diff --git a/include/battle_ai_util.h b/include/battle_ai_util.h
index e6d99f2eed..0800e1cfb8 100644
--- a/include/battle_ai_util.h
+++ b/include/battle_ai_util.h
@@ -168,7 +168,7 @@ bool32 PartnerMoveIsSameNoTarget(u8 battlerAtkPartner, u16 move, u16 partnerMove
 bool32 ShouldUseWishAromatherapy(u8 battlerAtk, u8 battlerDef, u16 move);
 
 // party logic
-s32 AI_CalcPartyMonDamage(u16 move, u8 battlerAtk, u8 battlerDef, struct Pokemon *mon);
+s32 AI_CalcPartyMonBestMoveDamage(u32 battlerAtk, u32 battlerDef, struct Pokemon *attackerMon, struct Pokemon *targetMon);
 s32 CountUsablePartyMons(u8 battlerId);
 bool32 IsPartyFullyHealedExceptBattler(u8 battler);
 bool32 PartyHasMoveSplit(u8 battlerId, u8 split);
diff --git a/src/battle_ai_switch_items.c b/src/battle_ai_switch_items.c
index 73d7ecb645..2418dbab85 100644
--- a/src/battle_ai_switch_items.c
+++ b/src/battle_ai_switch_items.c
@@ -28,6 +28,7 @@ static bool8 ShouldUseItem(void);
 static bool32 AiExpectsToFaintPlayer(void);
 static bool32 AI_ShouldHeal(u32 healAmount);
 static bool32 AI_OpponentCanFaintAiWithMod(u32 healAmount);
+static bool32 IsAiPartyMonOHKOBy(u32 battlerAtk, struct Pokemon *aiMon);
 
 static bool32 IsAceMon(u32 battlerId, u32 monPartyId)
 {
@@ -753,6 +754,8 @@ void AI_TrySwitchOrUseItem(void)
                     {
                         if (GetMonData(&party[monToSwitchId], MON_DATA_HP) == 0)
                             continue;
+                        if (GetMonData(&party[monToSwitchId], MON_DATA_SPECIES) == SPECIES_NONE)
+                            continue;
                         if (monToSwitchId == gBattlerPartyIndexes[battlerIn1])
                             continue;
                         if (monToSwitchId == gBattlerPartyIndexes[battlerIn2])
@@ -793,6 +796,8 @@ static u32 GetBestMonBatonPass(struct Pokemon *party, int firstId, int lastId, u
     {
         if (invalidMons & gBitTable[i])
             continue;
+        if (IsAiPartyMonOHKOBy(BATTLE_OPPOSITE(gActiveBattler), &party[i]))
+            continue;
 
         for (j = 0; j < MAX_MON_MOVES; j++)
         {
@@ -837,6 +842,9 @@ static u32 GetBestMonTypeMatchup(struct Pokemon *party, int firstId, int lastId,
                 u8 defType1 = gSpeciesInfo[species].types[0];
                 u8 defType2 = gSpeciesInfo[species].types[1];
 
+                if (IsAiPartyMonOHKOBy(opposingBattler, &party[i]))
+                    continue;
+
                 typeEffectiveness = uq4_12_multiply(typeEffectiveness, (GetTypeModifier(atkType1, defType1)));
                 if (atkType2 != atkType1)
                     typeEffectiveness = uq4_12_multiply(typeEffectiveness, (GetTypeModifier(atkType2, defType1)));
@@ -881,7 +889,7 @@ static u32 GetBestMonTypeMatchup(struct Pokemon *party, int firstId, int lastId,
 static u32 GetBestMonDmg(struct Pokemon *party, int firstId, int lastId, u8 invalidMons, u32 opposingBattler)
 {
     int i, j;
-    int bestDmg = 0;
+    int dmg, bestDmg = 0;
     int bestMonId = PARTY_SIZE;
 
     gMoveResultFlags = 0;
@@ -890,19 +898,14 @@ static u32 GetBestMonDmg(struct Pokemon *party, int firstId, int lastId, u8 inva
     {
         if (gBitTable[i] & invalidMons)
             continue;
+        if (IsAiPartyMonOHKOBy(opposingBattler, &party[i]))
+            continue;
 
-        for (j = 0; j < MAX_MON_MOVES; j++)
+        dmg = AI_CalcPartyMonBestMoveDamage(gActiveBattler, opposingBattler, &party[i], NULL);
+        if (bestDmg < dmg)
         {
-            u32 move = GetMonData(&party[i], MON_DATA_MOVE1 + j);
-            if (move != MOVE_NONE && gBattleMoves[move].power != 0)
-            {
-                s32 dmg = AI_CalcPartyMonDamage(move, gActiveBattler, opposingBattler, &party[i]);
-                if (bestDmg < dmg)
-                {
-                    bestDmg = dmg;
-                    bestMonId = i;
-                }
-            }
+            bestDmg = dmg;
+            bestMonId = i;
         }
     }
 
