diff --git a/plugin/src/main/java/com/denizenscript/denizen/scripts/commands/entity/LookCommand.java b/plugin/src/main/java/com/denizenscript/denizen/scripts/commands/entity/LookCommand.java
index 2515dc1d84..50de0d3a62 100644
--- a/plugin/src/main/java/com/denizenscript/denizen/scripts/commands/entity/LookCommand.java
+++ b/plugin/src/main/java/com/denizenscript/denizen/scripts/commands/entity/LookCommand.java
@@ -23,11 +23,14 @@
 import com.denizenscript.denizencore.scripts.commands.generator.ArgPrefixed;
 import com.denizenscript.denizencore.utilities.Deprecations;
 import com.denizenscript.denizencore.utilities.debugging.Debug;
+import org.bukkit.Bukkit;
 import org.bukkit.Location;
+import org.bukkit.entity.Entity;
 import org.bukkit.entity.Player;
 import org.bukkit.event.player.PlayerTeleportEvent;
 import org.bukkit.scheduler.BukkitRunnable;
 import org.bukkit.scheduler.BukkitTask;
+import org.bukkit.util.Vector;
 
 import java.util.Arrays;
 import java.util.HashMap;
@@ -125,37 +128,52 @@ public static void autoExecute(ScriptEntry scriptEntry,
         final float pitchRaw = pitch == null ? 0 : pitch.asFloat();
         for (EntityTag entity : entities) {
             if (entity.isSpawned()) {
+                Entity bukkitEntity = entity.getBukkitEntity();
+                Entity vehicle = bukkitEntity.getVehicle();
+
+                if (vehicle != null) {
+                    bukkitEntity.leaveVehicle();
+                }
+
                 if (loc != null) {
-                    NMSHandler.entityHelper.faceLocation(entity.getBukkitEntity(), loc);
+                    NMSHandler.entityHelper.faceLocation(bukkitEntity, loc);
                 }
-                else {
-                    if (entity.isPlayer()) {
-                        Location playerTeleDest = entity.getLocation().clone();
-                        float relYaw = (yawRaw - playerTeleDest.getYaw()) % 360;
-                        if (relYaw > 180) {
-                            relYaw -= 360;
-                        }
-                        final float actualRelYaw = relYaw;
-                        float relPitch = pitchRaw - playerTeleDest.getPitch();
-                        playerTeleDest.setYaw(yawRaw);
-                        playerTeleDest.setPitch(pitchRaw);
-                        Player player = entity.getPlayer();
+                else if (entity.isPlayer()) {
+                    Location playerTeleDest = entity.getLocation().clone();
+                    float relYaw = (yawRaw - playerTeleDest.getYaw()) % 360;
+                    if (relYaw > 180) {
+                        relYaw -= 360;
+                    }
+                    final float actualRelYaw = relYaw;
+                    float relPitch = pitchRaw - playerTeleDest.getPitch();
+                    playerTeleDest.setYaw(yawRaw);
+                    playerTeleDest.setPitch(pitchRaw);
+                    Player player = entity.getPlayer();
+
+                    if (vehicle != null) {
+                        PaperAPITools.instance.teleport(player, playerTeleDest, PlayerTeleportEvent.TeleportCause.PLUGIN, null, Arrays.asList(TeleportCommand.Relative.values()));
+                    }
+                    else {
+                        final int times = offthreadRepeats != null ? offthreadRepeats.asInt() : 0;
+                        final float stepYaw = times > 0 ? actualRelYaw / (times + 1) : actualRelYaw;
+                        final float stepPitch = times > 0 ? relPitch / (times + 1) : relPitch;
+
                         if (NMSHandler.getVersion().isAtLeast(NMSVersion.v1_19)) {
                             NetworkInterceptHelper.enable();
-                            NMSHandler.packetHelper.sendRelativeLookPacket(player, actualRelYaw, relPitch);
+                            NMSHandler.packetHelper.sendRelativeLookPacket(player, stepYaw, stepPitch);
                         }
                         else {
                             PaperAPITools.instance.teleport(player, playerTeleDest, PlayerTeleportEvent.TeleportCause.PLUGIN, null, Arrays.asList(TeleportCommand.Relative.values()));
