diff --git a/worldedit-bukkit/adapters/adapter-1.21.11/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_11/PaperweightAdapter.java b/worldedit-bukkit/adapters/adapter-1.21.11/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_11/PaperweightAdapter.java
index 338da89d62..51ae63749b 100644
--- a/worldedit-bukkit/adapters/adapter-1.21.11/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_11/PaperweightAdapter.java
+++ b/worldedit-bukkit/adapters/adapter-1.21.11/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_11/PaperweightAdapter.java
@@ -70,6 +70,7 @@
 import com.sk89q.worldedit.world.generation.ConfiguredFeatureType;
 import com.sk89q.worldedit.world.generation.StructureType;
 import com.sk89q.worldedit.world.generation.TreeType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeTypes;
 import com.sk89q.worldedit.world.item.ItemType;
 import com.sk89q.worldedit.world.registry.BlockMaterial;
 import net.minecraft.SharedConstants;
@@ -978,6 +979,7 @@ public void initializeRegistries() {
                 }
             }
         }
+        WorldEditTreeTypes.init();
 
         // BiomeCategories
         Registry<Biome> biomeRegistry = server.registryAccess().lookupOrThrow(Registries.BIOME);
diff --git a/worldedit-bukkit/adapters/adapter-1.21.4/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_4/PaperweightAdapter.java b/worldedit-bukkit/adapters/adapter-1.21.4/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_4/PaperweightAdapter.java
index 70f0d3065b..4a80baa1d7 100644
--- a/worldedit-bukkit/adapters/adapter-1.21.4/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_4/PaperweightAdapter.java
+++ b/worldedit-bukkit/adapters/adapter-1.21.4/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_4/PaperweightAdapter.java
@@ -70,6 +70,7 @@
 import com.sk89q.worldedit.world.generation.ConfiguredFeatureType;
 import com.sk89q.worldedit.world.generation.StructureType;
 import com.sk89q.worldedit.world.generation.TreeType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeTypes;
 import com.sk89q.worldedit.world.item.ItemType;
 import com.sk89q.worldedit.world.registry.BlockMaterial;
 import net.minecraft.SharedConstants;
@@ -942,6 +943,7 @@ public void initializeRegistries() {
                 }
             }
         }
+        WorldEditTreeTypes.init();
 
         // BiomeCategories
         Registry<Biome> biomeRegistry = server.registryAccess().lookupOrThrow(Registries.BIOME);
diff --git a/worldedit-bukkit/adapters/adapter-1.21.5/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_5/PaperweightAdapter.java b/worldedit-bukkit/adapters/adapter-1.21.5/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_5/PaperweightAdapter.java
index 35f34eb930..ff1a2c2486 100644
--- a/worldedit-bukkit/adapters/adapter-1.21.5/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_5/PaperweightAdapter.java
+++ b/worldedit-bukkit/adapters/adapter-1.21.5/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_5/PaperweightAdapter.java
@@ -70,6 +70,7 @@
 import com.sk89q.worldedit.world.generation.ConfiguredFeatureType;
 import com.sk89q.worldedit.world.generation.StructureType;
 import com.sk89q.worldedit.world.generation.TreeType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeTypes;
 import com.sk89q.worldedit.world.item.ItemType;
 import com.sk89q.worldedit.world.registry.BlockMaterial;
 import net.minecraft.SharedConstants;
@@ -940,6 +941,7 @@ public void initializeRegistries() {
                 }
             }
         }
+        WorldEditTreeTypes.init();
 
         // BiomeCategories
         Registry<Biome> biomeRegistry = server.registryAccess().lookupOrThrow(Registries.BIOME);
diff --git a/worldedit-bukkit/adapters/adapter-1.21.6/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_6/PaperweightAdapter.java b/worldedit-bukkit/adapters/adapter-1.21.6/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_6/PaperweightAdapter.java
index 78345b9e07..40180c1e1a 100644
--- a/worldedit-bukkit/adapters/adapter-1.21.6/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_6/PaperweightAdapter.java
+++ b/worldedit-bukkit/adapters/adapter-1.21.6/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_6/PaperweightAdapter.java
@@ -70,6 +70,7 @@
 import com.sk89q.worldedit.world.generation.ConfiguredFeatureType;
 import com.sk89q.worldedit.world.generation.StructureType;
 import com.sk89q.worldedit.world.generation.TreeType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeTypes;
 import com.sk89q.worldedit.world.item.ItemType;
 import com.sk89q.worldedit.world.registry.BlockMaterial;
 import net.minecraft.SharedConstants;
@@ -977,6 +978,7 @@ public void initializeRegistries() {
                 }
             }
         }
+        WorldEditTreeTypes.init();
 
