diff --git a/Plan/bukkit/src/main/java/com/djrapitops/plan/modules/bukkit/BukkitTaskModule.java b/Plan/bukkit/src/main/java/com/djrapitops/plan/modules/bukkit/BukkitTaskModule.java
index b817aee32..e52ec1048 100644
--- a/Plan/bukkit/src/main/java/com/djrapitops/plan/modules/bukkit/BukkitTaskModule.java
+++ b/Plan/bukkit/src/main/java/com/djrapitops/plan/modules/bukkit/BukkitTaskModule.java
@@ -27,6 +27,7 @@ import com.djrapitops.plan.gathering.timed.SystemUsageBuffer;
 import com.djrapitops.plan.settings.upkeep.ConfigStoreTask;
 import com.djrapitops.plan.storage.upkeep.DBCleanTask;
 import com.djrapitops.plan.storage.upkeep.LogsFolderCleanTask;
+import com.djrapitops.plan.storage.upkeep.OldDependencyCacheDeletionTask;
 import dagger.Binds;
 import dagger.Module;
 import dagger.multibindings.IntoSet;
@@ -79,4 +80,7 @@ public interface BukkitTaskModule {
     @IntoSet
     TaskSystem.Task bindShutdownDataPreservation(ShutdownDataPreservation dataPreservation);
 
+    @Binds
+    @IntoSet
+    TaskSystem.Task bindOldDependencyCacheDeletion(OldDependencyCacheDeletionTask deletionTask);
 }
diff --git a/Plan/bungeecord/src/main/java/com/djrapitops/plan/modules/bungee/BungeeTaskModule.java b/Plan/bungeecord/src/main/java/com/djrapitops/plan/modules/bungee/BungeeTaskModule.java
index c155abf78..1fb9697cc 100644
--- a/Plan/bungeecord/src/main/java/com/djrapitops/plan/modules/bungee/BungeeTaskModule.java
+++ b/Plan/bungeecord/src/main/java/com/djrapitops/plan/modules/bungee/BungeeTaskModule.java
@@ -25,6 +25,7 @@ import com.djrapitops.plan.gathering.timed.SystemUsageBuffer;
 import com.djrapitops.plan.settings.upkeep.NetworkConfigStoreTask;
 import com.djrapitops.plan.storage.upkeep.DBCleanTask;
 import com.djrapitops.plan.storage.upkeep.LogsFolderCleanTask;
+import com.djrapitops.plan.storage.upkeep.OldDependencyCacheDeletionTask;
 import dagger.Binds;
 import dagger.Module;
 import dagger.multibindings.IntoSet;
@@ -67,4 +68,8 @@ public interface BungeeTaskModule {
     @Binds
     @IntoSet
     TaskSystem.Task bindJSONFileStorageCleanTask(JSONFileStorage.CleanTask cleanTask);
+
+    @Binds
+    @IntoSet
+    TaskSystem.Task bindOldDependencyCacheDeletion(OldDependencyCacheDeletionTask deletionTask);
 }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/LogsFolderCleanTask.java b/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/LogsFolderCleanTask.java
index 59c973972..b361744d3 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/LogsFolderCleanTask.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/LogsFolderCleanTask.java
@@ -29,7 +29,6 @@ import javax.inject.Singleton;
 import java.io.File;
 import java.io.IOException;
 import java.nio.file.Files;
-import java.util.Objects;
 import java.util.concurrent.TimeUnit;
 
 /**
@@ -81,7 +80,9 @@ public class LogsFolderCleanTask extends TaskSystem.Task {
 
     private void cleanFolder() {
         long now = System.currentTimeMillis();
-        for (File file : Objects.requireNonNull(folder.listFiles())) {
+        File[] files = folder.listFiles();
+        if (files == null) return;
+        for (File file : files) {
             long forDaysMs = TimeUnit.DAYS.toMillis(config.get(PluginSettings.KEEP_LOGS_DAYS));
             if (now - file.lastModified() > (forDaysMs > 0 ? forDaysMs : TimeUnit.DAYS.toMillis(1L))) {
                 try {
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/OldDependencyCacheDeletionTask.java b/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/OldDependencyCacheDeletionTask.java
new file mode 100644
index 000000000..0db243db2
--- /dev/null
+++ b/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/OldDependencyCacheDeletionTask.java
@@ -0,0 +1,86 @@
+/*
+ *  This file is part of Player Analytics (Plan).
