The seventeen key items of Free Enterprise are:

Shuffling the locations of these items is the core gameplay element of the Free Enterprise randomizer, sending players to explore different paths each time the game is played. The various K flags control where key items can be found.

Each key item appears at most once. Every key item is guaranteed to appear, except in cases where there are not enough potential positions to fit them all, which will cause either Spoon or Pink Tail to be omitted.

Even if the Pass is included in the key item distribution using Pkey, the Pass itself does not count as a key item. (See Pass settings.)

Kmain is the core key item randomization flag, and is required when playing with randomized key items. When enabled, this flag allows key items to potentially by won by:

• Receiving the starting item during the opening Baron Castle cutscene
• Completing the Antlion's Nest
• Defending Fabul
• Entering the mirror room atop Mt. Ordeals
• Defeating the Baron Inn bosses
• Liberating Baron Castle
• Speaking to Edward in Toroia Castle*
• Completing Cave Magnes
• Completing the Tower of Zot
• Defeating the boss of lower Bab-il
• Destroying the Super Cannon (reward is delivered when leaving the tower afterward)
• Defeating the Dwarf Castle bosses
• Completing the Sealed Cave
• In the “Rat Tail chest” in the Town of Summons
• Speaking to Yang's wife after finding Yang in the Sylph Cave
• Returning the Pan to Yang's wife after using it to wake him up
• Trading the Rat Tail in the Adamant Grotto

When playing with the “No Free Key Item” challenge, the “speak to Edward in Toroia” reward is replaced with “go to Rydia's mother in Mist after finding and defeating D. Mist”. (See No Free Lunch challenges.)

Adding the Ksummon flag allows key items to also potentially be won:

• From the Sylphs when waking Yang in the Sylph Cave
• By defeating the queen of the Town of Monsters
• By defeating the king of the Town of Monsters
• By defeating the ghost on the throne under Baron Castle
• By completing Cave Bahamut

(These locations correspond to the vanilla locations where Rydia learns Sylph, Asura, Leviatan, Odin, and Bahamut respectively.)

Setting Kmoon allows key items to potentially appear as rewards for defeating the sub-bosses in the Lunar Subterrane. (These locations correspond to the vanilla locations of the Murasame, Crystal Sword, White Spear, two Ribbons, and Masamune.)

Setting Ktrap allows key items to potentially appear as rewards from trapped treasure chests (ie. those containing monsters). For a list of trapped chests and details about their randomization, see Treasure randomization.

The randomizer applies some fuzzy logic in order to help spread the key items more evenly around the world. The algorithm is roughly as follows:

• Start with the pool of main quest key item positions.
• If Ksummon and/or Kmoon are set,
  • Randomly select half the slots made available by Ksummon and/or Kmoon, rounded up, and add them to the pool.
  • Generate a random number N from 0…1.
  • Determine the greatest integer K, where N < 1/(2^K).
  • Add K more of the available summon/moon slots to the pool.
  • Reserve the remaining unselected summon/moon slots.
• If Ktrap is set,
  • For each dungeon containing trapped chests,
    • Generate a random number N from 0…1.
    • Determine the greatest integer K, where N < 1/(2^K).
    • Select (K + 2) random trapped chests in the dungeon and add them to the pool (or all of them, if there are fewer than K + 2).
    • Reserve the remaining unused trapped chests.
• Randomly assign key items among the slots in the pool.
• The remaining unassigned slots in the pool, as well as the reserved slots from the summon/moon/trap steps, will receive non-key-item rewards.

Free Enterprise uses a random fill algorithm, verifying that each randomization is valid, and retrying if that test fails.

From observation, with a straightforward randomization approach, about 75% of seeds end up being “Hook seeds”, ie. seeds where the Magma Key is not readily available and the Hook is required to access the underworld, a much more difficult route with two challenging boss battles.

To ease the difficulty for newer players, when generating a seed without any of the extended key item position flags (summon, moon, and traps), the randomizer has a 50/50 chance of forcing a Magma Key underworld route to be available.

To help ensure a reasonable progression through the game, the randomizer guarantees there will be a path to the underworld that does not require going to the moon first. This check can be disabled using Kunsafe.

Potential key item locations that are not assigned a key item instead deliver an alternate reward, dependent on treasure flag settings. (Also see Treasure randomization.)

Under Tvanilla or Tshuffle, a pool is created containing the vanilla rewards from all potential extended key item locations, (eg. if Kmoon is set, add Murasame, Crystal Sword, White Spear, two Ribbons, and Masamune), and randomly assign the non-key-item rewards from this pool.

Under Tstandard or Twild:

• Unused trapped chests receive a random item from tier 5-7.
• All other unused potential key item locations receive a random item from tier 6-7.

Under Tpro and Twildish, non-key-item rewards are assigned based on their corresponding Treasure probability curves.

If not playing with randomized key items, the key items can be found in their vanilla locations, with some exceptions:

• Defending Fabul awards the Black Sword.
• Liberating Baron Castle has no reward.
  • If combining ​Kvanilla​ with ​Pkey,​ liberating Baron Castle awards the Pass.
• The Legend Sword is awarded atop Mt. Ordeals; it does not come with Paladin Cecil.
• The Hook is earned by the destroying the Super Cannon, and is awarded during the cutscene when trying to leave the tower afterward.
• If playing with No Free Key Item, the TwinHarp is awarded by Rydia'​s mom.
• The Pink Tail is not available. (PinkPuffs directly drop Adamant Armors instead of Pink Tails in Free Enterprise.)
• The Crystal, as in vanilla, is awarded in the cutscene directly before fighting Zeromus.
  • The Crystal is not awarded here if playing with objectives that award the Crystal.