         // BiomeCategories
         Registry<Biome> biomeRegistry = server.registryAccess().lookupOrThrow(Registries.BIOME);
diff --git a/worldedit-bukkit/adapters/adapter-1.21.9/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_9/PaperweightAdapter.java b/worldedit-bukkit/adapters/adapter-1.21.9/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_9/PaperweightAdapter.java
index a8745f4504..43bc74789b 100644
--- a/worldedit-bukkit/adapters/adapter-1.21.9/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_9/PaperweightAdapter.java
+++ b/worldedit-bukkit/adapters/adapter-1.21.9/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v1_21_9/PaperweightAdapter.java
@@ -70,6 +70,7 @@
 import com.sk89q.worldedit.world.generation.ConfiguredFeatureType;
 import com.sk89q.worldedit.world.generation.StructureType;
 import com.sk89q.worldedit.world.generation.TreeType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeTypes;
 import com.sk89q.worldedit.world.item.ItemType;
 import com.sk89q.worldedit.world.registry.BlockMaterial;
 import net.minecraft.SharedConstants;
@@ -975,6 +976,7 @@ public void initializeRegistries() {
                 }
             }
         }
+        WorldEditTreeTypes.init();
 
         // BiomeCategories
         Registry<Biome> biomeRegistry = server.registryAccess().lookupOrThrow(Registries.BIOME);
diff --git a/worldedit-bukkit/adapters/adapter-26.1/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v26_1/PaperweightAdapter.java b/worldedit-bukkit/adapters/adapter-26.1/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v26_1/PaperweightAdapter.java
index 59a24f0243..8c39281947 100644
--- a/worldedit-bukkit/adapters/adapter-26.1/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v26_1/PaperweightAdapter.java
+++ b/worldedit-bukkit/adapters/adapter-26.1/src/main/java/com/sk89q/worldedit/bukkit/adapter/impl/v26_1/PaperweightAdapter.java
@@ -69,6 +69,7 @@
 import com.sk89q.worldedit.world.generation.ConfiguredFeatureType;
 import com.sk89q.worldedit.world.generation.StructureType;
 import com.sk89q.worldedit.world.generation.TreeType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeTypes;
 import com.sk89q.worldedit.world.item.ItemType;
 import com.sk89q.worldedit.world.registry.BlockMaterial;
 import io.papermc.paper.world.PaperWorldLoader;
@@ -967,6 +968,7 @@ public void initializeRegistries() {
                 }
             }
         }
+        WorldEditTreeTypes.init();
 
         // BiomeCategories
         Registry<Biome> biomeRegistry = server.registryAccess().lookupOrThrow(Registries.BIOME);
diff --git a/worldedit-bukkit/src/main/java/com/sk89q/worldedit/bukkit/BukkitWorld.java b/worldedit-bukkit/src/main/java/com/sk89q/worldedit/bukkit/BukkitWorld.java
index 024a782270..664023ccbe 100644
--- a/worldedit-bukkit/src/main/java/com/sk89q/worldedit/bukkit/BukkitWorld.java
+++ b/worldedit-bukkit/src/main/java/com/sk89q/worldedit/bukkit/BukkitWorld.java
@@ -50,6 +50,7 @@
 import com.sk89q.worldedit.world.block.BlockStateHolder;
 import com.sk89q.worldedit.world.generation.ConfiguredFeatureType;
 import com.sk89q.worldedit.world.generation.StructureType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeGeneration;
 import com.sk89q.worldedit.world.weather.WeatherType;
 import com.sk89q.worldedit.world.weather.WeatherTypes;
 import io.papermc.lib.PaperLib;
@@ -318,6 +319,10 @@ public boolean generateTree(TreeGenerator.TreeType type, EditSession editSession
 
