diff --git a/Essentials/build.gradle b/Essentials/build.gradle
index d04d2800dca..b410742cd23 100644
--- a/Essentials/build.gradle
+++ b/Essentials/build.gradle
@@ -7,6 +7,7 @@ dependencies {
         exclude group: "org.bukkit", module: "bukkit"
     }
     compileOnly 'net.luckperms:api:5.3'
+    compileOnly 'org.apache.logging.log4j:log4j-core:2.17.1'
 
     api 'io.papermc:paperlib:1.0.6'
 
diff --git a/Essentials/src/main/java/com/earth2me/essentials/AlternativeCommandsHandler.java b/Essentials/src/main/java/com/earth2me/essentials/AlternativeCommandsHandler.java
index 01f7fa3caf0..dab484339c0 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/AlternativeCommandsHandler.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/AlternativeCommandsHandler.java
@@ -1,6 +1,6 @@
 package com.earth2me.essentials;
 
-import java.util.stream.Collectors;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import net.ess3.provider.KnownCommandsProvider;
 import org.bukkit.command.Command;
 import org.bukkit.command.PluginIdentifiableCommand;
@@ -13,7 +13,7 @@
 import java.util.List;
 import java.util.Locale;
 import java.util.Map;
-import java.util.logging.Level;
+import java.util.stream.Collectors;
 
 public class AlternativeCommandsHandler {
     private final transient Map<String, List<WeakReference<Command>>> altCommands = new HashMap<>();
@@ -45,9 +45,7 @@ public final void addPlugin(final Plugin plugin) {
             while (pluginCmdIterator.hasNext()) {
                 final Command cmd = pluginCmdIterator.next().get();
                 if (cmd == null) {
-                    if (ess.getSettings().isDebug()) {
-                        ess.getLogger().log(Level.INFO, "Essentials: Alternative command for " + commandName + " removed due to garbage collection");
-                    }
+                    DebugLogUtil.debugLog("Essentials: Alternative command for " + commandName + " removed due to garbage collection");
 
                     pluginCmdIterator.remove();
                     continue;
@@ -136,9 +134,7 @@ public Command getAlternative(final String label) {
     public void executed(final String label, final Command pc) {
         if (pc instanceof PluginIdentifiableCommand) {
             final String altString = ((PluginIdentifiableCommand) pc).getPlugin().getName() + ":" + pc.getName();
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.INFO, "Essentials: Alternative command " + label + " found, using " + altString);
-            }
+            DebugLogUtil.debugLog("Essentials: Alternative command " + label + " found, using " + altString);
             disabledList.put(label, altString);
         }
     }
diff --git a/Essentials/src/main/java/com/earth2me/essentials/AsyncTeleport.java b/Essentials/src/main/java/com/earth2me/essentials/AsyncTeleport.java
index fc98e97e175..02f5e1ab01a 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/AsyncTeleport.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/AsyncTeleport.java
@@ -3,6 +3,7 @@
 import com.earth2me.essentials.api.IAsyncTeleport;
 import com.earth2me.essentials.commands.WarpNotFoundException;
 import com.earth2me.essentials.utils.DateUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.LocationUtil;
 import io.papermc.lib.PaperLib;
 import net.ess3.api.IEssentials;
@@ -398,9 +399,7 @@ void respawnNow(final IUser teleportee, final TeleportCause cause, final Complet
             if (location != null) {
                 nowAsync(teleportee, new LocationTarget(location), cause, future);
             } else {
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().info("Could not find bed spawn, forcing respawn event.");
-                }
+                DebugLogUtil.debugLog("Could not find bed spawn, forcing respawn event.");
                 final PlayerRespawnEvent pre = new PlayerRespawnEvent(player, player.getWorld().getSpawnLocation(), false);
                 ess.getServer().getPluginManager().callEvent(pre);
                 nowAsync(teleportee, new LocationTarget(pre.getRespawnLocation()), cause, future);
diff --git a/Essentials/src/main/java/com/earth2me/essentials/Essentials.java b/Essentials/src/main/java/com/earth2me/essentials/Essentials.java
index 39c7a596612..0aef3a44139 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/Essentials.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/Essentials.java
@@ -41,6 +41,7 @@
 import com.earth2me.essentials.updatecheck.UpdateChecker;
 import com.earth2me.essentials.userstorage.ModernUserMap;
 import com.earth2me.essentials.utils.AdventureUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.earth2me.essentials.utils.VersionUtil;
 import io.papermc.lib.PaperLib;
@@ -206,6 +207,7 @@ public ISettings getSettings() {
     public void setupForTesting(final Server server) throws IOException, InvalidDescriptionException {
         TESTING = true;
         LOGGER = new BaseLoggerProvider(this, BUKKIT_LOGGER);
+        DebugLogUtil.setEssentials(this);
         final File dataFolder = File.createTempFile("essentialstest", "");
         if (!dataFolder.delete()) {
             throw new IOException();
@@ -437,9 +439,7 @@ public void onEnable() {
                             ((Cancellable) event).setCancelled(true);
                         }
                     });
-                    if (getSettings().isDebug()) {
-                        LOGGER.log(Level.INFO, "Registered Paper Recipe Book Event Listener");
-                    }
+                    DebugLogUtil.debugLog("Registered Paper Recipe Book Event Listener");
                 } catch (final ClassNotFoundException ignored) {
                 }
             }
@@ -458,6 +458,7 @@ public void onEnable() {
             scheduleSyncRepeatingTask(timer, 1000, 50);
 
