diff --git a/soh/soh/Enhancements/debugger/debugSaveEditor.h b/soh/soh/Enhancements/debugger/debugSaveEditor.h
index e4b4ad76e..f8e692ee4 100644
--- a/soh/soh/Enhancements/debugger/debugSaveEditor.h
+++ b/soh/soh/Enhancements/debugger/debugSaveEditor.h
@@ -496,5 +496,7 @@ const std::vector<FlagTable> flagTables = {
         { RAND_INF_ADULT_TRADES_DMT_TRADE_BROKEN_SWORD, "ADULT_TRADES_DMT_TRADE_BROKEN_SWORD" },
         { RAND_INF_ADULT_TRADES_LH_TRADE_FROG, "ADULT_TRADES_LH_TRADE_FROG" },
         { RAND_INF_ADULT_TRADES_DMT_TRADE_EYEDROPS, "ADULT_TRADES_DMT_TRADE_EYEDROPS" },
+
+        { RAND_INF_KAK_100_GOLD_SKULLTULA_REWARD, "KAK_100_GOLD_SKULLTULA_REWARD" },
     } },
 };
\ No newline at end of file
diff --git a/soh/soh/Enhancements/randomizer/3drando/fill.cpp b/soh/soh/Enhancements/randomizer/3drando/fill.cpp
index 0e8ab67e1..84fce11a2 100644
--- a/soh/soh/Enhancements/randomizer/3drando/fill.cpp
+++ b/soh/soh/Enhancements/randomizer/3drando/fill.cpp
@@ -148,7 +148,10 @@ static int GetMaxGSCount() {
   //Get the max amount of GS which could be useful from token reward locations
   int maxUseful = 0;
   //If the highest advancement item is a token, we know it is useless since it won't lead to an otherwise useful item
-  if (Location(KAK_50_GOLD_SKULLTULA_REWARD)->GetPlacedItem().IsAdvancement() && Location(KAK_50_GOLD_SKULLTULA_REWARD)->GetPlacedItem().GetItemType() != ITEMTYPE_TOKEN) {
+  if (Location(KAK_100_GOLD_SKULLTULA_REWARD)->GetPlacedItem().IsAdvancement() && Location(KAK_100_GOLD_SKULLTULA_REWARD)->GetPlacedItem().GetItemType() != ITEMTYPE_TOKEN) {
+    maxUseful = 100;
+  }
+  else if (Location(KAK_50_GOLD_SKULLTULA_REWARD)->GetPlacedItem().IsAdvancement() && Location(KAK_50_GOLD_SKULLTULA_REWARD)->GetPlacedItem().GetItemType() != ITEMTYPE_TOKEN) {
     maxUseful = 50;
   }
   else if (Location(KAK_40_GOLD_SKULLTULA_REWARD)->GetPlacedItem().IsAdvancement() && Location(KAK_40_GOLD_SKULLTULA_REWARD)->GetPlacedItem().GetItemType() != ITEMTYPE_TOKEN) {
diff --git a/soh/soh/Enhancements/randomizer/3drando/hint_list.cpp b/soh/soh/Enhancements/randomizer/3drando/hint_list.cpp
index f52d1091c..ba47ad92d 100644
--- a/soh/soh/Enhancements/randomizer/3drando/hint_list.cpp
+++ b/soh/soh/Enhancements/randomizer/3drando/hint_list.cpp
@@ -74,6 +74,25 @@ void HintTable_Init() {
         Text{ "#Malon's obstacle course# leads to", /*french*/ "la #course à obstacle de Malon# amène à",
               /*spanish*/ "la #carrera de obstáculos de Malon# brinda" });
 
+    hintTable[KAK_100_GOLD_SKULLTULA_REWARD] = HintText::Always(
+        {
+            // obscure text
+            Text{ "#100 bug badges# rewards",
+                  /*french*/ "#100 écussons# donnent",
+                  /*spanish*/ "#100 medallas de insectos# otorgan" },
+            Text{ "#100 spider souls# yields",
+                  /*french*/ "#100 âmes d'arachnide# donnent",
+                  /*spanish*/ "#100 almas de araña# otorgan" },
+            Text{ "#100 auriferous arachnids# lead to",
+                  /*french*/ "#100 arachnides aurifères# donnent",
+                  /*spanish*/ "#100 arácnidos auríferos# otorgan" },
+        },
+        {},
+        // clear text
+        Text{ "slaying #100 Gold Skulltulas# reveals",
+              /*french*/ "détruire #100 Skulltulas d'or# donne",
+              /*spanish*/ "exterminar #100 skulltulas doradas# revela" });
+
     /*--------------------------
     |    SOMETIMES HINT TEXT   |
     ---------------------------*/
@@ -2699,6 +2718,13 @@ void HintTable_Init() {
               /*spanish*/ "Y el héroe recibirá la llave del #señor del mal# cuando haya completado la #Trifuerza#." },
     });
 