     @Override
     public boolean generateTree(com.sk89q.worldedit.world.generation.TreeType type, EditSession editSession, BlockVector3 position) throws MaxChangedBlocksException {
+        Boolean customResult = WorldEditTreeGeneration.handleWorldEditTrees(this, type, editSession, position);
+        if (customResult != null) {
+            return customResult;
+        }
         BukkitImplAdapter adapter = WorldEditPlugin.getInstance().getBukkitImplAdapter();
         if (adapter != null) {
             return adapter.generateTree(type, getWorld(), editSession, position);
diff --git a/worldedit-core/src/main/java/com/sk89q/worldedit/world/generation/WorldEditTreeGeneration.java b/worldedit-core/src/main/java/com/sk89q/worldedit/world/generation/WorldEditTreeGeneration.java
new file mode 100644
index 0000000000..483d910337
--- /dev/null
+++ b/worldedit-core/src/main/java/com/sk89q/worldedit/world/generation/WorldEditTreeGeneration.java
@@ -0,0 +1,55 @@
+/*
+ * WorldEdit, a Minecraft world manipulation toolkit
+ * Copyright (C) sk89q <http://www.sk89q.com>
+ * Copyright (C) WorldEdit team and contributors
+ *
+ * This program is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU General Public License as published by
+ * the Free Software Foundation, either version 3 of the License, or
+ * (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU General Public License for more details.
+ *
+ * You should have received a copy of the GNU General Public License
+ * along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+package com.sk89q.worldedit.world.generation;
+
+import com.google.common.collect.Iterables;
+import com.sk89q.worldedit.EditSession;
+import com.sk89q.worldedit.MaxChangedBlocksException;
+import com.sk89q.worldedit.math.BlockVector3;
+import com.sk89q.worldedit.world.World;
+
+import java.util.Collection;
+import java.util.concurrent.ThreadLocalRandom;
+import javax.annotation.Nullable;
+
+public final class WorldEditTreeGeneration {
+
+    private WorldEditTreeGeneration() {
+    }
+
+    @SuppressWarnings("deprecation")
+    @Nullable
+    public static Boolean handleWorldEditTrees(World world, TreeType type, EditSession editSession, BlockVector3 position)
+            throws MaxChangedBlocksException {
+        if (type == WorldEditTreeTypes.RANDOM) {
+            Collection<TreeType> treeTypes = TreeType.REGISTRY.values();
+            TreeType randomType = Iterables.get(treeTypes, ThreadLocalRandom.current().nextInt(treeTypes.size()));
+            return world.generateTree(randomType, editSession, position);
+        }
+
+        if (type == WorldEditTreeTypes.PINE) {
+            // TODO Move this into this file once the legacy system is stripped away
+            return com.sk89q.worldedit.util.TreeGenerator.TreeType.PINE.generate(editSession, position);
+        }
+
+        return null;
+    }
+
+}
diff --git a/worldedit-core/src/main/java/com/sk89q/worldedit/world/generation/WorldEditTreeTypes.java b/worldedit-core/src/main/java/com/sk89q/worldedit/world/generation/WorldEditTreeTypes.java
new file mode 100644
index 0000000000..834fc70008
--- /dev/null
+++ b/worldedit-core/src/main/java/com/sk89q/worldedit/world/generation/WorldEditTreeTypes.java
@@ -0,0 +1,47 @@
+/*
+ * WorldEdit, a Minecraft world manipulation toolkit
+ * Copyright (C) sk89q <http://www.sk89q.com>
+ * Copyright (C) WorldEdit team and contributors
+ *
+ * This program is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU General Public License as published by
+ * the Free Software Foundation, either version 3 of the License, or
+ * (at your option) any later version.
+ *
+ * This program is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU General Public License for more details.
+ *
+ * You should have received a copy of the GNU General Public License
+ * along with this program.  If not, see <https://www.gnu.org/licenses/>.
+ */
+
+package com.sk89q.worldedit.world.generation;
+
+/**
+ * This class holds custom trees added by WorldEdit.
+ */
+public final class WorldEditTreeTypes {
+
+    public static final TreeType RANDOM = create("random");
+    public static final TreeType PINE = create("pine");
+
+    private WorldEditTreeTypes() {
+    }
+
+    public static void init() {
+        register(RANDOM);
+        register(PINE);
+    }
+
+    private static TreeType create(String id) {
+        return new TreeType("worldedit:" + id);
+    }
+
+    private static void register(TreeType type) {
+        if (TreeType.REGISTRY.get(type.id()) == null) {
+            TreeType.REGISTRY.register(type.id(), type);
+        }
+    }
+}
diff --git a/worldedit-fabric/src/main/java/com/sk89q/worldedit/fabric/FabricWorld.java b/worldedit-fabric/src/main/java/com/sk89q/worldedit/fabric/FabricWorld.java
index 891955dbfc..bb81378a7c 100644
--- a/worldedit-fabric/src/main/java/com/sk89q/worldedit/fabric/FabricWorld.java
+++ b/worldedit-fabric/src/main/java/com/sk89q/worldedit/fabric/FabricWorld.java
@@ -64,6 +64,7 @@
 import com.sk89q.worldedit.world.generation.ConfiguredFeatureType;
 import com.sk89q.worldedit.world.generation.StructureType;
 import com.sk89q.worldedit.world.generation.TreeType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeGeneration;
 import com.sk89q.worldedit.world.item.ItemTypes;
 import com.sk89q.worldedit.world.weather.WeatherType;
 import com.sk89q.worldedit.world.weather.WeatherTypes;
@@ -486,6 +487,10 @@ public boolean generateTree(com.sk89q.worldedit.util.TreeGenerator.TreeType type
 
