diff --git a/src/main/java/com/onarandombox/MultiverseCore/config/MVCoreConfigNodes.java b/src/main/java/com/onarandombox/MultiverseCore/config/MVCoreConfigNodes.java
index 4aa05878..36632653 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/config/MVCoreConfigNodes.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/config/MVCoreConfigNodes.java
@@ -6,7 +6,9 @@ import com.onarandombox.MultiverseCore.configuration.node.ConfigNode;
 import com.onarandombox.MultiverseCore.configuration.node.Node;
 import com.onarandombox.MultiverseCore.configuration.node.NodeGroup;
 import com.onarandombox.MultiverseCore.event.MVDebugModeEvent;
+import com.onarandombox.MultiverseCore.exceptions.MultiverseException;
 import io.github.townyadvanced.commentedconfiguration.setting.CommentedNode;
+import io.vavr.control.Try;
 import org.bukkit.plugin.PluginManager;
 
 class MVCoreConfigNodes {
@@ -128,7 +130,9 @@ class MVCoreConfigNodes {
             .comment("This only applies if use-custom-portal-search is set to true.")
             .defaultValue(128)
             .name("custom-portal-search-radius")
-            .validator(value -> value >= 0)
+            .validator(value -> value < 0
+                    ? Try.failure(new MultiverseException("The value must be greater than or equal to 0.", null))
+                    : Try.success(null))
             .build());
 
     private final ConfigHeaderNode MESSAGING_HEADER = node(ConfigHeaderNode.builder("messaging")
@@ -174,7 +178,9 @@ class MVCoreConfigNodes {
             .comment("  3 = finest")
             .defaultValue(0)
             .name("global-debug")
-            .validator(value -> value >= 0 && value <= 3)
+            .validator(value -> (value < 0 || value > 3)
+                    ? Try.failure(new MultiverseException("Debug level must be between 0 and 3.", null))
+                    : Try.success(null))
             .onSetValue((oldValue, newValue) -> {
                 int level = Logging.getDebugLevel();
                 Logging.setDebugLevel(newValue);
diff --git a/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/FileConfigHandle.java b/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/FileConfigHandle.java
index f5742fb5..aa74e57c 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/FileConfigHandle.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/FileConfigHandle.java
@@ -165,13 +165,12 @@ abstract class FileConfigHandle<C extends FileConfiguration> {
      * @param <T>   The type of the node value.
      */
     public <T> Try<Void> set(@NotNull ValueNode<T> node, T value) {
-        if (!node.validate(value)) {
-            return Try.failure(new MultiverseException("Validation failed", null)); // TODO replace validation
-        }
-        T oldValue = get(node);
-        config.set(node.getPath(), value);
-        node.onSetValue(oldValue, get(node));
-        return Try.success(null);
+        return node.validate(value).map(ignore -> {
+            T oldValue = get(node);
+            config.set(node.getPath(), value);
+            node.onSetValue(oldValue, get(node));
+            return null;
+        });
     }
 
     /**
diff --git a/src/main/java/com/onarandombox/MultiverseCore/configuration/node/ConfigNode.java b/src/main/java/com/onarandombox/MultiverseCore/configuration/node/ConfigNode.java
index 42d3f12f..d575b7e5 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/configuration/node/ConfigNode.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/configuration/node/ConfigNode.java
@@ -4,6 +4,7 @@ import java.util.function.BiConsumer;
 import java.util.function.Function;
 
 import io.vavr.control.Option;
+import io.vavr.control.Try;
 import org.jetbrains.annotations.NotNull;
 import org.jetbrains.annotations.Nullable;
 
@@ -31,7 +32,7 @@ public class ConfigNode<T> extends ConfigHeaderNode implements ValueNode<T> {
     protected final @Nullable String name;
     protected final @NotNull Class<T> type;
     protected final @Nullable T defaultValue;
-    protected final @Nullable Function<T, Boolean> validator;
+    protected final @Nullable Function<T, Try<Void>> validator;
     protected final @Nullable BiConsumer<T, T> onSetValue;
 
     protected ConfigNode(
@@ -40,7 +41,7 @@ public class ConfigNode<T> extends ConfigHeaderNode implements ValueNode<T> {
             @Nullable String name,
             @NotNull Class<T> type,
             @Nullable T defaultValue,
-            @Nullable Function<T, Boolean> validator,
+            @Nullable Function<T, Try<Void>> validator,
             @Nullable BiConsumer<T, T> onSetValue
     ) {
         super(path, comments);
@@ -79,11 +80,11 @@ public class ConfigNode<T> extends ConfigHeaderNode implements ValueNode<T> {
      * {@inheritDoc}
      */
     @Override
-    public boolean validate(@Nullable T value) {
+    public Try<Void> validate(@Nullable T value) {
         if (validator != null) {
             return validator.apply(value);
         }
-        return true;
+        return Try.success(null);
     }
 
     /**
@@ -107,7 +108,7 @@ public class ConfigNode<T> extends ConfigHeaderNode implements ValueNode<T> {
         protected @Nullable String name;
         protected @NotNull final Class<T> type;
         protected @Nullable T defaultValue;
-        protected @Nullable Function<T, Boolean> validator;
+        protected @Nullable Function<T, Try<Void>> validator;
         protected @Nullable BiConsumer<T, T> onSetValue;
 
         /**
@@ -144,7 +145,7 @@ public class ConfigNode<T> extends ConfigHeaderNode implements ValueNode<T> {
             return (B) this;
         }
 
-        public @NotNull B validator(@NotNull Function<T, Boolean> validator) {
+        public @NotNull B validator(@NotNull Function<T, Try<Void>> validator) {
             this.validator = validator;
             return (B) this;
         }
diff --git a/src/main/java/com/onarandombox/MultiverseCore/configuration/node/ValueNode.java b/src/main/java/com/onarandombox/MultiverseCore/configuration/node/ValueNode.java
index 6ef0cf81..9aebfae5 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/configuration/node/ValueNode.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/configuration/node/ValueNode.java
@@ -1,6 +1,7 @@
 package com.onarandombox.MultiverseCore.configuration.node;
 
 import io.vavr.control.Option;
+import io.vavr.control.Try;
 import org.jetbrains.annotations.NotNull;
 import org.jetbrains.annotations.Nullable;
 
@@ -33,7 +34,7 @@ public interface ValueNode<T> extends Node {
      * @param value The value to validate.
      * @return True if the value is valid, false otherwise.
      */
-    boolean validate(@Nullable T value);
+    Try<Void> validate(@Nullable T value);
 
     /**
      * Called when the value of this node is set.