diff --git a/src/main/java/com/onarandombox/MultiverseCore/MultiverseCore.java b/src/main/java/com/onarandombox/MultiverseCore/MultiverseCore.java
index d69f316e..2d6f0899 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/MultiverseCore.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/MultiverseCore.java
@@ -358,7 +358,8 @@ public class MultiverseCore extends JavaPlugin implements MVCore {
      */
     @Override
     public boolean saveAllConfigs() {
-        return configProvider.get().save()
+        // TODO: Make this all Try<Void>
+        return configProvider.get().save().isSuccess()
                 && worldManagerProvider.get().saveWorldsConfig()
                 && anchorManagerProvider.get().saveAnchors();
     }
diff --git a/src/main/java/com/onarandombox/MultiverseCore/api/MVConfig.java b/src/main/java/com/onarandombox/MultiverseCore/api/MVConfig.java
index 55d11a78..c852a627 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/api/MVConfig.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/api/MVConfig.java
@@ -12,7 +12,7 @@ public interface MVConfig {
      * Loads the config from disk.
      * @return True if the config was loaded successfully.
      */
-    boolean load();
+    Try<Void> load();
 
     /**
      * Whether the config has been loaded.
@@ -23,7 +23,7 @@ public interface MVConfig {
     /**
      * Saves the config to disk.
      */
-    boolean save();
+    Try<Void> save();
 
     /**
      * Gets the nodes for the config.
diff --git a/src/main/java/com/onarandombox/MultiverseCore/commands/ReloadCommand.java b/src/main/java/com/onarandombox/MultiverseCore/commands/ReloadCommand.java
index ee269b44..dcee3cd1 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/commands/ReloadCommand.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/commands/ReloadCommand.java
@@ -50,7 +50,8 @@ public class ReloadCommand extends MultiverseCommand {
     public void onReloadCommand(@NotNull BukkitCommandIssuer issuer) {
         issuer.sendInfo(MVCorei18n.RELOAD_RELOADING);
         try {
-            this.config.load();
+            // TODO: Make this all Try<Void>
+            this.config.load().getOrElseThrow(e -> new RuntimeException("Failed to load config", e));
             this.worldManager.initAllWorlds();
             this.anchorManager.loadAnchors();
         } catch (Exception e) {
diff --git a/src/main/java/com/onarandombox/MultiverseCore/config/MVCoreConfig.java b/src/main/java/com/onarandombox/MultiverseCore/config/MVCoreConfig.java
index 8afb8a18..1e713b84 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/config/MVCoreConfig.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/config/MVCoreConfig.java
@@ -89,7 +89,7 @@ public class MVCoreConfig implements MVConfig {
     }
 
     @Override
-    public boolean load() {
+    public Try<Void> load() {
         migrateFromOldConfigFile();
         return configHandle.load();
     }
@@ -100,9 +100,8 @@ public class MVCoreConfig implements MVConfig {
     }
 
     @Override
-    public boolean save() {
-        configHandle.save();
-        return true;
+    public Try<Void> save() {
+        return configHandle.save();
     }
 
     @Override
diff --git a/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/CommentedYamlConfigHandle.java b/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/CommentedYamlConfigHandle.java
index f43a2a86..b455fa47 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/CommentedYamlConfigHandle.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/CommentedYamlConfigHandle.java
@@ -1,5 +1,6 @@
 package com.onarandombox.MultiverseCore.configuration.handle;
 
+import java.io.IOException;
 import java.nio.file.Path;
 import java.util.logging.Logger;
 
@@ -9,6 +10,7 @@ import com.onarandombox.MultiverseCore.configuration.node.NodeGroup;
 import com.onarandombox.MultiverseCore.configuration.node.CommentedNode;
 import com.onarandombox.MultiverseCore.configuration.node.ValueNode;
 import io.github.townyadvanced.commentedconfiguration.CommentedConfiguration;
+import io.vavr.control.Try;
 import org.jetbrains.annotations.NotNull;
 import org.jetbrains.annotations.Nullable;
 
@@ -35,9 +37,12 @@ public class CommentedYamlConfigHandle extends FileConfigHandle<CommentedConfigu
      * {@inheritDoc}
      */
     @Override
-    protected boolean loadConfigObject() {
+    protected void loadConfigObject() throws IOException {
         config = new CommentedConfiguration(configPath, logger);
-        return config.load();
+        if (!config.load()) {
+            throw new IOException("Failed to load commented config file " + configPath
+                    + ". See console for details.");
+        }
     }
 
     /**
@@ -71,9 +76,9 @@ public class CommentedYamlConfigHandle extends FileConfigHandle<CommentedConfigu
      * {@inheritDoc}
      */
     @Override
-    public boolean save() {
-        config.save();
-        return true;
+    public Try<Void> save() {
+        // TODO: There is no way to check if the save was successful.
+        return Try.run(() -> config.save());
     }
 
     public static class Builder extends FileConfigHandle.Builder<CommentedConfiguration, Builder> {
diff --git a/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/ConfigurationSectionHandle.java b/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/ConfigurationSectionHandle.java
index 6802a166..6a3bf1b4 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/ConfigurationSectionHandle.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/ConfigurationSectionHandle.java
@@ -2,6 +2,7 @@ package com.onarandombox.MultiverseCore.configuration.handle;
 
 import com.onarandombox.MultiverseCore.configuration.migration.ConfigMigrator;
 import com.onarandombox.MultiverseCore.configuration.node.NodeGroup;
+import io.vavr.control.Try;
 import org.bukkit.configuration.ConfigurationSection;
 import org.jetbrains.annotations.NotNull;
 import org.jetbrains.annotations.Nullable;
@@ -16,7 +17,7 @@ public class ConfigurationSectionHandle extends GenericConfigHandle<Configuratio
         return new Builder<>(configurationSection);
     }
 
-    public ConfigurationSectionHandle(@NotNull ConfigurationSection configurationSection,
+    protected ConfigurationSectionHandle(@NotNull ConfigurationSection configurationSection,
                                       @Nullable Logger logger,
                                       @Nullable NodeGroup nodes,
                                       @Nullable ConfigMigrator migrator) {
@@ -24,6 +25,17 @@ public class ConfigurationSectionHandle extends GenericConfigHandle<Configuratio
         this.config = configurationSection;
     }
 
+    /**
+     * Loads the configuration with a new configuration section.
+     *
+     * @param section  The configuration section.
+     * @return Whether the configuration was loaded or its given error.
+     */
+    public Try<Void> load(@NotNull ConfigurationSection section) {
+        this.config = section;
+        return load();
+    }
+
     /**
      * Builder for {@link ConfigurationSectionHandle}.
      *
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 fd0cefb0..82d30dd8 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/FileConfigHandle.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/FileConfigHandle.java
@@ -5,12 +5,11 @@ import java.io.IOException;
 import java.nio.file.Path;
 import java.util.logging.Logger;
 
-import com.dumptruckman.minecraft.util.Logging;
 import com.onarandombox.MultiverseCore.configuration.migration.ConfigMigrator;
 import com.onarandombox.MultiverseCore.configuration.node.NodeGroup;
+import io.vavr.control.Try;
+import org.bukkit.configuration.InvalidConfigurationException;
 import org.bukkit.configuration.file.FileConfiguration;
-import org.bukkit.configuration.file.YamlConfiguration;
-import org.bukkit.plugin.Plugin;
 import org.jetbrains.annotations.NotNull;
 import org.jetbrains.annotations.Nullable;
 
@@ -33,49 +32,43 @@ abstract class FileConfigHandle<C extends FileConfiguration> extends GenericConf
      * {@inheritDoc}
      */
     @Override
-    public boolean load() {
-        boolean newFileCreated;
-        try {
-            newFileCreated = createConfigFile();
-        } catch (IOException e) {
-            Logging.severe("Failed to create config file: %s", configFile.getName());
-            Logging.severe(e.getMessage());
-            return false;
-        }
-        if (!loadConfigObject()) {
-            Logging.severe("Failed to load config file: %s", configFile.getName());
-            return false;
-        }
-        if (!newFileCreated) {
-            migrateConfig();
-        }
-        setUpNodes();
-        return true;
+    public Try<Void> load() {
+        boolean isNewFile = !configFile.exists();
+        return createConfigFile()
+                .andThenTry(this::loadConfigObject)
+                .andThenTry(() -> {
+                    if (!isNewFile) {
+                        migrateConfig();
+                    }
+                    setUpNodes();
+                });
     }
 
     /**
-     * Create a new config file if file does not exist
+     * Create a new config file if file does not exist.
      *
-     * @return True if file exist or created successfully, otherwise false.
+     * @return Whether the file was created or its given error.
      */
-    protected boolean createConfigFile() throws IOException {
-        if (configFile.exists()) {
-            return false;
-        }
-        return configFile.createNewFile();
+    protected Try<Void> createConfigFile() {
+        return Try.run(() -> {
+            if (configFile.exists()) {
+                return;
+            }
+            if (!configFile.createNewFile()) {
+                throw new IOException("Failed to create config file: " + configFile.getName());
+            }
+        });
     }
 
     /**
      * Loads the configuration object.
-     *
-     * @return True if the configuration was loaded successfully, false otherwise.
      */
-    protected abstract boolean loadConfigObject();
+    protected abstract void loadConfigObject() throws IOException, InvalidConfigurationException;
 
     /**
      * Saves the configuration.
      */
-    public abstract boolean save();
+    public abstract Try<Void> save();
 
     /**
      * Checks if the configuration is loaded.
diff --git a/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/GenericConfigHandle.java b/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/GenericConfigHandle.java
index 1ba4c7f0..6644f4aa 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/GenericConfigHandle.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/GenericConfigHandle.java
@@ -3,9 +3,7 @@ package com.onarandombox.MultiverseCore.configuration.handle;
 import com.onarandombox.MultiverseCore.configuration.migration.ConfigMigrator;
 import com.onarandombox.MultiverseCore.configuration.node.ConfigNodeNotFoundException;
 import com.onarandombox.MultiverseCore.configuration.node.NodeGroup;
-import com.onarandombox.MultiverseCore.configuration.node.NodeSerializer;
 import com.onarandombox.MultiverseCore.configuration.node.ValueNode;
-import io.vavr.control.Option;
 import io.vavr.control.Try;
 import org.bukkit.configuration.ConfigurationSection;
 import org.bukkit.plugin.Plugin;
@@ -24,7 +22,7 @@ public abstract class GenericConfigHandle<C extends ConfigurationSection> {
 
     protected C config;
 
-    public GenericConfigHandle(@Nullable Logger logger, @Nullable NodeGroup nodes, @Nullable ConfigMigrator migrator) {
+    protected GenericConfigHandle(@Nullable Logger logger, @Nullable NodeGroup nodes, @Nullable ConfigMigrator migrator) {
         this.logger = logger;
         this.nodes = nodes;
         this.migrator = migrator;
@@ -33,12 +31,13 @@ public abstract class GenericConfigHandle<C extends ConfigurationSection> {
     /**
      * Loads the configuration.
      *
-     * @return True if the configuration was loaded successfully, false otherwise.
+     * @return Whether the configuration was loaded or its given error.
      */
-    public boolean load() {
-        migrateConfig();
-        setUpNodes();
-        return true;
+    public Try<Void> load() {
+        return Try.run(() -> {
+            migrateConfig();
+            setUpNodes();
+        });
     }
 
     /**
diff --git a/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/YamlConfigHandle.java b/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/YamlConfigHandle.java
index 0a6e2cbe..edbfc82f 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/YamlConfigHandle.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/configuration/handle/YamlConfigHandle.java
@@ -6,7 +6,7 @@ import java.util.logging.Logger;
 
 import com.onarandombox.MultiverseCore.configuration.migration.ConfigMigrator;
 import com.onarandombox.MultiverseCore.configuration.node.NodeGroup;
-import com.onarandombox.MultiverseCore.configuration.node.ValueNode;
+import io.vavr.control.Try;
 import org.bukkit.configuration.InvalidConfigurationException;
 import org.bukkit.configuration.file.YamlConfiguration;
 import org.jetbrains.annotations.NotNull;
@@ -35,27 +35,17 @@ public class YamlConfigHandle extends FileConfigHandle<YamlConfiguration> {
      * {@inheritDoc}
      */
     @Override
-    protected boolean loadConfigObject() {
+    protected void loadConfigObject() throws IOException, InvalidConfigurationException {
         config = new YamlConfiguration();
-        try {
-            config.load(configFile);
-        } catch (IOException | InvalidConfigurationException e) {
-            return false;
-        }
-        return true;
+        config.load(configFile);
     }
 
     /**
      * {@inheritDoc}
      */
     @Override
-    public boolean save() {
-        try {
-            config.save(configFile);
-        } catch (IOException e) {
-            return false;
-        }
-        return true;
+    public Try<Void> save() {
+        return Try.run(() -> config.save(configFile));
     }
 
     /**
diff --git a/src/main/java/com/onarandombox/MultiverseCore/worldnew/WorldManager.java b/src/main/java/com/onarandombox/MultiverseCore/worldnew/WorldManager.java
index 55830293..c66dcd5f 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/worldnew/WorldManager.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/worldnew/WorldManager.java
@@ -95,7 +95,9 @@ public class WorldManager {
      * Loads all worlds from the worlds config.
      */
     public void initAllWorlds() {
-        populateWorldFromConfig();
+        if (!populateWorldFromConfig()) {
+            return;
+        }
         loadDefaultWorlds();
         autoLoadOfflineWorlds();
         saveWorldsConfig();
@@ -104,8 +106,13 @@ public class WorldManager {
     /**
      * Generate offline worlds from the worlds config.
      */
-    private void populateWorldFromConfig() {
-        worldsConfigManager.load();
+    private boolean populateWorldFromConfig() {
+        Try<Void> load = worldsConfigManager.load();
+        if (load.isFailure()) {
+            Logging.severe("Failed to load worlds config: " + load.getCause().getMessage());
+            load.getCause().printStackTrace();
+            return false;
+        }
         worldsConfigManager.getAllWorldConfigs().forEach(worldConfig -> {
             getMVWorld(worldConfig.getWorldName())
                     .peek(mvWorld -> mvWorld.setWorldConfig(worldConfig));
@@ -116,6 +123,7 @@ public class WorldManager {
                         offlineWorldsMap.put(offlineWorld.getName(), offlineWorld);
                     });
         });
+        return true;
     }
 
     /**
@@ -785,6 +793,11 @@ public class WorldManager {
      * @return true if it had successfully saved the file.
      */
     public boolean saveWorldsConfig() {
-        return worldsConfigManager.save();
+        return worldsConfigManager.save()
+                .onFailure(failure -> {
+                    Logging.severe("Failed to save worlds config: %s", failure);
+                    failure.printStackTrace();
+                })
+                .isSuccess();
     }
 }
diff --git a/src/main/java/com/onarandombox/MultiverseCore/worldnew/config/WorldConfig.java b/src/main/java/com/onarandombox/MultiverseCore/worldnew/config/WorldConfig.java
index 2c1a116e..478457f9 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/worldnew/config/WorldConfig.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/worldnew/config/WorldConfig.java
@@ -35,7 +35,7 @@ public class WorldConfig {
         load();
     }
 
-    public boolean load() {
+    public Try<Void> load() {
         return configHandle.load();
     }
 
diff --git a/src/main/java/com/onarandombox/MultiverseCore/worldnew/config/WorldsConfigManager.java b/src/main/java/com/onarandombox/MultiverseCore/worldnew/config/WorldsConfigManager.java
index 74e1d694..bc0d642e 100644
--- a/src/main/java/com/onarandombox/MultiverseCore/worldnew/config/WorldsConfigManager.java
+++ b/src/main/java/com/onarandombox/MultiverseCore/worldnew/config/WorldsConfigManager.java
@@ -1,6 +1,7 @@
 package com.onarandombox.MultiverseCore.worldnew.config;
 
 import com.onarandombox.MultiverseCore.MultiverseCore;
+import io.vavr.control.Try;
 import jakarta.inject.Inject;
 import org.bukkit.configuration.ConfigurationSection;
 import org.bukkit.configuration.file.YamlConfiguration;
@@ -8,7 +9,6 @@ import org.jetbrains.annotations.NotNull;
 import org.jvnet.hk2.annotations.Service;
 
 import java.io.File;
-import java.io.IOException;
 import java.util.Collection;
 import java.util.HashMap;
 import java.util.Map;
@@ -23,32 +23,36 @@ public class WorldsConfigManager {
     private YamlConfiguration worldsConfig;
 
     @Inject
-    public WorldsConfigManager(@NotNull MultiverseCore core) {
+    WorldsConfigManager(@NotNull MultiverseCore core) {
         worldConfigMap = new HashMap<>();
         worldConfigFile = core.getDataFolder().toPath().resolve(CONFIG_FILENAME).toFile();
-        load();
     }
 
-    public void load() {
-        worldsConfig = YamlConfiguration.loadConfiguration(worldConfigFile);
+    public Try<Void> load() {
         worldConfigMap.clear();
-        for (String worldName : getAllWorldsInConfig()) {
-            worldConfigMap.put(worldName, new WorldConfig(worldName, getWorldConfigSection(worldName)));
-        }
+
+        return Try.run(() -> {
+            if (!worldConfigFile.exists()) {
+                worldConfigFile.createNewFile();
+            }
+            worldsConfig = new YamlConfiguration();
+            worldsConfig.load(worldConfigFile);
+        }).andThenTry(() -> {
+            for (String worldName : getAllWorldsInConfig()) {
+                worldConfigMap.put(worldName, new WorldConfig(worldName, getWorldConfigSection(worldName)));
+            }
+        }).onFailure(e -> {
+            worldsConfig = null;
+            worldConfigMap.clear();
+        });
     }
 
     public boolean isLoaded() {
         return worldsConfig != null;
     }
 
-    public boolean save() {
-        try {
-            worldsConfig.save(worldConfigFile);
-            return true;
-        } catch (IOException e) {
-            e.printStackTrace();
-        }
-        return false;
+    public Try<Void> save() {
+        return Try.run(() -> worldsConfig.save(worldConfigFile));
     }
 
     public Set<String> getAllWorldsInConfig() {
diff --git a/src/test/java/org/mvplugins/multiverse/core/config/ConfigTest.kt b/src/test/java/org/mvplugins/multiverse/core/config/ConfigTest.kt
index f8253bce..32d0d4b4 100644
--- a/src/test/java/org/mvplugins/multiverse/core/config/ConfigTest.kt
+++ b/src/test/java/org/mvplugins/multiverse/core/config/ConfigTest.kt
@@ -26,8 +26,8 @@ class ConfigTest : TestWithMockBukkit() {
         assertNotNull(defaultConfig)
         File(Path.of(multiverseCore.dataFolder.absolutePath, "config.yml").absolutePathString()).writeText(defaultConfig)
 
-        assertTrue(config.load())
-        assertTrue(config.save())
+        assertTrue(config.load().isSuccess)
+        assertTrue(config.save().isSuccess)
     }
 
     @Test
@@ -40,8 +40,8 @@ class ConfigTest : TestWithMockBukkit() {
         val oldConfig = getResourceAsText("/old_config.yml")
         assertNotNull(oldConfig)
         multiverseCore.dataFolder.toPath().resolve("config.yml").toFile().writeText(oldConfig)
-        assertTrue(config.load())
-        assertTrue(config.save())
+        assertTrue(config.load().isSuccess)
+        assertTrue(config.save().isSuccess)
 
         assertEquals(true, config.enforceAccess)
         assertEquals(false, config.isEnablePrefixChat)
diff --git a/src/test/java/org/mvplugins/multiverse/core/world/WorldConfigMangerTest.kt b/src/test/java/org/mvplugins/multiverse/core/world/WorldConfigMangerTest.kt
index d59994ed..822c1ac8 100644
--- a/src/test/java/org/mvplugins/multiverse/core/world/WorldConfigMangerTest.kt
+++ b/src/test/java/org/mvplugins/multiverse/core/world/WorldConfigMangerTest.kt
@@ -22,8 +22,10 @@ class WorldConfigMangerTest : TestWithMockBukkit() {
         assertNotNull(defaultConfig)
         File(Path.of(multiverseCore.dataFolder.absolutePath, "worlds2.yml").absolutePathString()).writeText(defaultConfig)
 
-        worldConfigManager =
-            WorldsConfigManager(multiverseCore)
+        worldConfigManager = multiverseCore.getService(WorldsConfigManager::class.java).takeIf { it != null } ?: run {
+            throw IllegalStateException("WorldsConfigManager is not available as a service") }
+
+        assertTrue(worldConfigManager.load().isSuccess)
     }
 
     @Test
diff --git a/src/test/java/org/mvplugins/multiverse/core/world/WorldConfigTest.kt b/src/test/java/org/mvplugins/multiverse/core/world/WorldConfigTest.kt
index 2c646c4d..113ab3c3 100644
--- a/src/test/java/org/mvplugins/multiverse/core/world/WorldConfigTest.kt
+++ b/src/test/java/org/mvplugins/multiverse/core/world/WorldConfigTest.kt
@@ -3,6 +3,7 @@ package org.mvplugins.multiverse.core.world
 import com.onarandombox.MultiverseCore.worldnew.config.WorldConfig
 import com.onarandombox.MultiverseCore.worldnew.config.WorldsConfigManager
 import org.bukkit.Location
+import org.junit.jupiter.api.Assertions
 import org.mvplugins.multiverse.core.TestWithMockBukkit
 import java.io.File
 import java.nio.file.Path
@@ -15,7 +16,7 @@ import kotlin.test.assertTrue
 
 class WorldConfigTest : TestWithMockBukkit() {
 
-    private lateinit var worldConfigFile : WorldsConfigManager
+    private lateinit var worldConfigManager : WorldsConfigManager
     private lateinit var worldConfig : WorldConfig
 
     @BeforeTest
@@ -24,9 +25,12 @@ class WorldConfigTest : TestWithMockBukkit() {
         assertNotNull(defaultConfig)
         File(Path.of(multiverseCore.dataFolder.absolutePath, "worlds2.yml").absolutePathString()).writeText(defaultConfig)
 
-        worldConfigFile =
-            WorldsConfigManager(multiverseCore)
-        worldConfig = worldConfigFile.getWorldConfig("world")
+        worldConfigManager = multiverseCore.getService(WorldsConfigManager::class.java).takeIf { it != null } ?: run {
+            throw IllegalStateException("WorldsConfigManager is not available as a service") }
+
+        assertTrue(worldConfigManager.load().isSuccess)
+        worldConfig = worldConfigManager.getWorldConfig("world")
+        assertNotNull(worldConfig);
     }
 
     @Test