diff --git a/src/d/actor/d_a_b_ds.cpp b/src/d/actor/d_a_b_ds.cpp
index 3ecba6f4a1..6aad3f323a 100644
--- a/src/d/actor/d_a_b_ds.cpp
+++ b/src/d/actor/d_a_b_ds.cpp
@@ -4089,6 +4089,8 @@ void daB_DS_c::executeBattle2Dead() {
                 // Give the boss item
                 u8 agDungeonReward = randomizer_getItemAtLocation("Arbiters Grounds Dungeon Reward");
                 g_randomizerState.addItemToEventQueue(agDungeonReward);
+                // Set custom item flag
+                dComIfGs_onItem(0x9E, -1);
             }
 #endif
             /* dSv_event_flag_c::F_0265 - Arbiter's Grounds - Arbiter's Grounds clear */
diff --git a/src/d/actor/d_a_obj_life_container.cpp b/src/d/actor/d_a_obj_life_container.cpp
index dec5ae27bd..231525b5e6 100644
--- a/src/d/actor/d_a_obj_life_container.cpp
+++ b/src/d/actor/d_a_obj_life_container.cpp
@@ -224,6 +224,8 @@ int daObjLife_c::create() {
             } else if (getStageID() == Ook) {
                 // Special case for Gale Boomerang check
                 itemId = verifyProgressiveItem(randomizer_getItemAtLocation("Forest Temple Gale Boomerang"));
+                // Set rando custom collection flag
+                dComIfGs_onItem(0x9D, -1);
             } else {
                 u8 flag = getSaveBitNo();
                 u8 stageIdx = getStageID();
diff --git a/src/dusk/randomizer/game/randomizer_context.cpp b/src/dusk/randomizer/game/randomizer_context.cpp
index 0451e3fb84..e059e9246f 100644
--- a/src/dusk/randomizer/game/randomizer_context.cpp
+++ b/src/dusk/randomizer/game/randomizer_context.cpp
@@ -781,10 +781,17 @@ static void randomizer_setTempFlag(RandomizerContext::itemLocationData data) {
     // If stage is 0xFF, then this is an event flag
     if (data.stage == 0xFF) {
         g_randomizerState.mTrackerTempEventFlag = data.flag;
-    } else {
+    }
+    // If it's less than 0x80 then it's a switch flag
+    else if (data.flag < 0x80) {
         g_randomizerState.mTrackerTempSwitchFlag.stage = getStageSaveId(data.stage);
         g_randomizerState.mTrackerTempSwitchFlag.flag = data.flag;
     }
+    // Otherwise it's an item flag. Currently, any item flags that go through here are custom
+    // so we just set the bit directly.
+    else {
+        dComIfGs_onItem(data.flag, getStageSaveId(data.stage));
+    }
 }
 
 void randomizer_setTempFlagForLocation(const std::string& locationName) {
@@ -1061,6 +1068,9 @@ RandomizerContext WriteSeedData(randomizer::logic::world::World* world) {
             } else if (metaData["Switch Flag"]) {
                 itemData.stage = metaData["Switch Flag"]["Stage"].as<u8>();
                 itemData.flag = metaData["Switch Flag"]["Flag"].as<u8>();
+            } else if (metaData["Item Flag"]) {
+                itemData.stage = metaData["Item Flag"]["Stage"].as<u8>();
+                itemData.flag = metaData["Item Flag"]["Flag"].as<u8>();
             }
         };
 
diff --git a/src/dusk/randomizer/game/tools.cpp b/src/dusk/randomizer/game/tools.cpp
index 112e99c52c..c5ffe150b3 100644
--- a/src/dusk/randomizer/game/tools.cpp
+++ b/src/dusk/randomizer/game/tools.cpp
@@ -504,6 +504,11 @@ bool isLocationObtained(randomizer::logic::location::Location* location) {
         auto stageId = getStageSaveId(switchFlagNode["Stage"].as<u8>());
         return tracker_isStageSwitch(stageId, flag);
     }
+    if (auto& itemFlagNode = locationMeta["Item Flag"]) {
+        auto flag = itemFlagNode["Flag"].as<u8>();
+        auto stageId = getStageSaveId(itemFlagNode["Stage"].as<u8>());
+        return tracker_isStageItem(stageId, flag);
+    }
     return false;
 }
 
@@ -546,7 +551,7 @@ int getLocationItem(randomizer::logic::location::Location* location) {
         return context.mSkyCharacterOverrides[key];
     }
     if (auto& bugRewardNode = locationMeta["Bug Reward"]) {
-        u8 bugItemId = bugRewardNode["Item Id"].as<u8>();
+        u8 bugItemId = bugRewardNode[0]["Item Id"].as<u8>();
         return context.mBugRewardOverrides[bugItemId];
     }
 
diff --git a/src/dusk/randomizer/generator/data/locations.yaml b/src/dusk/randomizer/generator/data/locations.yaml
index 11bba31382..975a23f1b4 100644
--- a/src/dusk/randomizer/generator/data/locations.yaml
+++ b/src/dusk/randomizer/generator/data/locations.yaml
@@ -4790,9 +4790,9 @@
   Metadata:
     Name Lookup:
       - Forest Temple Gale Boomerang
-    Switch Flag:
+    Item Flag:
       Stage: 8
-      Flag: 0x59
+      Flag: 0x9D
 
 - Name: Forest Temple Big Key Chest
   Original Item: Forest Temple Big Key
@@ -4890,7 +4890,9 @@
     FLW Message:
       - Group: 5
         Message Id: 5001
-    Event Flag: 0x0602 # late
+    Item Flag:
+      Stage: 7
+      Flag: 0x9E
 
 # GORON MINES
 
@@ -5754,7 +5756,9 @@
   Metadata:
     Name Lookup:
       - Arbiters Grounds Dungeon Reward
-    Event Flag: 0x2010
+    Item Flag:
+      Stage: 25
+      Flag: 0x9E
 
 # SNOWPEAK RUINS
 
@@ -6278,7 +6282,9 @@
     FLW Message:
       - Group: 5
         Message Id: 9401
-    Event Flag: 0x2004
+    Item Flag:
+      Stage: 10
+      Flag: 0x9E
 
 # CITY IN THE SKY