+    hintTable[GANON_BK_SKULLTULA_HINT] = HintText::GanonsBossKey({
+        // obscure text
+        Text { "And the %revil one%w's key will be&provided by the cursed rich man&once %r100 Gold Skulltula Tokens%w&are retrieved.",
+              /*french*/ "Aussi, la %rclé du Malin%w sera&donnée par l'homme maudit une&fois que %r100 Symboles de&Skulltula d'or%w auront été trouvés.",
+              /*spanish*/ "Y el rico maldito entregará la llave&del #señor de mal# tras obtener&100 símbolos de skulltula dorada#."},
+    });
+
     /*--------------------------
     |      LACS HINT TEXT      |
     ---------------------------*/
diff --git a/soh/soh/Enhancements/randomizer/3drando/hints.cpp b/soh/soh/Enhancements/randomizer/3drando/hints.cpp
index 6b613246b..09c6a6528 100644
--- a/soh/soh/Enhancements/randomizer/3drando/hints.cpp
+++ b/soh/soh/Enhancements/randomizer/3drando/hints.cpp
@@ -653,6 +653,9 @@ static Text BuildGanonBossKeyText() {
   } else if (GanonsBossKey.Is(GANONSBOSSKEY_ANYWHERE)) {
     ganonBossKeyText = Hint(GANON_BK_ANYWHERE_HINT).GetText();
 
+  } else if (GanonsBossKey.Is(GANONSBOSSKEY_FINAL_GS_REWARD)) {
+    ganonBossKeyText = Hint(GANON_BK_SKULLTULA_HINT).GetText();
+
   } else if (GanonsBossKey.Is(GANONSBOSSKEY_LACS_VANILLA)) {
     ganonBossKeyText = Hint(LACS_VANILLA_HINT).GetText();
 
diff --git a/soh/soh/Enhancements/randomizer/3drando/item_location.cpp b/soh/soh/Enhancements/randomizer/3drando/item_location.cpp
index d88117cec..d91511f98 100644
--- a/soh/soh/Enhancements/randomizer/3drando/item_location.cpp
+++ b/soh/soh/Enhancements/randomizer/3drando/item_location.cpp
@@ -116,6 +116,7 @@ void LocationTable_Init() {
     locationTable[KAK_30_GOLD_SKULLTULA_REWARD]          = ItemLocation::Base       (RC_KAK_30_GOLD_SKULLTULA_REWARD,               0x50, 0x46, "Kak 30 Gold Skulltula Reward",         KAK_30_GOLD_SKULLTULA_REWARD,          PROGRESSIVE_WALLET,        {Category::cKakarikoVillage, Category::cKakariko, Category::cSkulltulaHouse},                                         SpoilerCollectionCheck::EventChkInf(0xDC),               SpoilerCollectionCheckGroup::GROUP_KAKARIKO);
     locationTable[KAK_40_GOLD_SKULLTULA_REWARD]          = ItemLocation::Base       (RC_KAK_40_GOLD_SKULLTULA_REWARD,               0x50, 0x03, "Kak 40 Gold Skulltula Reward",         KAK_40_GOLD_SKULLTULA_REWARD,          BOMBCHU_10,                {Category::cKakarikoVillage, Category::cKakariko, Category::cSkulltulaHouse},                                         SpoilerCollectionCheck::EventChkInf(0xDD),               SpoilerCollectionCheckGroup::GROUP_KAKARIKO);
     locationTable[KAK_50_GOLD_SKULLTULA_REWARD]          = ItemLocation::Base       (RC_KAK_50_GOLD_SKULLTULA_REWARD,               0x50, 0x3E, "Kak 50 Gold Skulltula Reward",         KAK_50_GOLD_SKULLTULA_REWARD,          PIECE_OF_HEART,            {Category::cKakarikoVillage, Category::cKakariko, Category::cSkulltulaHouse},                                         SpoilerCollectionCheck::EventChkInf(0xDE),               SpoilerCollectionCheckGroup::GROUP_KAKARIKO);
+    locationTable[KAK_100_GOLD_SKULLTULA_REWARD]         = ItemLocation::Base       (RC_KAK_100_GOLD_SKULLTULA_REWARD,              0x50, 0x3E, "Kak 100 Gold Skulltula Reward",        KAK_100_GOLD_SKULLTULA_REWARD,         HUGE_RUPEE,                {Category::cKakarikoVillage, Category::cKakariko, Category::cSkulltulaHouse},                                         SpoilerCollectionCheck::EventChkInf(0xDF),               SpoilerCollectionCheckGroup::GROUP_KAKARIKO);
     locationTable[KAK_MAN_ON_ROOF]                       = ItemLocation::Base       (RC_KAK_MAN_ON_ROOF,                            0x52, 0x3E, "Kak Man on Roof",                      KAK_MAN_ON_ROOF,                       PIECE_OF_HEART,            {Category::cKakarikoVillage, Category::cKakariko,},                                                                   SpoilerCollectionCheck::ItemGetInf(29),                  SpoilerCollectionCheckGroup::GROUP_KAKARIKO);
     locationTable[KAK_SHOOTING_GALLERY_REWARD]           = ItemLocation::Base       (RC_KAK_SHOOTING_GALLERY_REWARD,                0x42, 0x30, "Kak Shooting Gallery Reward",          KAK_SHOOTING_GALLERY_REWARD,           PROGRESSIVE_BOW,           {Category::cKakarikoVillage, Category::cKakariko, Category::cMinigame},                                               SpoilerCollectionCheck::Chest(0x42, 0x1F),               SpoilerCollectionCheckGroup::GROUP_KAKARIKO);
     locationTable[KAK_TRADE_ODD_MUSHROOM]                = ItemLocation::Base       (RC_KAK_TRADE_ODD_MUSHROOM,                     0x4E, 0x20, "Kak Trade Odd Mushroom",               KAK_TRADE_ODD_MUSHROOM,                ODD_POTION,                {Category::cKakarikoVillage, Category::cKakariko, Category::cAdultTrade},                                             SpoilerCollectionCheck::ItemGetInf(56),                  SpoilerCollectionCheckGroup::GROUP_KAKARIKO);
@@ -1276,6 +1277,7 @@ std::vector<uint32_t> overworldLocations = {
   KAK_30_GOLD_SKULLTULA_REWARD,
   KAK_40_GOLD_SKULLTULA_REWARD,
   KAK_50_GOLD_SKULLTULA_REWARD,
+  KAK_100_GOLD_SKULLTULA_REWARD,
   KAK_MAN_ON_ROOF,
   KAK_SHOOTING_GALLERY_REWARD,
   KAK_TRADE_ODD_MUSHROOM,
diff --git a/soh/soh/Enhancements/randomizer/3drando/item_pool.cpp b/soh/soh/Enhancements/randomizer/3drando/item_pool.cpp
index 6cca76be9..b4f4a7c52 100644
--- a/soh/soh/Enhancements/randomizer/3drando/item_pool.cpp
+++ b/soh/soh/Enhancements/randomizer/3drando/item_pool.cpp
@@ -798,6 +798,15 @@ void GenerateItemPool() {
     AddItemToMainPool(GOLD_SKULLTULA_TOKEN, 100);
   }
 