+ *
+ *  Plan is free software: you can redistribute it and/or modify
+ *  it under the terms of the GNU Lesser General Public License v3 as published by
+ *  the Free Software Foundation, either version 3 of the License, or
+ *  (at your option) any later version.
+ *
+ *  Plan 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 Lesser General Public License for more details.
+ *
+ *  You should have received a copy of the GNU Lesser General Public License
+ *  along with Plan. If not, see <https://www.gnu.org/licenses/>.
+ */
+package com.djrapitops.plan.storage.upkeep;
+
+import com.djrapitops.plan.TaskSystem;
+import com.djrapitops.plan.storage.file.PlanFiles;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
+import com.djrapitops.plan.utilities.logging.ErrorLogger;
+import net.playeranalytics.plugin.scheduling.RunnableFactory;
+import net.playeranalytics.plugin.scheduling.TimeAmount;
+
+import javax.inject.Inject;
+import javax.inject.Singleton;
+import java.io.File;
+import java.io.IOException;
+import java.nio.file.Files;
+import java.util.concurrent.TimeUnit;
+
+@Singleton
+public class OldDependencyCacheDeletionTask extends TaskSystem.Task {
+
+    private final File dependencyCache;
+    private final File libraries;
+
+    private final ErrorLogger errorLogger;
+
+    @Inject
+    public OldDependencyCacheDeletionTask(
+            PlanFiles files,
+            ErrorLogger errorLogger
+    ) {
+        dependencyCache = files.getDataDirectory().resolve("dependency_cache").toFile();
+        libraries = files.getDataDirectory().resolve("libraries").toFile();
+        this.errorLogger = errorLogger;
+    }
+
+    @Override
+    public void register(RunnableFactory runnableFactory) {
+        long delay = TimeAmount.toTicks(10L, TimeUnit.SECONDS);
+        runnableFactory.create(this).runTaskLaterAsynchronously(delay);
+    }
+
+    @Override
+    public void run() {
+        tryToDeleteDirectory(dependencyCache);
+        tryToDeleteDirectory(libraries);
+    }
+
+    private void tryToDeleteDirectory(File directory) {
+        try {
+            if (directory.exists() && directory.isDirectory()) {
+                deleteDirectory(directory);
+            }
+        } catch (IOException e) {
+            errorLogger.error(e, ErrorContext.builder()
+                    .whatToDo("Failed to delete '" + directory.getAbsolutePath() + "' - Delete it manually.")
