guaranteed to get more points and faster -- and because it is true to the game: the advance in difficulty works to train you at the game's main skill, find your comfort level, and they try to push you past it.
In general, dynamic difficulty is done wrong in two ways: it changes the fundamental game or cheats, distorting the landscape players are trying to conquer, and it does not reward them with points or bragging rights for having triggered the harder mode.