+  if (Shuffle100GSReward) {
+    if (Tokensanity.IsNot(TOKENSANITY_OFF) && ItemPoolValue.Is(ITEMPOOL_PLENTIFUL)) {
+      AddItemToPool(PendingJunkPool, GOLD_SKULLTULA_TOKEN, 10);
+    }
+    AddItemToMainPool(HUGE_RUPEE);
+  } else {
+    PlaceItemInLocation(KAK_100_GOLD_SKULLTULA_REWARD, HUGE_RUPEE, false, true);
+  }
+
   if (BombchusInLogic) {
     AddItemToMainPool(PROGRESSIVE_BOMBCHUS, 5);
   } else {
@@ -1119,7 +1128,9 @@ void GenerateItemPool() {
     AddItemToMainPool(SHADOW_TEMPLE_BOSS_KEY);
   }
 
-  if (GanonsBossKey.Value<uint8_t>() >= GANONSBOSSKEY_LACS_VANILLA) {
+  if (GanonsBossKey.Is(GANONSBOSSKEY_FINAL_GS_REWARD)) {
+    PlaceItemInLocation(KAK_100_GOLD_SKULLTULA_REWARD, GANONS_CASTLE_BOSS_KEY);
+  } else if (GanonsBossKey.Value<uint8_t>() >= GANONSBOSSKEY_LACS_VANILLA) {
     PlaceItemInLocation(TOT_LIGHT_ARROWS_CUTSCENE, GANONS_CASTLE_BOSS_KEY);
   } else if (GanonsBossKey.Is(GANONSBOSSKEY_VANILLA)) {
     PlaceItemInLocation(GANONS_TOWER_BOSS_KEY_CHEST, GANONS_CASTLE_BOSS_KEY);
diff --git a/soh/soh/Enhancements/randomizer/3drando/keys.hpp b/soh/soh/Enhancements/randomizer/3drando/keys.hpp
index 0016ff205..3163d37dd 100644
--- a/soh/soh/Enhancements/randomizer/3drando/keys.hpp
+++ b/soh/soh/Enhancements/randomizer/3drando/keys.hpp
@@ -392,6 +392,7 @@ typedef enum {
   KAK_30_GOLD_SKULLTULA_REWARD,
   KAK_40_GOLD_SKULLTULA_REWARD,
   KAK_50_GOLD_SKULLTULA_REWARD,
+  KAK_100_GOLD_SKULLTULA_REWARD,
   KAK_IMPAS_HOUSE_COW,
   KAK_GS_TREE,
   KAK_GS_GUARDS_HOUSE,
@@ -1762,6 +1763,7 @@ typedef enum {
   GANON_BK_ANY_DUNGEON_HINT,
   GANON_BK_ANYWHERE_HINT,
   GANON_BK_TRIFORCE_HINT,
+  GANON_BK_SKULLTULA_HINT,
 