             Economy.setEss(this);
+            DebugLogUtil.setEssentials(this);
             execTimer.mark("RegHandler");
 
             // Register /hat and /back default permissions
@@ -477,9 +478,7 @@ public void onEnable() {
             execTimer.mark("Init(External)");
 
             final String timeroutput = execTimer.end();
-            if (getSettings().isDebug()) {
-                LOGGER.log(Level.INFO, "Essentials load " + timeroutput);
-            }
+            DebugLogUtil.debugLog("Essentials load " + timeroutput);
         } catch (final NumberFormatException ex) {
             handleCrash(ex);
         } catch (final Error ex) {
@@ -506,9 +505,7 @@ public void saveConfig() {
     private void registerListeners(final PluginManager pm) {
         HandlerList.unregisterAll(this);
 
-        if (getSettings().isDebug()) {
-            LOGGER.log(Level.INFO, "Registering Listeners");
-        }
+        DebugLogUtil.debugLog("Registering Listeners");
 
         final EssentialsPluginListener pluginListener = new EssentialsPluginListener(this);
         pm.registerEvents(pluginListener, this);
@@ -589,6 +586,7 @@ public void onDisable() {
         this.getPermissionsHandler().unregisterContexts();
 
         Economy.setEss(null);
+        DebugLogUtil.setEssentials(null);
         Trade.closeLog();
         getUsers().shutdown();
 
@@ -729,9 +727,7 @@ public boolean onCommand(final CommandSender sender, final Command command, fina
     public boolean onCommandEssentials(final CommandSender cSender, final Command command, final String commandLabel, final String[] args, final ClassLoader classLoader, final String commandPath, final String permissionPrefix, final IEssentialsModule module) {
         // Allow plugins to override the command via onCommand
         if (!getSettings().isCommandOverridden(command.getName()) && (!commandLabel.startsWith("e") || commandLabel.equalsIgnoreCase(command.getName()))) {
-            if (getSettings().isDebug()) {
-                LOGGER.log(Level.INFO, "Searching for alternative to: " + commandLabel);
-            }
+            DebugLogUtil.debugLog("Searching for alternative to: " + commandLabel);
             final Command pc = alternativeCommandsHandler.getAlternative(commandLabel);
             if (pc != null) {
                 alternativeCommandsHandler.executed(commandLabel, pc);
@@ -893,9 +889,7 @@ public void showError(final CommandSource sender, final Throwable exception, fin
         } else {
             sender.sendTl("errorWithMessage", exception.getMessage());
         }
-        if (getSettings().isDebug()) {
-            LOGGER.log(Level.INFO, AdventureUtil.miniToLegacy(tlLiteral("errorCallingCommand", commandLabel)), exception);
-        }
+        DebugLogUtil.debugLog(AdventureUtil.miniToLegacy(tlLiteral("errorCallingCommand", commandLabel)), exception);
     }
 
     @Override
diff --git a/Essentials/src/main/java/com/earth2me/essentials/EssentialsPlayerListener.java b/Essentials/src/main/java/com/earth2me/essentials/EssentialsPlayerListener.java
index 8b6b2d51f16..93f4d2aa713 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/EssentialsPlayerListener.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/EssentialsPlayerListener.java
@@ -9,6 +9,7 @@
 import com.earth2me.essentials.utils.AdventureUtil;
 import com.earth2me.essentials.utils.CommonPlaceholders;
 import com.earth2me.essentials.utils.DateUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.earth2me.essentials.utils.LocationUtil;
 import com.earth2me.essentials.utils.MaterialUtil;
@@ -203,11 +204,8 @@ public void onPlayerChat(final AsyncPlayerChatEvent event) {
                 }
             }
         } catch (final UnsupportedOperationException ex) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.INFO, "Ignore could not block chat due to custom chat plugin event.", ex);
-            } else {
-                ess.getLogger().info("Ignore could not block chat due to custom chat plugin event.");
-            }
+            DebugLogUtil.debugLog("Ignore could not block chat due to custom chat plugin event.", ex);
+            ess.getLogger().info("Ignore could not block chat due to custom chat plugin event.");
         }
 
         user.updateActivityOnChat(true);
@@ -383,9 +381,7 @@ public void run() {
                         final Player toVanish = ess.getServer().getPlayerExact(p);
                         if (toVanish != null && toVanish.isOnline()) {
                             user.getBase().hidePlayer(toVanish);
-                            if (ess.getSettings().isDebug()) {
-                                ess.getLogger().info("Hiding vanished player: " + p);
-                            }
+                            DebugLogUtil.debugLog("Hiding vanished player: " + p);
                         }
                     }
                 }
@@ -501,11 +497,8 @@ public void run() {
                         try {
                             tempInput = new TextInput(user.getSource(), "motd", true, ess);
                         } catch (final IOException ex) {
-                            if (ess.getSettings().isDebug()) {
-                                ess.getLogger().log(Level.WARNING, ex.getMessage(), ex);
-                            } else {
-                                ess.getLogger().log(Level.WARNING, ex.getMessage());
-                            }
+                            DebugLogUtil.debugLog(ex.getMessage(), ex);
+                            ess.getLogger().log(Level.WARNING, ex.getMessage());
                         }
                     }
 
