diff --git a/soh/src/code/z_parameter.c b/soh/src/code/z_parameter.c
index 20debfd79..a4d61f877 100644
--- a/soh/src/code/z_parameter.c
+++ b/soh/src/code/z_parameter.c
@@ -1521,6 +1521,13 @@ void Inventory_SwapAgeEquipment(void) {
                 }
             }
 
+            // In Rando, when switching to adult for the second+ time, if a sword was not previously
+            // equiped in MS shuffle, then we need to set the swordless flag again
+            if (IS_RANDO && Randomizer_GetSettingValue(RSK_SHUFFLE_MASTER_SWORD) &&
+                gSaveContext.equips.buttonItems[0] == ITEM_NONE) {
+                Flags_SetInfTable(INFTABLE_SWORDLESS);
+            }
+
             gSaveContext.equips.equipment = gSaveContext.adultEquips.equipment;
         }
     } else {
@@ -1589,6 +1596,13 @@ void Inventory_SwapAgeEquipment(void) {
                 }
             }
 
+            // In Rando, when switching to child from a swordless adult, and child Link previously had a
+            // sword equiped, then we need to unset the swordless flag to match
+            if (IS_RANDO && Randomizer_GetSettingValue(RSK_SHUFFLE_MASTER_SWORD) &&
+                gSaveContext.equips.buttonItems[0] != ITEM_NONE) {
+                Flags_UnsetInfTable(INFTABLE_SWORDLESS);
+            }
+
             gSaveContext.equips.equipment = gSaveContext.childEquips.equipment;
             gSaveContext.equips.equipment &= (u16) ~(0xF << (EQUIP_TYPE_SWORD * 4));
             gSaveContext.equips.equipment |= EQUIP_VALUE_SWORD_KOKIRI << (EQUIP_TYPE_SWORD * 4);