     @Override
     public boolean generateTree(TreeType type, EditSession editSession, BlockVector3 position) throws MaxChangedBlocksException {
+        Boolean customResult = WorldEditTreeGeneration.handleWorldEditTrees(this, type, editSession, position);
+        if (customResult != null) {
+            return customResult;
+        }
         ServerLevel world = (ServerLevel) getWorld();
         PlacedFeature generator = world.registryAccess().lookupOrThrow(Registries.PLACED_FEATURE).getValue(Identifier.tryParse(type.id()));
         ServerChunkCache chunkManager = world.getChunkSource();
diff --git a/worldedit-fabric/src/main/java/com/sk89q/worldedit/fabric/FabricWorldEdit.java b/worldedit-fabric/src/main/java/com/sk89q/worldedit/fabric/FabricWorldEdit.java
index 8146e32e75..6ba2f6c410 100644
--- a/worldedit-fabric/src/main/java/com/sk89q/worldedit/fabric/FabricWorldEdit.java
+++ b/worldedit-fabric/src/main/java/com/sk89q/worldedit/fabric/FabricWorldEdit.java
@@ -46,6 +46,7 @@
 import com.sk89q.worldedit.world.generation.ConfiguredFeatureType;
 import com.sk89q.worldedit.world.generation.StructureType;
 import com.sk89q.worldedit.world.generation.TreeType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeTypes;
 import com.sk89q.worldedit.world.item.ItemCategory;
 import com.sk89q.worldedit.world.item.ItemType;
 import com.sk89q.worldedit.world.weather.WeatherTypes;
@@ -319,6 +320,7 @@ private void setupRegistries(MinecraftServer server) {
                 }
             }
         }
+        WorldEditTreeTypes.init();
 
         // ... :|
         GameModes.get("");
diff --git a/worldedit-neoforge/src/main/java/com/sk89q/worldedit/neoforge/NeoForgeWorld.java b/worldedit-neoforge/src/main/java/com/sk89q/worldedit/neoforge/NeoForgeWorld.java
index c5d1cefff8..b59c68be4d 100644
--- a/worldedit-neoforge/src/main/java/com/sk89q/worldedit/neoforge/NeoForgeWorld.java
+++ b/worldedit-neoforge/src/main/java/com/sk89q/worldedit/neoforge/NeoForgeWorld.java
@@ -62,6 +62,7 @@
 import com.sk89q.worldedit.world.block.BlockStateHolder;
 import com.sk89q.worldedit.world.generation.ConfiguredFeatureType;
 import com.sk89q.worldedit.world.generation.StructureType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeGeneration;
 import com.sk89q.worldedit.world.item.ItemTypes;
 import com.sk89q.worldedit.world.weather.WeatherType;
 import com.sk89q.worldedit.world.weather.WeatherTypes;
@@ -474,6 +475,10 @@ public boolean generateTree(com.sk89q.worldedit.util.TreeGenerator.TreeType type
 