@@ -741,9 +734,7 @@ public void handlePlayerCommandPreprocess(final PlayerCommandPreprocessEvent eve
                 final Entry<Pattern, Long> cooldownEntry = ess.getSettings().getCommandCooldownEntry(fullCommand);
 
                 if (cooldownEntry != null) {
-                    if (ess.getSettings().isDebug()) {
-                        ess.getLogger().info("Applying " + cooldownEntry.getValue() + "ms cooldown on /" + fullCommand + " for" + user.getName() + ".");
-                    }
+                    DebugLogUtil.debugLog("Applying " + cooldownEntry.getValue() + "ms cooldown on /" + fullCommand + " for" + user.getName() + ".");
                     final Date expiry = new Date(System.currentTimeMillis() + cooldownEntry.getValue());
                     user.addCommandCooldown(cooldownEntry.getKey(), expiry, ess.getSettings().isCommandCooldownPersistent(fullCommand));
                 }
@@ -881,9 +872,7 @@ public void run() {
 
             ess.scheduleSyncDelayedTask(new DelayedClickJumpTask());
         } catch (final Exception ex) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.WARNING, ex.getMessage(), ex);
-            }
+            DebugLogUtil.debugLog(ex.getMessage(), ex);
         }
     }
 
diff --git a/Essentials/src/main/java/com/earth2me/essentials/Jails.java b/Essentials/src/main/java/com/earth2me/essentials/Jails.java
index f4e31f09692..3e229a94f54 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/Jails.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/Jails.java
@@ -4,6 +4,7 @@
 import com.earth2me.essentials.config.EssentialsConfiguration;
 import com.earth2me.essentials.config.entities.LazyLocation;
 import com.earth2me.essentials.utils.AdventureUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import net.ess3.api.IEssentials;
 import net.ess3.api.IUser;
 import net.ess3.api.TranslatableException;
@@ -75,9 +76,7 @@ private void registerListeners() {
         final PluginManager pluginManager = ess.getServer().getPluginManager();
         final JailListener blockListener = new JailListener();
         pluginManager.registerEvents(blockListener, ess);
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().log(Level.INFO, "Registering Jail listener");
-        }
+        DebugLogUtil.debugLog("Registering Jail listener");
     }
 
     public void resetListener() {
@@ -272,11 +271,8 @@ public void onJailPlayerRespawn(final PlayerRespawnEvent event) {
             try {
                 event.setRespawnLocation(getJail(user.getJail()));
             } catch (final Exception ex) {
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().log(Level.INFO, AdventureUtil.miniToLegacy(tlLiteral("returnPlayerToJailError", user.getName(), ex.getLocalizedMessage())), ex);
-                } else {
-                    ess.getLogger().log(Level.INFO, AdventureUtil.miniToLegacy(tlLiteral("returnPlayerToJailError", user.getName(), ex.getLocalizedMessage())));
-                }
+                DebugLogUtil.debugLog(AdventureUtil.miniToLegacy(tlLiteral("returnPlayerToJailError", user.getName(), ex.getLocalizedMessage())), ex);
+                ess.getLogger().log(Level.INFO, AdventureUtil.miniToLegacy(tlLiteral("returnPlayerToJailError", user.getName(), ex.getLocalizedMessage())));
             }
         }
 
@@ -294,11 +290,8 @@ public void onJailPlayerTeleport(final PlayerTeleportEvent event) {
             try {
                 event.setTo(getJail(user.getJail()));
             } catch (final Exception ex) {
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().log(Level.INFO, AdventureUtil.miniToLegacy(tlLiteral("returnPlayerToJailError", user.getName(), ex.getLocalizedMessage())), ex);
-                } else {
-                    ess.getLogger().log(Level.INFO, AdventureUtil.miniToLegacy(tlLiteral("returnPlayerToJailError", user.getName(), ex.getLocalizedMessage())));
-                }
+                DebugLogUtil.debugLog(AdventureUtil.miniToLegacy(tlLiteral("returnPlayerToJailError", user.getName(), ex.getLocalizedMessage())), ex);
+                ess.getLogger().log(Level.INFO, AdventureUtil.miniToLegacy(tlLiteral("returnPlayerToJailError", user.getName(), ex.getLocalizedMessage())));
             }
             user.sendTl("jailMessage");
         }
@@ -318,11 +311,8 @@ public void onJailPlayerJoin(final PlayerJoinEvent event) {
 
