diff --git a/include/d/d_item.h b/include/d/d_item.h
index 23787a7340..533908bc6c 100644
--- a/include/d/d_item.h
+++ b/include/d/d_item.h
@@ -526,6 +526,9 @@ int checkItemGet(u8, int);
 BOOL isHeart(u8 item_no);
 int isBomb(u8);
 int isArrow(u8);
+#if TARGET_PC
+int isRupee(u8);
+#endif
 int addBombCount(u8, u8);
 BOOL isBottleItem(u8 item_no);
 u8 check_itemno(int i_itemNo);
diff --git a/src/d/actor/d_a_obj_item.cpp b/src/d/actor/d_a_obj_item.cpp
index 73c134e559..ae8d2263ea 100644
--- a/src/d/actor/d_a_obj_item.cpp
+++ b/src/d/actor/d_a_obj_item.cpp
@@ -613,7 +613,8 @@ void daItem_c::procWaitGetDemoEvent() {
 
             procInitSimpleGetDemo();
             itemGet();
-            if (!haveItem) {
+            // Don't potentially unset item bits in rando unless they're rupees
+            if (!haveItem IF_DUSK(&& (!randomizer_IsActive() || isRupee(m_itemNo)))) {
                 dComIfGs_offItemFirstBit(m_itemNo);
             }
         } else {
diff --git a/src/d/d_item.cpp b/src/d/d_item.cpp
index bdc70ddd21..ab0ea890e9 100644
--- a/src/d/d_item.cpp
+++ b/src/d/d_item.cpp
@@ -3355,6 +3355,25 @@ BOOL isHeart(u8 i_itemNo) {
     return is_heart;
 }
 
+#if TARGET_PC
+BOOL isRupee(u8 i_itemNo) {
+    switch (i_itemNo) {
+    case dItemNo_GREEN_RUPEE_e:
+    case dItemNo_BLUE_RUPEE_e:
+    case dItemNo_YELLOW_RUPEE_e:
+    case dItemNo_RED_RUPEE_e:
+    case dItemNo_PURPLE_RUPEE_e:
+    case dItemNo_ORANGE_RUPEE_e:
+    case dItemNo_SILVER_RUPEE_e:
+        return true;
+    default:
+        break;
+    }
+
+    return false;
+}
+#endif
+
 BOOL isInsect(u8 i_itemNo) {
     BOOL is_insect = false;