   LACS_VANILLA_HINT,
   LACS_MEDALLIONS_HINT,
diff --git a/soh/soh/Enhancements/randomizer/3drando/location_access/locacc_kakariko.cpp b/soh/soh/Enhancements/randomizer/3drando/location_access/locacc_kakariko.cpp
index fbd4adff9..d75b06f84 100644
--- a/soh/soh/Enhancements/randomizer/3drando/location_access/locacc_kakariko.cpp
+++ b/soh/soh/Enhancements/randomizer/3drando/location_access/locacc_kakariko.cpp
@@ -97,6 +97,7 @@ void AreaTable_Init_Kakariko() {
                   LocationAccess(KAK_30_GOLD_SKULLTULA_REWARD, {[]{return GoldSkulltulaTokens >= 30;}}),
                   LocationAccess(KAK_40_GOLD_SKULLTULA_REWARD, {[]{return GoldSkulltulaTokens >= 40;}}),
                   LocationAccess(KAK_50_GOLD_SKULLTULA_REWARD, {[]{return GoldSkulltulaTokens >= 50;}}),
+                  LocationAccess(KAK_100_GOLD_SKULLTULA_REWARD, {[]{return GoldSkulltulaTokens >= 100;}})
                 }, {
                   //Exits
                   Entrance(KAKARIKO_VILLAGE, {[]{return true;}}),
diff --git a/soh/soh/Enhancements/randomizer/3drando/setting_descriptions.cpp b/soh/soh/Enhancements/randomizer/3drando/setting_descriptions.cpp
index 8c404f354..1a0544ee1 100644
--- a/soh/soh/Enhancements/randomizer/3drando/setting_descriptions.cpp
+++ b/soh/soh/Enhancements/randomizer/3drando/setting_descriptions.cpp
@@ -368,7 +368,7 @@ string_view tokensOverworld           = "This only shuffles the GS locations tha
                                         "outside of dungeons.";                            //
 string_view tokensAllTokens           = "Effectively adds 100 new locations for items to\n"//
                                         "appear.";                                         //
-                                                                                           //
+
 /*------------------------------                                                           //
 |        SCRUB SHUFFLE         |                                                           //
 ------------------------------*/                                                           //
@@ -471,6 +471,15 @@ string_view chestMinigameDesc         = "The 5 key chests in the Treasure Chest
                                         "\n"                                               //
                                         "If you choose the \"pack\" option, you will get\n"//
                                         "all the keys at once, in a single item.";         //
+                                                                                           //
+/*------------------------------                                                           //
+|    SHUFFLE 100 GS REWARD     |                                                           //
+------------------------------*/                                                           //
+string_view shuffle100GsDesc          = "The cursed rich man in the House of Skulltula\n"  //
+                                        "will give you a random item for collecting all\n" //
+                                        "100 Gold Skulltula Tokens, then he will give you\n"
+                                        "Huge Rupees.";                                    //
+                                                                                           //
 /*------------------------------                                                           //
 |      MAPS AND COMPASSES      |                                                           //
 ------------------------------*/                                                           //
@@ -571,6 +580,9 @@ string_view ganonKeyAnywhere          = "Ganon's Castle Boss Key can appear anyw
 string_view ganonKeyLACS              = "These settings put the boss key on the Light Arrow"
                                         "Cutscene location, from Zelda in Temple of Time as"
                                         "adult, with differing requirements.";             //
+string_view ganonKey100GS             = "Ganon's Castle Boss Key is given to you by the\n" //
+                                        "cursed rich man in the House of Skulltula after\n"//
+                                        "you collect all 100 Gold Skulltula Tokens.";      //
 /*------------------------------                                                           //
 |        LACS CONDITIONS       |                                                           //
 ------------------------------*/                                                           //
diff --git a/soh/soh/Enhancements/randomizer/3drando/setting_descriptions.hpp b/soh/soh/Enhancements/randomizer/3drando/setting_descriptions.hpp
index 096ebf658..b99087944 100644
--- a/soh/soh/Enhancements/randomizer/3drando/setting_descriptions.hpp
+++ b/soh/soh/Enhancements/randomizer/3drando/setting_descriptions.hpp
@@ -148,6 +148,8 @@ extern string_view adultTradeDesc;
 
 extern string_view chestMinigameDesc;
 
+extern string_view shuffle100GsDesc;
+
 extern string_view mapCompassStartWith;
 extern string_view mapCompassVanilla;
 extern string_view mapCompassOwnDungeon;
@@ -183,6 +185,7 @@ extern string_view ganonKeyAnyDungeon;
 extern string_view ganonKeyOverworld;
 extern string_view ganonKeyAnywhere;
 extern string_view ganonKeyLACS;
+extern string_view ganonKey100GS;
 
 extern string_view lacsMedallionCountDesc;
 extern string_view lacsStoneCountDesc;
diff --git a/soh/soh/Enhancements/randomizer/3drando/settings.cpp b/soh/soh/Enhancements/randomizer/3drando/settings.cpp
index 1a4e10a65..b8a05c345 100644
--- a/soh/soh/Enhancements/randomizer/3drando/settings.cpp
+++ b/soh/soh/Enhancements/randomizer/3drando/settings.cpp
@@ -190,6 +190,7 @@ namespace Settings {
   Option ShuffleFrogSongRupees  = Option::Bool("Shuffle Frog Song Rupees",{"Off", "On"},                                                    {frogSongRupeesDesc});
   Option ShuffleAdultTradeQuest = Option::Bool("Shuffle Adult Trade",    {"Off", "On"},                                                     {adultTradeDesc});
   Option ShuffleChestMinigame   = Option::U8  ("Shuffle Chest Minigame", {"Off", "On (Separate)", "On (Pack)"},                             {chestMinigameDesc});
+  Option Shuffle100GSReward     = Option::Bool("Shuffle 100 GS Reward",  {"No", "Yes"},                                                     {shuffle100GsDesc},                                                                                                    OptionCategory::Toggle);
   std::vector<Option *> shuffleOptions = {
     &RandomizeShuffle,
     &ShuffleRewards,
@@ -208,6 +209,7 @@ namespace Settings {
     &ShuffleFrogSongRupees,
     &ShuffleAdultTradeQuest,
     &ShuffleChestMinigame,
+    &Shuffle100GSReward,
   };
 