             final CompletableFuture<Boolean> future = new CompletableFuture<>();
             future.exceptionally(ex -> {
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().log(Level.INFO, AdventureUtil.miniToLegacy(tlLiteral("returnPlayerToJailError", user.getName(), ex.getLocalizedMessage())), ex);
-                } else {
-                    ess.getLogger().log(Level.INFO, AdventureUtil.miniToLegacy(tlLiteral("returnPlayerToJailError", user.getName(), ex.getLocalizedMessage())));
-                }
+                DebugLogUtil.debugLog(AdventureUtil.miniToLegacy(tlLiteral("returnPlayerToJailError", user.getName(), ex.getLocalizedMessage())), ex);
+                ess.getLogger().log(Level.INFO, AdventureUtil.miniToLegacy(tlLiteral("returnPlayerToJailError", user.getName(), ex.getLocalizedMessage())));
                 return false;
             });
             future.thenAccept(success -> user.sendTl("jailMessage"));
diff --git a/Essentials/src/main/java/com/earth2me/essentials/MetaItemStack.java b/Essentials/src/main/java/com/earth2me/essentials/MetaItemStack.java
index 8347c19a391..97de5918cdf 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/MetaItemStack.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/MetaItemStack.java
@@ -3,6 +3,7 @@
 import com.earth2me.essentials.textreader.BookInput;
 import com.earth2me.essentials.textreader.BookPager;
 import com.earth2me.essentials.textreader.IText;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.earth2me.essentials.utils.MaterialUtil;
 import com.earth2me.essentials.utils.NumberUtil;
@@ -41,7 +42,6 @@
 import java.util.List;
 import java.util.Locale;
 import java.util.Map;
-import java.util.logging.Level;
 import java.util.regex.Pattern;
 
 public class MetaItemStack {
@@ -138,9 +138,7 @@ public boolean canSpawn(final IEssentials ess) {
             } catch (final NoSuchMethodError nsme) {
                 return true;
             } catch (final Throwable npe) {
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().log(Level.INFO, "Itemstack is invalid", npe);
-                }
+                DebugLogUtil.debugLog("Itemstack is invalid", npe);
                 return false;
             }
         }
@@ -158,9 +156,7 @@ public void parseStringMeta(final CommandSource sender, final boolean allowUnsaf
             try {
                 stack = ess.getServer().getUnsafe().modifyItemStack(stack, Joiner.on(' ').join(Arrays.asList(string).subList(fromArg, string.length)));
             } catch (final NullPointerException npe) {
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().log(Level.INFO, "Itemstack is invalid", npe);
-                }
+                DebugLogUtil.debugLog("Itemstack is invalid", npe);
             } catch (final NoSuchMethodError nsme) {
                 throw new TranslatableException(nsme, "noMetaJson");
             } catch (final Throwable throwable) {
@@ -176,9 +172,7 @@ public void parseStringMeta(final CommandSource sender, final boolean allowUnsaf
                 // modifyItemStack requires that the item namespaced key is prepended to the components for some reason
                 stack = ess.getServer().getUnsafe().modifyItemStack(stack, stack.getType().getKey() + components);
             } catch (final NullPointerException npe) {
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().log(Level.INFO, "Itemstack is invalid", npe);
-                }
+                DebugLogUtil.debugLog("Itemstack is invalid", npe);
             } catch (final Throwable throwable) {
                 throw new Exception(throwable.getMessage(), throwable);
             }
diff --git a/Essentials/src/main/java/com/earth2me/essentials/ProviderFactory.java b/Essentials/src/main/java/com/earth2me/essentials/ProviderFactory.java
index 8cf458a7404..726201289a0 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/ProviderFactory.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/ProviderFactory.java
@@ -1,5 +1,6 @@
 package com.earth2me.essentials;
 
+import com.earth2me.essentials.utils.DebugLogUtil;
 import io.papermc.lib.PaperLib;
 import net.ess3.provider.Provider;
 import net.essentialsx.providers.NullableProvider;
@@ -46,9 +47,7 @@ public final void registerProvider(final Class<? extends Provider>... toRegister
             if (Provider.class.isAssignableFrom(superclass)) {
                 //noinspection unchecked
                 registeredProviders.computeIfAbsent((Class<? extends Provider>) superclass, k -> new ArrayList<>()).add(provider);
-                if (essentials.getSettings().isDebug()) {
-                    essentials.getLogger().info("Registered provider " + provider.getSimpleName() + " for " + superclass.getSimpleName());
-                }
+                DebugLogUtil.debugLog("Registered provider " + provider.getSimpleName() + " for " + superclass.getSimpleName());
             }
         }
     }
diff --git a/Essentials/src/main/java/com/earth2me/essentials/Settings.java b/Essentials/src/main/java/com/earth2me/essentials/Settings.java
index 8980aa97b3f..b4e288716d9 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/Settings.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/Settings.java
@@ -9,6 +9,7 @@
 import com.earth2me.essentials.textreader.IText;
 import com.earth2me.essentials.textreader.SimpleTextInput;
 import com.earth2me.essentials.utils.AdventureUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.EnumUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.earth2me.essentials.utils.LocationUtil;
@@ -610,9 +611,7 @@ public String getChatFormat(final String group) {
     @Override
     public String getChatFormat(final String group, final ChatType chatType) {
         final String mFormat = chatFormats.getFormat(group, chatType, new ChatFormatConfigSupplier(group, chatType));
-        if (isDebug()) {
-            ess.getLogger().info(String.format("Found format '%s' for group '%s'", mFormat, group));
-        }
+        DebugLogUtil.debugLog(String.format("Found format '%s' for group '%s'", mFormat, group));
         return mFormat;
     }
 
