diff --git a/paper-api/src/main/java/org/bukkit/plugin/SimplePluginManager.java b/paper-api/src/main/java/org/bukkit/plugin/SimplePluginManager.java
index 6619236600..8682f341b4 100644
--- a/paper-api/src/main/java/org/bukkit/plugin/SimplePluginManager.java
+++ b/paper-api/src/main/java/org/bukkit/plugin/SimplePluginManager.java
@@ -1,6 +1,10 @@
 package org.bukkit.plugin;
 
+import com.google.common.base.Preconditions;
 import com.google.common.collect.ImmutableSet;
+import com.google.common.graph.GraphBuilder;
+import com.google.common.graph.Graphs;
+import com.google.common.graph.MutableGraph;
 import java.io.File;
 import java.lang.reflect.Constructor;
 import java.lang.reflect.Method;
@@ -44,6 +48,7 @@ public final class SimplePluginManager implements PluginManager {
     private final Map<Pattern, PluginLoader> fileAssociations = new HashMap<Pattern, PluginLoader>();
     private final List<Plugin> plugins = new ArrayList<Plugin>();
     private final Map<String, Plugin> lookupNames = new HashMap<String, Plugin>();
+    private MutableGraph<String> dependencyGraph = GraphBuilder.directed().build();
     private File updateDirectory;
     private final SimpleCommandMap commandMap;
     private final Map<String, Permission> permissions = new HashMap<String, Permission>();
@@ -168,11 +173,19 @@ public final class SimplePluginManager implements PluginManager {
                 } else {
                     softDependencies.put(description.getName(), new LinkedList<String>(softDependencySet));
                 }
+
+                for (String depend : softDependencySet) {
+                    dependencyGraph.putEdge(description.getName(), depend);
+                }
             }
 
             Collection<String> dependencySet = description.getDepend();
             if (dependencySet != null && !dependencySet.isEmpty()) {
                 dependencies.put(description.getName(), new LinkedList<String>(dependencySet));
+
+                for (String depend : dependencySet) {
+                    dependencyGraph.putEdge(description.getName(), depend);
+                }
             }
 
             Collection<String> loadBeforeSet = description.getLoadBefore();
@@ -186,6 +199,8 @@ public final class SimplePluginManager implements PluginManager {
                         shortSoftDependency.add(description.getName());
                         softDependencies.put(loadBeforeTarget, shortSoftDependency);
                     }
+
+                    dependencyGraph.putEdge(loadBeforeTarget, description.getName());
                 }
             }
         }
@@ -480,6 +495,7 @@ public final class SimplePluginManager implements PluginManager {
             disablePlugins();
             plugins.clear();
             lookupNames.clear();
+            dependencyGraph = GraphBuilder.directed().build();
             HandlerList.unregisterAll();
             fileAssociations.clear();
             permissions.clear();
@@ -780,6 +796,13 @@ public final class SimplePluginManager implements PluginManager {
         return new HashSet<Permission>(permissions.values());
     }
 
+    public boolean isTransitiveDepend(@NotNull PluginDescriptionFile plugin, @NotNull Plugin depend) {
+        Preconditions.checkArgument(plugin != null, "plugin");
+        Preconditions.checkArgument(depend != null, "depend");
+
+        return Graphs.reachableNodes(dependencyGraph, plugin.getName()).contains(depend.getName());
+    }
+
     @Override
     public boolean useTimings() {
         return useTimings;
diff --git a/paper-api/src/main/java/org/bukkit/plugin/java/PluginClassLoader.java b/paper-api/src/main/java/org/bukkit/plugin/java/PluginClassLoader.java
index c6633ee7d9..bd10ca723f 100644
--- a/paper-api/src/main/java/org/bukkit/plugin/java/PluginClassLoader.java
+++ b/paper-api/src/main/java/org/bukkit/plugin/java/PluginClassLoader.java
@@ -22,6 +22,7 @@ import java.util.logging.Level;
 import org.apache.commons.lang.Validate;
 import org.bukkit.plugin.InvalidPluginException;
 import org.bukkit.plugin.PluginDescriptionFile;
+import org.bukkit.plugin.SimplePluginManager;
 import org.jetbrains.annotations.NotNull;
 import org.jetbrains.annotations.Nullable;
 
@@ -113,12 +114,15 @@ final class PluginClassLoader extends URLClassLoader {
 
                     if (provider != plugin
                             && !seenIllegalAccess.contains(providerName)
-                            && !description.getDepend().contains(providerName)
-                            && !description.getSoftDepend().contains(providerName)
-                            && !provider.getDescription().getLoadBefore().contains(description.getName())) {
+                            && !((SimplePluginManager) loader.server.getPluginManager()).isTransitiveDepend(description, provider)) {
 
                         seenIllegalAccess.add(providerName);
-                        plugin.getLogger().log(Level.WARNING, "Loaded class {0} from {1} which is not a depend, softdepend or loadbefore of this plugin.", new Object[]{name, provider.getDescription().getFullName()});
+                        if (plugin != null) {
+                            plugin.getLogger().log(Level.WARNING, "Loaded class {0} from {1} which is not a depend, softdepend or loadbefore of this plugin.", new Object[]{name, provider.getDescription().getFullName()});
+                        } else {
+                            // In case the bad access occurs on construction
+                            loader.server.getLogger().log(Level.WARNING, "[{0}] Loaded class {1} from {2} which is not a depend, softdepend or loadbefore of this plugin.", new Object[]{description.getName(), name, provider.getDescription().getFullName()});
+                        }
                     }
                 }
             }