   //Shuffle Dungeon Items
@@ -220,8 +222,8 @@ namespace Settings {
                                                                          {gerudoKeysVanilla, gerudoKeysAnyDungeon, gerudoKeysOverworld, gerudoKeysAnywhere});
   Option BossKeysanity       = Option::U8  ("Boss Keys",                 {"Start With", "Vanilla", "Own Dungeon", "Any Dungeon", "Overworld", "Anywhere"},
                                                                          {bossKeyStartWith, bossKeyVanilla, bossKeyOwnDungeon, bossKeyAnyDungeon, bossKeyOverworld, bossKeyAnywhere},                                                                              OptionCategory::Setting,    BOSSKEYSANITY_OWN_DUNGEON);
-  Option GanonsBossKey       = Option::U8  ("Ganon's Boss Key",          {"Vanilla", "Own dungeon", "Start with", "Any Dungeon", "Overworld", "Anywhere", "LACS-Vanilla", "LACS-Medallions", "LACS-Stones", "LACS-Rewards", "LACS-Dungeons", "LACS-Tokens"},
-                                                                         {ganonKeyVanilla, ganonKeyOwnDungeon, ganonKeyStartWith, ganonKeyAnyDungeon, ganonKeyOverworld, ganonKeyAnywhere, ganonKeyLACS},                                                          OptionCategory::Setting,    GANONSBOSSKEY_VANILLA);
+  Option GanonsBossKey       = Option::U8  ("Ganon's Boss Key",          {"Vanilla", "Own dungeon", "Start with", "Any Dungeon", "Overworld", "Anywhere", "LACS-Vanilla", "LACS-Medallions", "LACS-Stones", "LACS-Rewards", "LACS-Dungeons", "LACS-Tokens", "100 GS Reward"},
+                                                                         {ganonKeyVanilla, ganonKeyOwnDungeon, ganonKeyStartWith, ganonKeyAnyDungeon, ganonKeyOverworld, ganonKeyAnywhere, ganonKeyLACS, ganonKey100GS},                                           OptionCategory::Setting,    GANONSBOSSKEY_VANILLA);
   uint8_t LACSCondition           = 0;
   Option LACSMedallionCount  = Option::U8  ("Medallion Count",         {NumOpts(0, 6)},                                                        {lacsMedallionCountDesc},                                                                                         OptionCategory::Setting,    1,                          true);
   Option LACSStoneCount      = Option::U8  ("Stone Count",             {NumOpts(0, 3)},                                                        {lacsStoneCountDesc},                                                                                             OptionCategory::Setting,    1,                          true);
@@ -1327,6 +1329,7 @@ namespace Settings {
     ctx.shuffleFrogSongRupees= (ShuffleFrogSongRupees) ? 1 : 0;
     ctx.shuffleAdultTradeQuest = (ShuffleAdultTradeQuest) ? 1 : 0;
     ctx.shuffleChestMinigame = ShuffleChestMinigame.Value<uint8_t>();
+    ctx.shuffle100GsReward   = (Shuffle100GSReward) ? 1 : 0;
 
     ctx.mapsAndCompasses     = MapsAndCompasses.Value<uint8_t>();
     ctx.keysanity            = Keysanity.Value<uint8_t>();
@@ -1823,6 +1826,13 @@ namespace Settings {
       IncludeAndHide(ChestMinigameLocations);
     }
 
+    //Force include 100 GS reward if it isn't shuffled
+    if (Shuffle100GSReward) {
+      Unhide({KAK_100_GOLD_SKULLTULA_REWARD});
+    } else {
+      IncludeAndHide({KAK_100_GOLD_SKULLTULA_REWARD});
+    }
+
     //Force include Map and Compass Chests when Vanilla
     std::vector<uint32_t> mapChests = GetLocations(everyPossibleLocation, Category::cVanillaMap);
     std::vector<uint32_t> compassChests = GetLocations(everyPossibleLocation, Category::cVanillaCompass);
@@ -2069,6 +2079,17 @@ namespace Settings {
       }
     }
 
+    //Only go through options if all settings are not randomized
+    if (!RandomizeShuffle) {
+      // Ganon's Boss Key on 100 GS reward must also have the reward shuffled
+      if (GanonsBossKey.Is(GANONSBOSSKEY_FINAL_GS_REWARD)) {
+        Shuffle100GSReward.SetSelectedIndex(ON);
+        Shuffle100GSReward.Lock();
+      } else {
+        Shuffle100GSReward.Unlock();
+      }
+    }
+
     //Force Link's Pocket Item to be a dungeon reward if Shuffle Rewards is end of dungeons
     if (ShuffleRewards.Is(REWARDSHUFFLE_END_OF_DUNGEON)) {
       LinksPocketItem.Lock();
@@ -2411,6 +2432,7 @@ namespace Settings {
     &ShuffleMerchants,
     &ShuffleFrogSongRupees,
     &ShuffleAdultTradeQuest,
+    &Shuffle100GSReward,
     &GossipStoneHints,
   };
 
@@ -2720,6 +2742,13 @@ namespace Settings {
     ShuffleMagicBeans.SetSelectedIndex(cvarSettings[RSK_SHUFFLE_MAGIC_BEANS]);
     ShuffleMerchants.SetSelectedIndex(cvarSettings[RSK_SHUFFLE_MERCHANTS]);
 
