diff --git a/src/battle_ai_main.c b/src/battle_ai_main.c
index 317f79d977..1dcb86805d 100644
--- a/src/battle_ai_main.c
+++ b/src/battle_ai_main.c
@@ -4111,10 +4111,14 @@ static s16 AI_CheckViability(u8 battlerAtk, u8 battlerDef, u16 move, s16 score)
         if (AI_DATA->atkAbility == ABILITY_RIPEN)
         {
             u16 item = GetUsedHeldItem(battlerAtk);
+            u16 toHeal = (ItemId_GetHoldEffectParam(item) == 10) ? 10 : gBattleMons[battlerAtk].maxHP / ItemId_GetHoldEffectParam(item);
+            
             if (IsStatBoostingBerry(item) && atkHpPercent > 60)
                 score++;
-            else if (IsHpRestoringBerry(item) && atkHpPercent < 60)
-                score++;    // TODO check if player can still faint us after we heal
+            else if (IsHpRestoringBerry(item) && !CanAIFaintTarget(battlerAtk, battlerDef, 0) 
+              && ((GetWhoStrikesFirst(battlerAtk, battlerDef, TRUE) == 0 && CanTargetFaintAiWithMod(battlerDef, battlerAtk, 0, 0))
+               || !CanTargetFaintAiWithMod(battlerDef, battlerAtk, toheal, 0)))
+                score++;    // Recycle healing berry if we can't otherwise faint the target and the target wont kill us after we activate the berry
         }
         break;
     case EFFECT_BRICK_BREAK:
diff --git a/src/battle_ai_util.c b/src/battle_ai_util.c
index 19dfab8577..dc85901e32 100644
--- a/src/battle_ai_util.c
+++ b/src/battle_ai_util.c
@@ -3389,11 +3389,14 @@ bool32 IsStatBoostingBerry(u16 item)
     }
 }
 
-bool32 IsHpRestoringBerry(u16 item)
+bool32 IsHpRestoringBerry(u8 battlerAtk, u16 item)
 {
     switch (item)
     {
     case ITEM_ORAN_BERRY:
+        if (gBattleMons[battlerAtk].maxHp <= 50)
+            return TRUE;    // Only worth it in the early game
+        return FALSE;
     case ITEM_SITRUS_BERRY:
     case ITEM_FIGY_BERRY:
     case ITEM_WIKI_BERRY: