diff --git a/soh/soh/GameMenuBar.cpp b/soh/soh/GameMenuBar.cpp
index 15aece0f2..f7cc97993 100644
--- a/soh/soh/GameMenuBar.cpp
+++ b/soh/soh/GameMenuBar.cpp
@@ -24,6 +24,7 @@
 
 #include "UIWidgets.hpp"
 #include "include/z64audio.h"
+#include "soh/SaveManager.h"
 
 #define EXPERIMENTAL() \
     ImGui::PushStyleColor(ImGuiCol_Text, IM_COL32(255, 50, 50, 255)); \
@@ -157,6 +158,8 @@ namespace GameMenuBar {
         CVar_SetS32("gBombchuDrops", 0);
         // Always Win Goron Pot
         CVar_SetS32("gGoronPot", 0);
+        // Always Win Dampe Digging First Try
+        CVar_SetS32("gDampeWin", 0);
 
         // Change Red Potion Effect
         CVar_SetS32("gRedPotionEffect", 0);
@@ -379,6 +382,8 @@ namespace GameMenuBar {
         CVar_SetS32("gFastBoomerang", 1);
         // Mask Select in Inventory
         CVar_SetS32("gMaskSelect", 1);
+        // Always Win Dampe Digging
+        CVar_SetS32("gDampeWin", 1);
 
         // Disable Navi Call Audio
         CVar_SetS32("gDisableNaviCallAudio", 1);
@@ -775,6 +780,9 @@ namespace GameMenuBar {
                     UIWidgets::Tooltip("Disables heart drops, but not heart placements, like from a Deku Scrub running off\nThis simulates Hero Mode from other games in the series");
                     UIWidgets::PaddedEnhancementCheckbox("Always Win Goron Pot", "gGoronPot", true, false);
                     UIWidgets::Tooltip("Always get the heart piece/purple rupee from the spinning Goron pot");
+                    UIWidgets::PaddedEnhancementCheckbox("Always Win Dampe Digging Game", "gDampeWin", true, false, SaveManager::Instance->IsRandoFile(),
+                                                         "This setting is always enabled in randomizer files", UIWidgets::CheckboxGraphics::Checkmark);
+                    UIWidgets::Tooltip("Always win the heart piece/purple rupee on the first dig in Dampe's grave digging game, just like in rando\nIn a rando file, this is unconditionally enabled");
                     UIWidgets::Spacer(0);
 
                     if (ImGui::BeginMenu("Potion Values"))
diff --git a/soh/soh/SaveManager.cpp b/soh/soh/SaveManager.cpp
index 52cba1f5e..d1078a4da 100644
--- a/soh/soh/SaveManager.cpp
+++ b/soh/soh/SaveManager.cpp
@@ -1214,6 +1214,10 @@ void SaveManager::DeleteZeldaFile(int fileNum) {
     fileMetaInfo[fileNum].randoSave = false;
 }
 
+bool SaveManager::IsRandoFile() {
+    return gSaveContext.n64ddFlag != 0 ? true : false;
+}
+
 // Functionality required to convert old saves into versioned saves
 
 // DO NOT EDIT ANY OF THE FOLLOWING STRUCTS
diff --git a/soh/soh/SaveManager.h b/soh/soh/SaveManager.h
index 1acbcbfc9..4bef01e69 100644
--- a/soh/soh/SaveManager.h
+++ b/soh/soh/SaveManager.h
@@ -57,6 +57,7 @@ public:
 
     void CopyZeldaFile(int from, int to);
     void DeleteZeldaFile(int fileNum);
+    bool IsRandoFile();
 
     // Use a name of "" to save to an array. You must be in a SaveArray callback.
     template<typename T>
diff --git a/soh/src/overlays/actors/ovl_En_Tk/z_en_tk.c b/soh/src/overlays/actors/ovl_En_Tk/z_en_tk.c
index 11530b07e..920a8feea 100644
--- a/soh/src/overlays/actors/ovl_En_Tk/z_en_tk.c
+++ b/soh/src/overlays/actors/ovl_En_Tk/z_en_tk.c
@@ -408,7 +408,7 @@ s32 EnTk_ChooseReward(EnTk* this) {
     f32 luck;
     s32 reward;
 
-    if (gSaveContext.n64ddFlag && !Flags_GetCollectible(gGlobalCtx, 0x1F) && this->heartPieceSpawned == 0) {
+    if ((gSaveContext.n64ddFlag || CVar_GetS32("gDampeWin", 0)) && !Flags_GetCollectible(gGlobalCtx, 0x1F) && this->heartPieceSpawned == 0) {
         return 3;
     }
 
@@ -604,7 +604,7 @@ void EnTk_Dig(EnTk* this, GlobalContext* globalCtx) {
 
         this->rewardTimer = 0;
 
-        if (this->validDigHere == 1 || gSaveContext.n64ddFlag) {
+        if (this->validDigHere == 1 || gSaveContext.n64ddFlag || CVar_GetS32("gDampeWin", 0)) {
             rewardOrigin.x = 0.0f;
             rewardOrigin.y = 0.0f;
             rewardOrigin.z = -40.0f;
@@ -620,21 +620,21 @@ void EnTk_Dig(EnTk* this, GlobalContext* globalCtx) {
 
             // merging in dampe tour fix seems messy, so i'm just wrapping this whole thing
             // in an n64dd check for now
-            if(gSaveContext.n64ddFlag) {
+            if (gSaveContext.n64ddFlag || CVar_GetS32("gDampeWin", 0)) {
                 if (this->currentReward == 3) {
                     /*
                     * Upgrade the purple rupee reward to the heart piece if this
                     * is the first grand prize dig.
                     */
-                    if (!(gSaveContext.itemGetInf[1] & 0x1000) && !gSaveContext.n64ddFlag) {
+                    if (!(gSaveContext.itemGetInf[1] & 0x1000) && !(gSaveContext.n64ddFlag || CVar_GetS32("gDampeWin", 0))) {
                         gSaveContext.itemGetInf[1] |= 0x1000;
                         this->currentReward = 4;
-                    } else if (gSaveContext.n64ddFlag && !Flags_GetCollectible(gGlobalCtx, 0x1F) && this->heartPieceSpawned == 0) {
+                    } else if ((gSaveContext.n64ddFlag || CVar_GetS32("gDampeWin", 0)) && !Flags_GetCollectible(gGlobalCtx, 0x1F) && this->heartPieceSpawned == 0) {
                         this->currentReward = 4;
                     }
                 }
 
-                if (gSaveContext.n64ddFlag && this->currentReward == 4) {
+                if ((gSaveContext.n64ddFlag || CVar_GetS32("gDampeWin", 0)) && this->currentReward == 4) {
                     Actor_Spawn(&globalCtx->actorCtx, globalCtx, ACTOR_EN_ITEM00, rewardPos.x, rewardPos.y, rewardPos.z, 0,
                                 0, 0, 0x1F06);
                     this->heartPieceSpawned = 1;
@@ -670,7 +670,7 @@ void EnTk_Dig(EnTk* this, GlobalContext* globalCtx) {
 
     if (this->skelAnime.curFrame >= 32.0f && this->rewardTimer == 10) {
         /* Play a reward sound shortly after digging */
-        if (!gSaveContext.n64ddFlag && this->validDigHere == 0) {
+        if (!(gSaveContext.n64ddFlag || CVar_GetS32("gDampeWin", 0)) && this->validDigHere == 0) {
             /* Bad dig spot */
             Audio_PlayActorSound2(&this->actor, NA_SE_SY_ERROR);
         } else if (this->currentReward == 4) {