+    // Force 100 GS Shuffle if that's where Ganon's Boss Key is
+    if (cvarSettings[RSK_GANONS_BOSS_KEY] == RO_GANON_BOSS_KEY_KAK_TOKENS) {
+      Shuffle100GSReward.SetSelectedIndex(1);
+    } else {
+      Shuffle100GSReward.SetSelectedIndex(cvarSettings[RSK_SHUFFLE_100_GS_REWARD]);
+    }
+
     // the  checkbox works because 0 is "Off" and 1 is "Fairy Ocarina"
     StartingOcarina.SetSelectedIndex(cvarSettings[RSK_STARTING_OCARINA]);
     
diff --git a/soh/soh/Enhancements/randomizer/3drando/settings.hpp b/soh/soh/Enhancements/randomizer/3drando/settings.hpp
index 9a51032cf..ed3eb97f6 100644
--- a/soh/soh/Enhancements/randomizer/3drando/settings.hpp
+++ b/soh/soh/Enhancements/randomizer/3drando/settings.hpp
@@ -237,6 +237,7 @@ typedef enum {
     GANONSBOSSKEY_LACS_REWARDS,
     GANONSBOSSKEY_LACS_DUNGEONS,
     GANONSBOSSKEY_LACS_TOKENS,
+    GANONSBOSSKEY_FINAL_GS_REWARD,
 } GanonsBossKeySetting;
 
 typedef enum {
@@ -429,6 +430,7 @@ typedef struct {
     uint8_t shuffleFrogSongRupees;
     uint8_t shuffleAdultTradeQuest;
     uint8_t shuffleChestMinigame;
+    uint8_t shuffle100GsReward;
 
     uint8_t mapsAndCompasses;
     uint8_t keysanity;
@@ -945,6 +947,7 @@ void UpdateSettings(std::unordered_map<RandomizerSettingKey, uint8_t> cvarSettin
   extern Option ShuffleFrogSongRupees;
   extern Option ShuffleAdultTradeQuest;
   extern Option ShuffleChestMinigame;
+  extern Option Shuffle100GSReward;
 
   extern Option MapsAndCompasses;
   extern Option Keysanity;
diff --git a/soh/soh/Enhancements/randomizer/randomizer.cpp b/soh/soh/Enhancements/randomizer/randomizer.cpp
index d40558f63..7dcdc5d30 100644
--- a/soh/soh/Enhancements/randomizer/randomizer.cpp
+++ b/soh/soh/Enhancements/randomizer/randomizer.cpp
@@ -227,6 +227,7 @@ std::unordered_map<std::string, RandomizerSettingKey> SpoilerfileSettingNameToEn
     { "Shuffle Settings:Shuffle Weird Egg", RSK_SHUFFLE_WEIRD_EGG },
     { "Shuffle Settings:Shuffle Frog Song Rupees", RSK_SHUFFLE_FROG_SONG_RUPEES },
     { "Shuffle Settings:Shuffle Merchants", RSK_SHUFFLE_MERCHANTS },
+    { "Shuffle Settings:Shuffle 100 GS Reward", RSK_SHUFFLE_100_GS_REWARD },
     { "Start with Deku Shield", RSK_STARTING_DEKU_SHIELD },
     { "Start with Kokiri Sword", RSK_STARTING_KOKIRI_SWORD },
     { "Start with Fairy Ocarina", RSK_STARTING_OCARINA },
@@ -739,6 +740,7 @@ void Randomizer::ParseRandomizerSettingsFile(const char* spoilerFileName) {
                     case RSK_SHUFFLE_KOKIRI_SWORD:
                     case RSK_SHUFFLE_WEIRD_EGG:
                     case RSK_SHUFFLE_FROG_SONG_RUPEES:
+                    case RSK_SHUFFLE_100_GS_REWARD:
                     case RSK_RANDOM_MQ_DUNGEONS:
                     case RSK_STARTING_DEKU_SHIELD:
                     case RSK_STARTING_KOKIRI_SWORD:
@@ -948,6 +950,8 @@ void Randomizer::ParseRandomizerSettingsFile(const char* spoilerFileName) {
                             gSaveContext.randoSettings[index].value = RO_GANON_BOSS_KEY_LACS_DUNGEONS;
                         } else if(it.value() == "LACS-Tokens") {
                             gSaveContext.randoSettings[index].value = RO_GANON_BOSS_KEY_LACS_TOKENS;
+                        } else if(it.value() == "100 GS Reward") {
+                            gSaveContext.randoSettings[index].value = RO_GANON_BOSS_KEY_KAK_TOKENS;
                         }
                         break;
                     case RSK_SKIP_CHILD_ZELDA:
@@ -2812,6 +2816,7 @@ void GenerateRandomizerImgui() {
     cvarSettings[RSK_SHUFFLE_ADULT_TRADE] = CVarGetInteger("gRandomizeShuffleAdultTrade", 0);
     cvarSettings[RSK_SHUFFLE_MAGIC_BEANS] = CVarGetInteger("gRandomizeShuffleBeans", 0);
     cvarSettings[RSK_SHUFFLE_MERCHANTS] = CVarGetInteger("gRandomizeShuffleMerchants", RO_SHUFFLE_MERCHANTS_OFF);
+    cvarSettings[RSK_SHUFFLE_100_GS_REWARD] = CVarGetInteger("gRandomizeShuffle100GSReward", RO_GENERIC_OFF);
     cvarSettings[RSK_ENABLE_BOMBCHU_DROPS] = CVarGetInteger("gRandomizeEnableBombchuDrops", 0);
     cvarSettings[RSK_BOMBCHUS_IN_LOGIC] = CVarGetInteger("gRandomizeBombchusInLogic", 0);
     cvarSettings[RSK_SKIP_CHILD_ZELDA] = CVarGetInteger("gRandomizeSkipChildZelda", 0);
@@ -2993,10 +2998,11 @@ void DrawRandoEditor(bool& open) {
     static const char* randoShuffleGerudoFortressKeys[4] = { "Vanilla", "Any Dungeon", "Overworld", "Anywhere" };
     static const char* randoShuffleBossKeys[6] = { "Start With",  "Vanilla",   "Own Dungeon",
                                             "Any Dungeon", "Overworld", "Anywhere" };
-    static const char* randoShuffleGanonsBossKey[12] = {"Vanilla", "Own dungeon", "Start with", 
+    static const char* randoShuffleGanonsBossKey[13] = {"Vanilla", "Own dungeon", "Start with", 
                                                 "Any Dungeon", "Overworld", "Anywhere", 
                                                 "LACS-Vanilla", "LACS-Medallions", "LACS-Stones", 
-                                                "LACS-Rewards", "LACS-Dungeons", "LACS-Tokens"};
+                                                "LACS-Rewards", "LACS-Dungeons", "LACS-Tokens",
+                                                "100 GS Reward"};
     static const char* randoShuffleKeyRings[4] = { "Off", "Random", "Count", "Selection" };
 