@@ -824,9 +823,7 @@ public void reloadConfig() {
         if (knownCommandsProvider != null) {
             boolean mapModified = false;
             if (!disabledBukkitCommands.isEmpty()) {
-                if (isDebug()) {
-                    ess.getLogger().log(Level.INFO, "Re-adding " + disabledBukkitCommands.size() + " disabled commands!");
-                }
+                DebugLogUtil.debugLog("Re-adding " + disabledBukkitCommands.size() + " disabled commands!");
                 knownCommandsProvider.getKnownCommands().putAll(disabledBukkitCommands);
                 disabledBukkitCommands.clear();
                 mapModified = true;
@@ -848,14 +845,10 @@ public void reloadConfig() {
                 final String effectiveAlias = command.toLowerCase(Locale.ENGLISH);
                 final Command toDisable = ess.getPluginCommand(effectiveAlias);
                 if (toDisable != null) {
-                    if (isDebug()) {
-                        ess.getLogger().log(Level.INFO, "Attempting removal of " + effectiveAlias);
-                    }
+                    DebugLogUtil.debugLog("Attempting removal of " + effectiveAlias);
                     final Command removed = knownCommandsProvider.getKnownCommands().remove(effectiveAlias);
                     if (removed != null) {
-                        if (isDebug()) {
-                            ess.getLogger().log(Level.INFO, "Adding command " + effectiveAlias + " to disabled map!");
-                        }
+                        DebugLogUtil.debugLog("Adding command " + effectiveAlias + " to disabled map!");
                         disabledBukkitCommands.put(effectiveAlias, removed);
                     }
 
@@ -872,9 +865,7 @@ public void reloadConfig() {
             final SyncCommandsProvider syncCommandsProvider = ess.provider(SyncCommandsProvider.class);
 
             if (mapModified) {
-                if (isDebug()) {
-                    ess.getLogger().log(Level.INFO, "Syncing commands");
-                }
+                DebugLogUtil.debugLog("Syncing commands");
                 if (reloadCount.get() < 2) {
                     ess.scheduleSyncDelayedTask(syncCommandsProvider::syncCommands);
                 } else {
@@ -1804,9 +1795,7 @@ public Entry<Pattern, Long> getCommandCooldownEntry(final String label) {
             for (final Entry<Pattern, Long> entry : this.commandCooldowns.entrySet()) {
                 // Check if label matches current pattern (command-cooldown in config)
                 final boolean matches = entry.getKey().matcher(label).matches();
-                if (isDebug()) {
-                    ess.getLogger().info(String.format("Checking command '%s' against cooldown '%s': %s", label, entry.getKey(), matches));
-                }
+                DebugLogUtil.debugLog(String.format("Checking command '%s' against cooldown '%s': %s", label, entry.getKey(), matches));
 
                 if (matches) {
                     return entry;
diff --git a/Essentials/src/main/java/com/earth2me/essentials/Trade.java b/Essentials/src/main/java/com/earth2me/essentials/Trade.java
index 5168e2d76ca..121b71d881b 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/Trade.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/Trade.java
@@ -3,6 +3,7 @@
 import com.earth2me.essentials.craftbukkit.Inventories;
 import com.earth2me.essentials.craftbukkit.SetExpFix;
 import com.earth2me.essentials.utils.AdventureUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.NumberUtil;
 import com.earth2me.essentials.utils.VersionUtil;
 import net.ess3.api.IEssentials;
@@ -187,9 +188,7 @@ public void isAffordableFor(final IUser user) throws ChargeException {
     }
 
     public void isAffordableFor(final IUser user, final CompletableFuture<Boolean> future) {
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().log(Level.INFO, "checking if " + user.getName() + " can afford charge.");
-        }
+        DebugLogUtil.debugLog("checking if " + user.getName() + " can afford charge.");
 
         if (getMoney() != null && getMoney().signum() > 0 && !user.canAfford(getMoney())) {
             future.completeExceptionally(new ChargeException("notEnoughMoney", AdventureUtil.parsed(NumberUtil.displayCurrency(getMoney(), ess))));
@@ -218,16 +217,12 @@ public boolean pay(final IUser user) throws MaxMoneyException {
 
     public Map<Integer, ItemStack> pay(final IUser user, final OverflowType type) throws MaxMoneyException {
         if (getMoney() != null && getMoney().signum() > 0) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.INFO, "paying user " + user.getName() + " via trade " + getMoney().toPlainString());
-            }
+            DebugLogUtil.debugLog("paying user " + user.getName() + " via trade " + getMoney().toPlainString());
             user.giveMoney(getMoney());
         }
         if (getItemStack() != null) {
             if (type == OverflowType.ABORT && !Inventories.hasSpace(user.getBase(), 0, false, getItemStack())) {
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().log(Level.INFO, "abort paying " + user.getName() + " itemstack " + getItemStack().toString() + " due to lack of inventory space ");
-                }
+                DebugLogUtil.debugLog("abort paying " + user.getName() + " itemstack " + getItemStack().toString() + " due to lack of inventory space ");
                 return Collections.singletonMap(0, getItemStack());
             }
 
