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 7d0ebd2c47..eb8d47d071 100644
--- a/paper-api/src/main/java/org/bukkit/plugin/SimplePluginManager.java
+++ b/paper-api/src/main/java/org/bukkit/plugin/SimplePluginManager.java
@@ -249,7 +249,7 @@ public final class SimplePluginManager implements PluginManager {
             try {
                 plugin.getPluginLoader().enablePlugin(plugin);
             } catch (Throwable ex) {
-                server.getLogger().log(Level.SEVERE, ex.getMessage() + " enabling " + plugin.getDescription().getFullName() + " (Is it up to date?)", ex);
+                server.getLogger().log(Level.SEVERE, "Error occurred (in the plugin loader) while enabling " + plugin.getDescription().getFullName() + " (Is it up to date?): " + ex.getMessage(), ex);
             }
         }
     }
@@ -264,11 +264,13 @@ public final class SimplePluginManager implements PluginManager {
         if (plugin.isEnabled()) {
             try {
                 plugin.getPluginLoader().disablePlugin(plugin);
-                server.getScheduler().cancelTasks(plugin);
-                server.getServicesManager().unregisterAll(plugin);
             } catch (Throwable ex) {
-                server.getLogger().log(Level.SEVERE, ex.getMessage() + " disabling " + plugin.getDescription().getFullName() + " (Is it up to date?)", ex);
+                server.getLogger().log(Level.SEVERE, "Error occurredd (in the plugin loader) while disabling " + plugin.getDescription().getFullName() + " (Is it up to date?): " + ex.getMessage(), ex);
             }
+            
+            // Forced disable
+            server.getScheduler().cancelTasks(plugin);
+            server.getServicesManager().unregisterAll(plugin);
         }
     }
 
diff --git a/paper-api/src/main/java/org/bukkit/plugin/java/JavaPluginLoader.java b/paper-api/src/main/java/org/bukkit/plugin/java/JavaPluginLoader.java
index f38b7d1f5b..fa54be7215 100644
--- a/paper-api/src/main/java/org/bukkit/plugin/java/JavaPluginLoader.java
+++ b/paper-api/src/main/java/org/bukkit/plugin/java/JavaPluginLoader.java
@@ -673,7 +673,15 @@ public final class JavaPluginLoader implements PluginLoader {
                 loaders.put(pluginName, (PluginClassLoader)jPlugin.getClassLoader());
             }
 
-            jPlugin.setEnabled(true);
+            try {
+                jPlugin.setEnabled(true);
+            } catch (Throwable ex) {
+                server.getLogger().log(Level.SEVERE, "Error occurred while enabling " + plugin.getDescription().getFullName() + " (Is it up to date?): " + ex.getMessage(), ex);
+            }
+            
+            // Perhaps abort here, rather than continue going, but as it stands,
+            // an abort is not possible the way it's currently written
+            
             server.getPluginManager().callEvent(new PluginEnableEvent(plugin));
         }
     }
@@ -687,7 +695,11 @@ public final class JavaPluginLoader implements PluginLoader {
             JavaPlugin jPlugin = (JavaPlugin)plugin;
             ClassLoader cloader = jPlugin.getClassLoader();
 
-            jPlugin.setEnabled(false);
+            try {
+                jPlugin.setEnabled(false);
+            } catch (Throwable ex) {
+                server.getLogger().log(Level.SEVERE, "Error occurred while disabling " + plugin.getDescription().getFullName() + " (Is it up to date?): " + ex.getMessage(), ex);
+            }
 
             server.getPluginManager().callEvent(new PluginDisableEvent(plugin));