+                    .build());
+        }
+    }
+
+    private void deleteDirectory(File directory) throws IOException {
+        File[] files = directory.listFiles();
+        if (files == null) return;
+        for (File file : files) {
+            if (file.isDirectory()) {
+                deleteDirectory(directory);
+            } else {
+                Files.delete(file.toPath());
+            }
+        }
+    }
+}
diff --git a/Plan/nukkit/src/main/java/com/djrapitops/plan/modules/nukkit/NukkitTaskModule.java b/Plan/nukkit/src/main/java/com/djrapitops/plan/modules/nukkit/NukkitTaskModule.java
index dfcdff7b2..eb6c8116a 100644
--- a/Plan/nukkit/src/main/java/com/djrapitops/plan/modules/nukkit/NukkitTaskModule.java
+++ b/Plan/nukkit/src/main/java/com/djrapitops/plan/modules/nukkit/NukkitTaskModule.java
@@ -28,6 +28,7 @@ import com.djrapitops.plan.gathering.timed.SystemUsageBuffer;
 import com.djrapitops.plan.settings.upkeep.ConfigStoreTask;
 import com.djrapitops.plan.storage.upkeep.DBCleanTask;
 import com.djrapitops.plan.storage.upkeep.LogsFolderCleanTask;
+import com.djrapitops.plan.storage.upkeep.OldDependencyCacheDeletionTask;
 import dagger.Binds;
 import dagger.Module;
 import dagger.multibindings.IntoSet;
@@ -78,4 +79,8 @@ public interface NukkitTaskModule {
     @Binds
     @IntoSet
     TaskSystem.Task bindShutdownDataPreservation(ShutdownDataPreservation dataPreservation);
+
+    @Binds
+    @IntoSet
+    TaskSystem.Task bindOldDependencyCacheDeletion(OldDependencyCacheDeletionTask deletionTask);
 }
diff --git a/Plan/sponge/src/main/java/com/djrapitops/plan/modules/sponge/SpongeTaskModule.java b/Plan/sponge/src/main/java/com/djrapitops/plan/modules/sponge/SpongeTaskModule.java
index 4fbe926d6..0cf624f56 100644
--- a/Plan/sponge/src/main/java/com/djrapitops/plan/modules/sponge/SpongeTaskModule.java
+++ b/Plan/sponge/src/main/java/com/djrapitops/plan/modules/sponge/SpongeTaskModule.java
@@ -27,6 +27,7 @@ import com.djrapitops.plan.gathering.timed.SystemUsageBuffer;
 import com.djrapitops.plan.settings.upkeep.ConfigStoreTask;
 import com.djrapitops.plan.storage.upkeep.DBCleanTask;
 import com.djrapitops.plan.storage.upkeep.LogsFolderCleanTask;
+import com.djrapitops.plan.storage.upkeep.OldDependencyCacheDeletionTask;
 import dagger.Binds;
 import dagger.Module;
 import dagger.multibindings.IntoSet;
@@ -78,4 +79,8 @@ public interface SpongeTaskModule {
     @Binds
     @IntoSet
     TaskSystem.Task bindShutdownDataPreservation(ShutdownDataPreservation dataPreservation);
+
+    @Binds
+    @IntoSet
+    TaskSystem.Task bindOldDependencyCacheDeletion(OldDependencyCacheDeletionTask deletionTask);
 }
diff --git a/Plan/velocity/src/main/java/com/djrapitops/plan/modules/velocity/VelocityTaskModule.java b/Plan/velocity/src/main/java/com/djrapitops/plan/modules/velocity/VelocityTaskModule.java
index 1bc5351f9..c0839c59d 100644
--- a/Plan/velocity/src/main/java/com/djrapitops/plan/modules/velocity/VelocityTaskModule.java
+++ b/Plan/velocity/src/main/java/com/djrapitops/plan/modules/velocity/VelocityTaskModule.java
@@ -25,6 +25,7 @@ import com.djrapitops.plan.gathering.timed.VelocityPingCounter;
 import com.djrapitops.plan.settings.upkeep.NetworkConfigStoreTask;
 import com.djrapitops.plan.storage.upkeep.DBCleanTask;
 import com.djrapitops.plan.storage.upkeep.LogsFolderCleanTask;
+import com.djrapitops.plan.storage.upkeep.OldDependencyCacheDeletionTask;
 import dagger.Binds;
 import dagger.Module;
 import dagger.multibindings.IntoSet;
@@ -67,4 +68,8 @@ public interface VelocityTaskModule {
     @Binds
     @IntoSet
     TaskSystem.Task bindJSONFileStorageCleanTask(JSONFileStorage.CleanTask cleanTask);
+
+    @Binds
+    @IntoSet
+    TaskSystem.Task bindOldDependencyCacheDeletion(OldDependencyCacheDeletionTask deletionTask);
 }