@@ -235,9 +230,7 @@ public Map<Integer, ItemStack> pay(final IUser user, final OverflowType type) th
             user.getBase().updateInventory();
             if (!leftover.isEmpty()) {
                 if (type == OverflowType.RETURN) {
-                    if (ess.getSettings().isDebug()) {
-                        ess.getLogger().log(Level.INFO, "paying " + user.getName() + " partial itemstack " + getItemStack().toString() + " with overflow " + leftover.get(0).toString());
-                    }
+                    DebugLogUtil.debugLog("paying " + user.getName() + " partial itemstack " + getItemStack().toString() + " with overflow " + leftover.get(0).toString());
                     return leftover;
                 } else {
                     for (final ItemStack itemStack : leftover.values()) {
@@ -248,12 +241,10 @@ public Map<Integer, ItemStack> pay(final IUser user, final OverflowType type) th
                             spillAmount -= itemStack.getAmount();
                         }
                     }
-                    if (ess.getSettings().isDebug()) {
-                        ess.getLogger().log(Level.INFO, "paying " + user.getName() + " partial itemstack " + getItemStack().toString() + " and dropping overflow " + leftover.get(0).toString());
-                    }
+                    DebugLogUtil.debugLog("paying " + user.getName() + " partial itemstack " + getItemStack().toString() + " and dropping overflow " + leftover.get(0).toString());
                 }
-            } else if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.INFO, "paying " + user.getName() + " itemstack " + getItemStack().toString());
+            } else {
+                DebugLogUtil.debugLog("paying " + user.getName() + " itemstack " + getItemStack().toString());
             }
             user.getBase().updateInventory();
         }
@@ -278,13 +269,9 @@ public void charge(final IUser user) throws ChargeException {
     }
 
     public void charge(final IUser user, final CompletableFuture<Boolean> future) {
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().log(Level.INFO, "attempting to charge user " + user.getName());
-        }
+        DebugLogUtil.debugLog("attempting to charge user " + user.getName());
         if (getMoney() != null) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.INFO, "charging user " + user.getName() + " money " + getMoney().toPlainString());
-            }
+            DebugLogUtil.debugLog("charging user " + user.getName() + " money " + getMoney().toPlainString());
             if (!user.canAfford(getMoney()) && getMoney().signum() > 0) {
                 future.completeExceptionally(new ChargeException("notEnoughMoney", AdventureUtil.parsed(NumberUtil.displayCurrency(getMoney(), ess))));
                 return;
@@ -292,9 +279,7 @@ public void charge(final IUser user, final CompletableFuture<Boolean> future) {
             user.takeMoney(getMoney());
         }
         if (getItemStack() != null) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.INFO, "charging user " + user.getName() + " itemstack " + getItemStack().toString());
-            }
+            DebugLogUtil.debugLog("charging user " + user.getName() + " itemstack " + getItemStack().toString());
             if (!Inventories.containsAtLeast(user.getBase(), getItemStack(), getItemStack().getAmount())) {
                 future.completeExceptionally(new ChargeException("missingItems", getItemStack().getAmount(), getItemStack().getType().toString().toLowerCase(Locale.ENGLISH).replace("_", " ")));
                 return;
@@ -311,9 +296,7 @@ public void charge(final IUser user, final CompletableFuture<Boolean> future) {
             user.takeMoney(cost);
         }
         if (getExperience() != null) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.INFO, "charging user " + user.getName() + " exp " + getExperience());
-            }
+            DebugLogUtil.debugLog("charging user " + user.getName() + " exp " + getExperience());
             final int experience = SetExpFix.getTotalExperience(user.getBase());
             if (experience < getExperience() && getExperience() > 0) {
                 future.completeExceptionally(new ChargeException("notEnoughExperience"));
@@ -321,9 +304,7 @@ public void charge(final IUser user, final CompletableFuture<Boolean> future) {
             }
             SetExpFix.setTotalExperience(user.getBase(), experience - getExperience());
         }
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().log(Level.INFO, "charge user " + user.getName() + " completed");
-        }
+        DebugLogUtil.debugLog("charge user " + user.getName() + " completed");
     }
 
     public BigDecimal getMoney() {
@@ -358,9 +339,7 @@ public BigDecimal getCommandCost(final IUser user) {
                 cost = fallbackTrade.getCommandCost(user);
             }
 