     @Override
     public boolean generateTree(com.sk89q.worldedit.world.generation.TreeType type, EditSession editSession, BlockVector3 position) throws MaxChangedBlocksException {
+        Boolean customResult = WorldEditTreeGeneration.handleWorldEditTrees(this, type, editSession, position);
+        if (customResult != null) {
+            return customResult;
+        }
         ServerLevel world = getWorld();
         PlacedFeature generator = world.registryAccess().lookupOrThrow(Registries.PLACED_FEATURE).getValue(Identifier.tryParse(type.id()));
         ServerChunkCache chunkManager = world.getChunkSource();
diff --git a/worldedit-neoforge/src/main/java/com/sk89q/worldedit/neoforge/NeoForgeWorldEdit.java b/worldedit-neoforge/src/main/java/com/sk89q/worldedit/neoforge/NeoForgeWorldEdit.java
index 87cbda4a76..d16a89fd60 100644
--- a/worldedit-neoforge/src/main/java/com/sk89q/worldedit/neoforge/NeoForgeWorldEdit.java
+++ b/worldedit-neoforge/src/main/java/com/sk89q/worldedit/neoforge/NeoForgeWorldEdit.java
@@ -46,6 +46,7 @@
 import com.sk89q.worldedit.world.generation.ConfiguredFeatureType;
 import com.sk89q.worldedit.world.generation.StructureType;
 import com.sk89q.worldedit.world.generation.TreeType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeTypes;
 import com.sk89q.worldedit.world.item.ItemCategory;
 import com.sk89q.worldedit.world.item.ItemType;
 import com.sk89q.worldedit.world.weather.WeatherTypes;
@@ -246,6 +247,7 @@ private void setupRegistries(MinecraftServer server) {
                 }
             }
         }
+        WorldEditTreeTypes.init();
 
         // ... :|
         GameModes.get("");
diff --git a/worldedit-sponge/src/main/java/com/sk89q/worldedit/sponge/SpongeWorld.java b/worldedit-sponge/src/main/java/com/sk89q/worldedit/sponge/SpongeWorld.java
index e82e9b98e9..a42bf69c5c 100644
--- a/worldedit-sponge/src/main/java/com/sk89q/worldedit/sponge/SpongeWorld.java
+++ b/worldedit-sponge/src/main/java/com/sk89q/worldedit/sponge/SpongeWorld.java
@@ -48,6 +48,7 @@
 import com.sk89q.worldedit.world.block.BlockState;
 import com.sk89q.worldedit.world.block.BlockStateHolder;
 import com.sk89q.worldedit.world.generation.TreeType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeGeneration;
 import com.sk89q.worldedit.world.item.ItemTypes;
 import com.sk89q.worldedit.world.weather.WeatherType;
 import com.sk89q.worldedit.world.weather.WeatherTypes;
@@ -381,6 +382,10 @@ public boolean generateTree(TreeGenerator.TreeType type, EditSession editSession
 
     @Override
     public boolean generateTree(TreeType type, EditSession editSession, BlockVector3 position) throws MaxChangedBlocksException {
+        Boolean customResult = WorldEditTreeGeneration.handleWorldEditTrees(this, type, editSession, position);
+        if (customResult != null) {
+            return customResult;
+        }
         ServerLevel world = (ServerLevel) getWorld();
         PlacedFeature generator = world.registryAccess().lookupOrThrow(Registries.PLACED_FEATURE).getValue(Identifier.tryParse(type.id()));
         return generator != null && generator.place(
diff --git a/worldedit-sponge/src/main/java/com/sk89q/worldedit/sponge/SpongeWorldEdit.java b/worldedit-sponge/src/main/java/com/sk89q/worldedit/sponge/SpongeWorldEdit.java
index 5cf5e4c893..eb38c91396 100644
--- a/worldedit-sponge/src/main/java/com/sk89q/worldedit/sponge/SpongeWorldEdit.java
+++ b/worldedit-sponge/src/main/java/com/sk89q/worldedit/sponge/SpongeWorldEdit.java
@@ -41,6 +41,7 @@
 import com.sk89q.worldedit.world.biome.BiomeType;
 import com.sk89q.worldedit.world.block.BlockCategory;
 import com.sk89q.worldedit.world.generation.TreeType;
+import com.sk89q.worldedit.world.generation.WorldEditTreeTypes;
 import com.sk89q.worldedit.world.item.ItemCategory;
 import net.kyori.adventure.audience.Audience;
 import org.apache.logging.log4j.Logger;
@@ -223,6 +224,7 @@ public void serverStarted(StartedEngineEvent<Server> event) {
                 }
             }
         });
+        WorldEditTreeTypes.init();
         event.game().registry(RegistryTypes.BLOCK_TYPE).tags().forEach(blockTypeTag -> {
             String id = blockTypeTag.key().asString();
             if (!BlockCategory.REGISTRY.keySet().contains(id)) {