     // Misc Settings
@@ -3660,6 +3666,22 @@ void DrawRandoEditor(bool& open) {
 
                 UIWidgets::PaddedSeparator();
 
+                // Shuffle 100 GS Reward
+                // Forcefully enabled if Ganon's Boss Key is on the cursed man
+                bool forceEnable100GSShuffle =
+                    (CVarGetInteger("gRandomizeShuffleGanonBossKey", RO_GANON_BOSS_KEY_VANILLA) == RO_GANON_BOSS_KEY_KAK_TOKENS);
+                const char* disable100GSRewardText = "This option is forcefully enabled because \"Ganon's Boss Key\" is set to \"100 GS Reward.\"";
+                UIWidgets::EnhancementCheckbox(Settings::Shuffle100GSReward.GetName().c_str(), "gRandomizeShuffle100GSReward",
+                    forceEnable100GSShuffle, disable100GSRewardText, UIWidgets::CheckboxGraphics::Checkmark);
+                UIWidgets::InsertHelpHoverText(
+                    "Shuffle the item the cursed rich man in the House of Skulltula gives when you "
+                    "have collected all 100 Gold Skulltula Tokens.\n"
+                    "\n"
+                    "You can still talk to him multiple times to get Huge Rupees."
+                );
+
+                UIWidgets::PaddedSeparator();
+
                 ImGui::PopItemWidth();
                 ImGui::EndChild();
 
@@ -3820,7 +3842,9 @@ void DrawRandoEditor(bool& open) {
                     "- Stones: Obtain the specified amount of spiritual stones.\n"
                     "- Dungeon rewards: Obtain the specified total sum of spiritual stones or medallions.\n"
                     "- Dungeons: Complete the specified amount of dungeons. Dungeons are considered complete after stepping in to the blue warp after the boss.\n"
-                    "- Tokens: Obtain the specified amount of Skulltula tokens."
+                    "- Tokens: Obtain the specified amount of Skulltula tokens.\n"
+                    "\n"
+                    "100 GS Reward - Ganon's Boss Key will be awarded by the cursed rich man after you collect 100 Gold Skulltula Tokens."
                 );
                 UIWidgets::EnhancementCombobox("gRandomizeShuffleGanonBossKey", randoShuffleGanonsBossKey, RO_GANON_BOSS_KEY_MAX, RO_GANON_BOSS_KEY_VANILLA);
                 ImGui::PopItemWidth();
diff --git a/soh/soh/Enhancements/randomizer/randomizerTypes.h b/soh/soh/Enhancements/randomizer/randomizerTypes.h
index a8f9a9c14..1a7d5ebe2 100644
--- a/soh/soh/Enhancements/randomizer/randomizerTypes.h
+++ b/soh/soh/Enhancements/randomizer/randomizerTypes.h
@@ -164,6 +164,7 @@ typedef enum {
     RC_KAK_30_GOLD_SKULLTULA_REWARD,
     RC_KAK_40_GOLD_SKULLTULA_REWARD,
     RC_KAK_50_GOLD_SKULLTULA_REWARD,
+    RC_KAK_100_GOLD_SKULLTULA_REWARD,
     RC_KAK_IMPAS_HOUSE_COW,
     RC_KAK_GS_TREE,
     RC_KAK_GS_GUARDS_HOUSE,
@@ -1091,6 +1092,7 @@ typedef enum {
     RSK_STARTING_SKULLTULA_TOKEN,
     RSK_ALL_LOCATIONS_REACHABLE,
     RSK_SHUFFLE_BOSS_ENTRANCES,
+    RSK_SHUFFLE_100_GS_REWARD,
     RSK_MAX
 } RandomizerSettingKey;
 
@@ -1235,7 +1237,7 @@ typedef enum {
 } RandoOptionKeyrings;
 
 //Ganon's Boss Key Settings (vanilla, own dungeon, start with,
-//overworld, anywhere)
+//overworld, anywhere, 100 GS reward)
 typedef enum {
     RO_GANON_BOSS_KEY_VANILLA,
     RO_GANON_BOSS_KEY_OWN_DUNGEON,
@@ -1249,6 +1251,7 @@ typedef enum {
     RO_GANON_BOSS_KEY_LACS_REWARDS,
     RO_GANON_BOSS_KEY_LACS_DUNGEONS,
     RO_GANON_BOSS_KEY_LACS_TOKENS,
+    RO_GANON_BOSS_KEY_KAK_TOKENS,
     RO_GANON_BOSS_KEY_MAX,
 } RandoOptionGanonsBossKey;
 