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.INFO, "calculated command (" + command + ") cost for " + user.getName() + " as " + cost);
-            }
+            DebugLogUtil.debugLog("calculated command (" + command + ") cost for " + user.getName() + " as " + cost);
         }
         if (cost.signum() != 0 && (user.isAuthorized("essentials.nocommandcost.all") || user.isAuthorized("essentials.nocommandcost." + command))) {
             return BigDecimal.ZERO;
diff --git a/Essentials/src/main/java/com/earth2me/essentials/User.java b/Essentials/src/main/java/com/earth2me/essentials/User.java
index 72f6feaad6c..fa86ca75382 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/User.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/User.java
@@ -8,6 +8,7 @@
 import com.earth2me.essentials.messaging.SimpleMessageRecipient;
 import com.earth2me.essentials.utils.AdventureUtil;
 import com.earth2me.essentials.utils.DateUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.EnumUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.earth2me.essentials.utils.NumberUtil;
@@ -137,18 +138,14 @@ public boolean isAuthorized(final IEssentialsCommand cmd, final String permissio
     @Override
     public boolean isAuthorized(final String node) {
         final boolean result = isAuthorizedCheck(node);
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().log(Level.INFO, "checking if " + base.getName() + " has " + node + " - " + result);
-        }
+        DebugLogUtil.debugLog("checking if " + base.getName() + " has " + node + " - " + result);
         return result;
     }
 
     @Override
     public boolean isPermissionSet(final String node) {
         final boolean result = isPermSetCheck(node);
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().log(Level.INFO, "checking if " + base.getName() + " has " + node + " (set-explicit) - " + result);
-        }
+        DebugLogUtil.debugLog("checking if " + base.getName() + " has " + node + " (set-explicit) - " + result);
         return result;
     }
 
@@ -168,11 +165,8 @@ private boolean isAuthorizedCheck(final String node) {
         try {
             return ess.getPermissionsHandler().hasPermission(base, node);
         } catch (final Exception ex) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.SEVERE, "Permission System Error: " + ess.getPermissionsHandler().getName() + " returned: " + ex.getMessage(), ex);
-            } else {
-                ess.getLogger().log(Level.SEVERE, "Permission System Error: " + ess.getPermissionsHandler().getName() + " returned: " + ex.getMessage());
-            }
+            DebugLogUtil.debugLog("Permission System Error: " + ess.getPermissionsHandler().getName() + " returned: " + ex.getMessage(), ex);
+            ess.getLogger().log(Level.SEVERE, "Permission System Error: " + ess.getPermissionsHandler().getName() + " returned: " + ex.getMessage());
 
             return false;
         }
@@ -186,11 +180,8 @@ private boolean isPermSetCheck(final String node) {
         try {
             return ess.getPermissionsHandler().isPermissionSet(base, node);
         } catch (final Exception ex) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.SEVERE, "Permission System Error: " + ess.getPermissionsHandler().getName() + " returned: " + ex.getMessage(), ex);
-            } else {
-                ess.getLogger().log(Level.SEVERE, "Permission System Error: " + ess.getPermissionsHandler().getName() + " returned: " + ex.getMessage());
-            }
+            DebugLogUtil.debugLog("Permission System Error: " + ess.getPermissionsHandler().getName() + " returned: " + ex.getMessage(), ex);
+            ess.getLogger().log(Level.SEVERE, "Permission System Error: " + ess.getPermissionsHandler().getName() + " returned: " + ex.getMessage());
 
             return false;
         }
@@ -204,11 +195,8 @@ private TriState isAuthorizedExactCheck(final String node) {
         try {
             return ess.getPermissionsHandler().isPermissionSetExact(base, node);
         } catch (final Exception ex) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.SEVERE, "Permission System Error: " + ess.getPermissionsHandler().getName() + " returned: " + ex.getMessage(), ex);
-            } else {
-                ess.getLogger().log(Level.SEVERE, "Permission System Error: " + ess.getPermissionsHandler().getName() + " returned: " + ex.getMessage());
-            }
+            DebugLogUtil.debugLog("Permission System Error: " + ess.getPermissionsHandler().getName() + " returned: " + ex.getMessage(), ex);
+            ess.getLogger().log(Level.SEVERE, "Permission System Error: " + ess.getPermissionsHandler().getName() + " returned: " + ex.getMessage());
 
             return TriState.UNSET;
         }
@@ -528,9 +516,7 @@ public void setDisplayNick() {
                 try {
                     this.getBase().setPlayerListName(name);
                 } catch (final IllegalArgumentException e) {
-                    if (ess.getSettings().isDebug()) {
-                        ess.getLogger().log(Level.INFO, "Playerlist for " + name + " was not updated. Name clashed with another online player.");
-                    }
+                    DebugLogUtil.debugLog("Playerlist for " + name + " was not updated. Name clashed with another online player.");
                 }
             }
         }
@@ -582,9 +568,7 @@ public void setMoney(final BigDecimal value) throws MaxMoneyException {
 
     private BigDecimal _getMoney() {
         if (ess.getSettings().isEcoDisabled()) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().info("Internal economy functions disabled, aborting balance check.");
-            }
+            DebugLogUtil.debugLog("Internal economy functions disabled, aborting balance check.");
             return BigDecimal.ZERO;
         }
         final EconomyLayer layer = EconomyLayers.getSelectedLayer();
@@ -596,9 +580,7 @@ private BigDecimal _getMoney() {
 