                         }
+
                         if (offthreadRepeats != null) {
                             NetworkInterceptHelper.enable();
-                            int times = offthreadRepeats.asInt();
                             int ms = 50 / (times + 1);
                             DenizenCore.runAsync(() -> {
                                 try {
                                     for (int i = 0; i < times; i++) {
                                         Thread.sleep(ms);
-                                        NMSHandler.packetHelper.sendRelativeLookPacket(player, actualRelYaw, relPitch);
+                                        NMSHandler.packetHelper.sendRelativeLookPacket(player, stepYaw, stepPitch);
                                     }
                                 }
                                 catch (Throwable ex) {
@@ -164,9 +182,31 @@ public static void autoExecute(ScriptEntry scriptEntry,
                             });
                         }
                     }
+                }
+                else {
+                    NMSHandler.entityHelper.rotate(bukkitEntity, yawRaw, pitchRaw);
+                }
+
+                if (vehicle != null) {
+                    Location vLoc = vehicle.getLocation().clone();
+                    if (loc != null) {
+                        Vector dir = loc.toVector().subtract(vLoc.toVector());
+                        if (dir.lengthSquared() > 0) {
+                            vLoc.setDirection(dir);
+                        }
+                    }
                     else {
-                        NMSHandler.entityHelper.rotate(entity.getBukkitEntity(), yawRaw, pitchRaw);
+                        vLoc.setYaw(yawRaw);
+                        vLoc.setPitch(pitchRaw);
                     }
+                    
+                    vehicle.teleport(vLoc, PlayerTeleportEvent.TeleportCause.PLUGIN);
+
+                    Bukkit.getScheduler().runTask(Denizen.getInstance(), () -> {
+                        if (vehicle.isValid() && bukkitEntity.isValid()) {
+                            vehicle.addPassenger(bukkitEntity);
+                        }
+                    });
                 }
             }
         }
@@ -174,6 +214,7 @@ public static void autoExecute(ScriptEntry scriptEntry,
             for (EntityTag entity : entities) {
                 BukkitRunnable task = new BukkitRunnable() {
                     long bounces = 0;
+
                     public void run() {
                         bounces++;
                         if (bounces > duration.getTicks()) {
@@ -182,11 +223,20 @@ public void run() {
                             return;
                         }
                         if (entity.isSpawned()) {
+                            Entity target = entity.getBukkitEntity();
+                            Entity vehicle = target.getVehicle();
+
                             if (loc != null) {
-                                NMSHandler.entityHelper.faceLocation(entity.getBukkitEntity(), loc);
+                                NMSHandler.entityHelper.faceLocation(target, loc);
+                                if (vehicle != null) {
+                                    NMSHandler.entityHelper.faceLocation(vehicle, loc);
+                                }
                             }
                             else {
-                                NMSHandler.entityHelper.rotate(entity.getBukkitEntity(), yawRaw, pitchRaw);
+                                NMSHandler.entityHelper.rotate(target, yawRaw, pitchRaw);
+                                if (vehicle != null) {
+                                    NMSHandler.entityHelper.rotate(vehicle, yawRaw, pitchRaw);
+                                }
                             }
                         }
                     }
diff --git a/plugin/src/main/java/com/denizenscript/denizen/scripts/commands/entity/TeleportCommand.java b/plugin/src/main/java/com/denizenscript/denizen/scripts/commands/entity/TeleportCommand.java
index 616b2cc591..3d8077f847 100644