@@ -912,7 +915,7 @@ static u32 GetBestMonDmg(struct Pokemon *party, int firstId, int lastId, u8 inva
 u8 GetMostSuitableMonToSwitchInto(void)
 {
     u32 opposingBattler = 0;
-    u32 bestMonId = 0;
+    u32 bestMonId = PARTY_SIZE;
     u8 battlerIn1 = 0, battlerIn2 = 0;
     s32 firstId = 0;
     s32 lastId = 0; // + 1
@@ -1155,3 +1158,20 @@ static bool32 AI_OpponentCanFaintAiWithMod(u32 healAmount)
     }
     return FALSE;
 }
+
+static bool32 IsAiPartyMonOHKOBy(u32 battlerAtk, struct Pokemon *aiMon)
+{
+    struct BattlePokemon *battleMon;
+    s32 hp = GetMonData(aiMon, MON_DATA_HP);
+    s32 bestDmg = AI_CalcPartyMonBestMoveDamage(battlerAtk, gActiveBattler, NULL, aiMon);
+
+    switch (GetNoOfHitsToKO(bestDmg, hp))
+    {
+    case 1:
+        return TRUE;
+    case 2: // TODO: Compare speeds, if AI mon is faster allow 2 turns
+        return TRUE;
+    }
+
+    return FALSE;
+}
diff --git a/src/battle_ai_util.c b/src/battle_ai_util.c
index 3e8c5ae87b..036e9e4f61 100644
--- a/src/battle_ai_util.c
+++ b/src/battle_ai_util.c
@@ -3369,24 +3369,40 @@ bool32 ShouldUseWishAromatherapy(u8 battlerAtk, u8 battlerDef, u16 move)
 }
 
 // party logic
-s32 AI_CalcPartyMonDamage(u16 move, u8 battlerAtk, u8 battlerDef, struct Pokemon *mon)
+s32 AI_CalcPartyMonBestMoveDamage(u32 battlerAtk, u32 battlerDef, struct Pokemon *attackerMon, struct Pokemon *targetMon)
 {
-    s32 dmg;
-    u32 i;
+    s32 bestDmg, dmg;
+    u32 i, move;
     u8 effectiveness;
     struct BattlePokemon *battleMons = Alloc(sizeof(struct BattlePokemon) * MAX_BATTLERS_COUNT);
 
     for (i = 0; i < MAX_BATTLERS_COUNT; i++)
         battleMons[i] = gBattleMons[i];
 
-    PokemonToBattleMon(mon, &gBattleMons[battlerAtk]);
-    dmg = AI_CalcDamage(move, battlerAtk, battlerDef, &effectiveness, FALSE);
+    if (attackerMon != NULL)
+        PokemonToBattleMon(attackerMon, &gBattleMons[battlerAtk]);
+    if (targetMon != NULL)
+        PokemonToBattleMon(targetMon, &gBattleMons[battlerDef]);
+
+    for (bestDmg = 0, i = 0; i < MAX_MON_MOVES; i++)
+    {
+        if (BattlerHasAi(battlerAtk))
+            move = GetMonData(attackerMon, MON_DATA_MOVE1 + i);
+        else
+            move = AI_PARTY->mons[GET_BATTLER_SIDE2(battlerAtk)][gBattlerPartyIndexes[battlerAtk]].moves[i];
+
+        if (move != MOVE_NONE && gBattleMoves[move].power != 0)
+        {
+            dmg = AI_CalcDamage(move, battlerAtk, battlerDef, &effectiveness, FALSE);
+            if (dmg > bestDmg)
+                bestDmg = dmg;
+        }
+    }
 
     for (i = 0; i < MAX_BATTLERS_COUNT; i++)
         gBattleMons[i] = battleMons[i];
 
     Free(battleMons);
-
     return dmg;
 }
 
diff --git a/src/battle_controller_opponent.c b/src/battle_controller_opponent.c
index f316f19ea8..4b8820f9b9 100644
--- a/src/battle_controller_opponent.c
+++ b/src/battle_controller_opponent.c
@@ -1688,7 +1688,6 @@ static void OpponentHandleChoosePokemon(void)
     else if (*(gBattleStruct->AI_monToSwitchIntoId + gActiveBattler) == PARTY_SIZE)
     {
         chosenMonId = GetMostSuitableMonToSwitchInto();
-
         if (chosenMonId == PARTY_SIZE)
         {
             s32 battler1, battler2, firstId, lastId;
@@ -1702,7 +1701,6 @@ static void OpponentHandleChoosePokemon(void)
                 battler1 = GetBattlerAtPosition(B_POSITION_OPPONENT_LEFT);
                 battler2 = GetBattlerAtPosition(B_POSITION_OPPONENT_RIGHT);
                 pokemonInBattle = 2;
-
             }
 