diff --git a/soh/soh/Enhancements/randomizer/randomizer_check_objects.cpp b/soh/soh/Enhancements/randomizer/randomizer_check_objects.cpp
index 73f9da642..4e561b8d9 100644
--- a/soh/soh/Enhancements/randomizer/randomizer_check_objects.cpp
+++ b/soh/soh/Enhancements/randomizer/randomizer_check_objects.cpp
@@ -220,6 +220,7 @@ std::map<RandomizerCheck, RandomizerCheckObject> rcObjects = {
     RC_OBJECT(RC_KAK_30_GOLD_SKULLTULA_REWARD,                                RCVORMQ_BOTH,    RCTYPE_STANDARD,     RCAREA_KAKARIKO_VILLAGE,       ACTOR_ID_MAX,       SCENE_KINSUTA,                        0x00,                        GI_NONE,             "30 Gold Skulltula Reward", "Kak 30 Gold Skulltula Reward"),
     RC_OBJECT(RC_KAK_40_GOLD_SKULLTULA_REWARD,                                RCVORMQ_BOTH,    RCTYPE_STANDARD,     RCAREA_KAKARIKO_VILLAGE,       ACTOR_ID_MAX,       SCENE_KINSUTA,                        0x00,                        GI_NONE,             "40 Gold Skulltula Reward", "Kak 40 Gold Skulltula Reward"),
     RC_OBJECT(RC_KAK_50_GOLD_SKULLTULA_REWARD,                                RCVORMQ_BOTH,    RCTYPE_STANDARD,     RCAREA_KAKARIKO_VILLAGE,       ACTOR_ID_MAX,       SCENE_KINSUTA,                        0x00,                        GI_NONE,             "50 Gold Skulltula Reward", "Kak 50 Gold Skulltula Reward"),
+    RC_OBJECT(RC_KAK_100_GOLD_SKULLTULA_REWARD,                               RCVORMQ_BOTH,    RCTYPE_STANDARD,     RCAREA_KAKARIKO_VILLAGE,       ACTOR_ID_MAX,       SCENE_KINSUTA,                        0x00,                        GI_NONE,             "100 Gold Skulltula Reward", "Kak 100 Gold Skulltula Reward"),
     RC_OBJECT(RC_KAK_MAN_ON_ROOF,                                             RCVORMQ_BOTH,    RCTYPE_STANDARD,     RCAREA_KAKARIKO_VILLAGE,       ACTOR_ID_MAX,       SCENE_SPOT01,                         0x00,                        GI_NONE,             "Man on Roof", "Kak Man on Roof"),
     RC_OBJECT(RC_KAK_SHOOTING_GALLERY_REWARD,                                 RCVORMQ_BOTH,    RCTYPE_STANDARD,     RCAREA_KAKARIKO_VILLAGE,       ACTOR_ID_MAX,       SCENE_SYATEKIJYOU,                    0x00,                        GI_NONE,             "Shooting Gallery Reward", "Kak Shooting Gallery Reward"),
     RC_OBJECT(RC_KAK_TRADE_ODD_MUSHROOM,                                      RCVORMQ_BOTH,    RCTYPE_ADULT_TRADE,  RCAREA_KAKARIKO_VILLAGE,       ACTOR_ID_MAX,       SCENE_MAHOUYA,                        0x00,                        GI_NONE,             "Trade Odd Mushroom", "Kak Trade Odd Mushroom"),
diff --git a/soh/soh/Enhancements/randomizer/randomizer_inf.h b/soh/soh/Enhancements/randomizer/randomizer_inf.h
index b49165e37..fa862fe9d 100644
--- a/soh/soh/Enhancements/randomizer/randomizer_inf.h
+++ b/soh/soh/Enhancements/randomizer/randomizer_inf.h
@@ -149,6 +149,8 @@ typedef enum {
     RAND_INF_ADULT_TRADES_LH_TRADE_FROG,
     RAND_INF_ADULT_TRADES_DMT_TRADE_EYEDROPS,
 
+    RAND_INF_KAK_100_GOLD_SKULLTULA_REWARD,
+
     // If you add anything to this list, you need to update the size of randomizerInf in z64save.h to be ceil(RAND_INF_MAX / 16)
 
     RAND_INF_MAX,
diff --git a/soh/src/overlays/actors/ovl_En_Sth/z_en_sth.c b/soh/src/overlays/actors/ovl_En_Sth/z_en_sth.c
index cdfd90efc..064de26fe 100644
--- a/soh/src/overlays/actors/ovl_En_Sth/z_en_sth.c
+++ b/soh/src/overlays/actors/ovl_En_Sth/z_en_sth.c
@@ -244,6 +244,10 @@ void EnSth_GivePlayerItem(EnSth* this, PlayState* play) {
     if (gSaveContext.n64ddFlag) {
         switch (getItemId) {
             case GI_RUPEE_GOLD:
+                if (!Flags_GetRandomizerInf(RAND_INF_KAK_100_GOLD_SKULLTULA_REWARD)) {
+                    getItemEntry = Randomizer_GetItemFromKnownCheck(RC_KAK_100_GOLD_SKULLTULA_REWARD, GI_RUPEE_GOLD);
+                    Flags_SetRandomizerInf(RAND_INF_KAK_100_GOLD_SKULLTULA_REWARD);
+                }
                 break;
             case GI_WALLET_ADULT:
                 getItemEntry = Randomizer_GetItemFromKnownCheck(RC_KAK_10_GOLD_SKULLTULA_REWARD, GI_WALLET_ADULT);