--- a/plugin/src/main/java/com/denizenscript/denizen/scripts/commands/entity/TeleportCommand.java
+++ b/plugin/src/main/java/com/denizenscript/denizen/scripts/commands/entity/TeleportCommand.java
@@ -1,5 +1,6 @@
 package com.denizenscript.denizen.scripts.commands.entity;
 
+import com.denizenscript.denizen.Denizen;
 import com.denizenscript.denizen.nms.NMSHandler;
 import com.denizenscript.denizen.objects.EntityTag;
 import com.denizenscript.denizen.objects.LocationTag;
@@ -19,6 +20,8 @@
 import com.denizenscript.denizencore.utilities.Deprecations;
 import com.denizenscript.denizencore.utilities.debugging.Debug;
 import net.citizensnpcs.trait.CurrentLocation;
+import org.bukkit.Bukkit;
+import org.bukkit.entity.Entity;
 import org.bukkit.entity.Player;
 import org.bukkit.event.player.PlayerTeleportEvent;
 import org.bukkit.util.Vector;
@@ -153,9 +156,23 @@ else if (entityList.identify().startsWith("l@")) { // Compensate for legacy enti
                 Debug.echoError("Cannot interpret object '" + entityObj + "' as an EntityTag.");
                 continue;
             }
+            Entity bukkitEntity = entity.getBukkitEntity();
+            Entity vehicle = bukkitEntity.getVehicle();
+            if (vehicle != null) {
+                bukkitEntity.leaveVehicle();
+            }
+
             if (entity.isFake && entity.getWorld().equals(location.getWorld())) {
-                NMSHandler.entityHelper.snapPositionTo(entity.getBukkitEntity(), location.toVector());
-                NMSHandler.entityHelper.look(entity.getBukkitEntity(), location.getYaw(), location.getPitch());
+                NMSHandler.entityHelper.snapPositionTo(bukkitEntity, location.toVector());
+                NMSHandler.entityHelper.look(bukkitEntity, location.getYaw(), location.getPitch());
+                if (vehicle != null) {
+                    vehicle.teleport(location, cause);
+                    Bukkit.getScheduler().runTask(Denizen.getInstance(), () -> {
+                        if (vehicle.isValid() && bukkitEntity.isValid()) {
+                            vehicle.addPassenger(bukkitEntity);
+                        }
+                    });
+                }
                 return;
             }
             if (offthreadRepeats != null && relativeAxes != null && entity.isPlayer()) {
@@ -187,6 +204,16 @@ else if (entityList.identify().startsWith("l@")) { // Compensate for legacy enti
                 }
                 List<Relative> finalRelativeAxes = relativeAxes;
                 NMSHandler.packetHelper.sendRelativePositionPacket(player, x, y, z, yaw, pitch, finalRelativeAxes);
+
+                if (vehicle != null) {
+                    vehicle.teleport(location, cause);
+                    Bukkit.getScheduler().runTask(Denizen.getInstance(), () -> {
+                        if (vehicle.isValid() && bukkitEntity.isValid()) {
+                            vehicle.addPassenger(bukkitEntity);
+                        }
+                    });
+                }
+
                 DenizenCore.runAsync(() -> {
                     try {
                         for (int i = 0; i < times - 1; i++) {
@@ -201,10 +228,20 @@ else if (entityList.identify().startsWith("l@")) { // Compensate for legacy enti
                 continue;
             }
             if (entityOptions != null || relativeAxes != null) {
-                PaperAPITools.instance.teleport(entity.getBukkitEntity(), location, cause, entityOptions, relativeAxes);
-                continue;
+                PaperAPITools.instance.teleport(bukkitEntity, location, cause, entityOptions, relativeAxes);
+            }
+            else {
+                entity.teleport(location, cause);
+            }
+
+            if (vehicle != null) {
+                vehicle.teleport(location, cause);
+                Bukkit.getScheduler().runTask(Denizen.getInstance(), () -> {
+                    if (vehicle.isValid() && bukkitEntity.isValid()) {
+                        vehicle.addPassenger(bukkitEntity);
+                    }
+                });
             }
-            entity.teleport(location, cause);
         }
     }
 }