             GetAIPartyIndexes(gActiveBattler, &firstId, &lastId);
@@ -1710,6 +1708,7 @@ static void OpponentHandleChoosePokemon(void)
             for (chosenMonId = (lastId-1); chosenMonId >= firstId; chosenMonId--)
             {
                 if (GetMonData(&gEnemyParty[chosenMonId], MON_DATA_HP) != 0
+                    && GetMonData(&gEnemyParty[chosenMonId], MON_DATA_SPECIES) != SPECIES_NONE
                     && chosenMonId != gBattlerPartyIndexes[battler1]
                     && chosenMonId != gBattlerPartyIndexes[battler2]
                     && (!(AI_THINKING_STRUCT->aiFlags & AI_FLAG_ACE_POKEMON)
diff --git a/src/data/trainer_parties.h b/src/data/trainer_parties.h
index 1759120b7f..a0e45ca0c6 100644
--- a/src/data/trainer_parties.h
+++ b/src/data/trainer_parties.h
@@ -3366,25 +3366,39 @@ static const struct TrainerMonItemCustomMoves sParty_Drake[] = {
 
 static const struct TrainerMonItemCustomMoves sParty_Roxanne1[] = {
     {
-    .iv = 100,
-    .lvl = 12,
-    .species = SPECIES_GEODUDE,
+    .iv = 46,
+    .lvl = 46,
+    .species = SPECIES_SKARMORY,
     .heldItem = ITEM_NONE,
-    .moves = {MOVE_TACKLE, MOVE_DEFENSE_CURL, MOVE_ROCK_THROW, MOVE_ROCK_TOMB}
+    .moves = {MOVE_SPIKES, MOVE_TOXIC, MOVE_WHIRLWIND, MOVE_ROOST}
     },
     {
     .iv = 100,
-    .lvl = 12,
-    .species = SPECIES_GEODUDE,
+    .lvl = 46,
+    .species = SPECIES_TROPIUS,
     .heldItem = ITEM_NONE,
-    .moves = {MOVE_TACKLE, MOVE_DEFENSE_CURL, MOVE_ROCK_THROW, MOVE_ROCK_TOMB}
+    .moves = {MOVE_LEAF_TORNADO, MOVE_BODY_SLAM, MOVE_PROTECT, MOVE_ROOST}
+    },
+    {
+    .iv = 47,
+    .lvl = 47,
+    .species = SPECIES_HAWLUCHA,
+    .heldItem = ITEM_ORAN_BERRY,
+    .moves = {MOVE_SUPERPOWER, MOVE_ACROBATICS, MOVE_U_TURN, MOVE_ROOST}
+    },
+    {
+    .iv = 47,
+    .lvl = 47,
+    .species = SPECIES_MANTINE,
+    .heldItem = ITEM_ORAN_BERRY,
+    .moves = {MOVE_CONFUSE_RAY, MOVE_WATER_PULSE, MOVE_AIR_SLASH, MOVE_ROOST}
     },
     {
     .iv = 200,
-    .lvl = 15,
-    .species = SPECIES_NOSEPASS,
+    .lvl = 48,
+    .species = SPECIES_ALTARIA,
     .heldItem = ITEM_ORAN_BERRY,
-    .moves = {MOVE_BLOCK, MOVE_HARDEN, MOVE_TACKLE, MOVE_ROCK_TOMB}
+    .moves = {MOVE_DRAGON_PULSE, MOVE_TOXIC, MOVE_COTTON_GUARD, MOVE_ROOST}
     }
 };
 
diff --git a/src/data/trainers.h b/src/data/trainers.h
index 75f7edc8b7..22d4a48804 100644
--- a/src/data/trainers.h
+++ b/src/data/trainers.h
@@ -3189,7 +3189,7 @@ const struct Trainer gTrainers[] = {
         .trainerName = _("ROXANNE"),
         .items = {ITEM_POTION, ITEM_POTION, ITEM_NONE, ITEM_NONE},
         .doubleBattle = FALSE,
-        .aiFlags = AI_FLAG_CHECK_BAD_MOVE | AI_FLAG_TRY_TO_FAINT | AI_FLAG_CHECK_VIABILITY,
+        .aiFlags = AI_FLAG_CHECK_BAD_MOVE | AI_FLAG_TRY_TO_FAINT | AI_FLAG_CHECK_VIABILITY | AI_FLAG_RISKY,
         .party = ITEM_CUSTOM_MOVES(sParty_Roxanne1),
     },