     public void setMoney(final BigDecimal value, final UserBalanceUpdateEvent.Cause cause) throws MaxMoneyException {
         if (ess.getSettings().isEcoDisabled()) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().info("Internal economy functions disabled, aborting balance change.");
-            }
+            DebugLogUtil.debugLog("Internal economy functions disabled, aborting balance change.");
             return;
         }
         final BigDecimal oldBalance = _getMoney();
@@ -882,18 +864,14 @@ public boolean isGodModeEnabledRaw() {
     @Override
     public String getGroup() {
         final String result = ess.getPermissionsHandler().getGroup(base);
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().log(Level.INFO, "looking up groupname of " + base.getName() + " - " + result);
-        }
+        DebugLogUtil.debugLog("looking up groupname of " + base.getName() + " - " + result);
         return result;
     }
 
     @Override
     public boolean inGroup(final String group) {
         final boolean result = ess.getPermissionsHandler().inGroup(base, group);
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().log(Level.INFO, "checking if " + base.getName() + " is in group " + group + " - " + result);
-        }
+        DebugLogUtil.debugLog("checking if " + base.getName() + " is in group " + group + " - " + result);
         return result;
     }
 
diff --git a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandbalancetop.java b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandbalancetop.java
index f5915467fdc..efeee5d2e75 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandbalancetop.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandbalancetop.java
@@ -5,6 +5,7 @@
 import com.earth2me.essentials.textreader.SimpleTextInput;
 import com.earth2me.essentials.textreader.TextPager;
 import com.earth2me.essentials.utils.AdventureUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.EnumUtil;
 import com.earth2me.essentials.utils.NumberUtil;
 import com.earth2me.essentials.utils.VersionUtil;
@@ -104,9 +105,7 @@ private class Viewer implements Runnable {
         @Override
         public void run() {
             if (ess.getSettings().isEcoDisabled()) {
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().info("Internal economy functions disabled, aborting baltop.");
-                }
+                DebugLogUtil.debugLog("Internal economy functions disabled, aborting baltop.");
                 return;
             }
 
diff --git a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandcreatekit.java b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandcreatekit.java
index 7325a75b770..f78a82200e1 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandcreatekit.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandcreatekit.java
@@ -4,6 +4,7 @@
 import com.earth2me.essentials.User;
 import com.earth2me.essentials.craftbukkit.Inventories;
 import com.earth2me.essentials.utils.DateUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.PasteUtil;
 import net.ess3.api.TranslatableException;
 import net.ess3.provider.SerializationProvider;
@@ -94,9 +95,7 @@ private void uploadPaste(final CommandSource sender, final String kitName, final
                         sender.sendMessage(separator);
                         sender.sendTl("createKitSuccess", kitName, delayFormat, result.getPasteUrl());
                         sender.sendMessage(separator);
-                        if (ess.getSettings().isDebug()) {
-                            ess.getLogger().info(sender.getSender().getName() + " created a kit: " + result.getPasteUrl());
-                        }
+                        DebugLogUtil.debugLog(sender.getSender().getName() + " created a kit: " + result.getPasteUrl());
                     }
                 });
                 future.exceptionally(throwable -> {
diff --git a/Essentials/src/main/java/com/earth2me/essentials/commands/Commanddelhome.java b/Essentials/src/main/java/com/earth2me/essentials/commands/Commanddelhome.java
index 20500ef45d2..7b14b817e17 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/commands/Commanddelhome.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/commands/Commanddelhome.java
@@ -3,6 +3,7 @@
 import com.earth2me.essentials.CommandSource;
 import com.earth2me.essentials.IUser;
 import com.earth2me.essentials.User;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import net.ess3.api.TranslatableException;
 import net.essentialsx.api.v2.events.HomeModifyEvent;
 import org.bukkit.Bukkit;
@@ -22,9 +23,7 @@ private void deleteHome(CommandSource sender, User user, String home) {
         final HomeModifyEvent event = new HomeModifyEvent(sender.getUser(), user, home, user.getHome(home), false);
         Bukkit.getServer().getPluginManager().callEvent(event);
         if (event.isCancelled()) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().info("HomeModifyEvent canceled for /delhome execution by " + sender.getDisplayName());
-            }
+            DebugLogUtil.debugLog("HomeModifyEvent canceled for /delhome execution by " + sender.getDisplayName());
             return;
         }
 
diff --git a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandeditsign.java b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandeditsign.java
index b6908bdae56..493f8e0fd0f 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandeditsign.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandeditsign.java
@@ -1,6 +1,7 @@
 package com.earth2me.essentials.commands;
 
 import com.earth2me.essentials.User;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.earth2me.essentials.utils.NumberUtil;
 import com.earth2me.essentials.utils.VersionUtil;
@@ -133,9 +134,7 @@ private boolean callSignEvent(final ModifiableSign sign, final Player player, fi
 
         Bukkit.getServer().getPluginManager().callEvent(event);
         if (event.isCancelled()) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().info("SignChangeEvent canceled for /editsign execution by " + player.getName());
-            }
+            DebugLogUtil.debugLog("SignChangeEvent canceled for /editsign execution by " + player.getName());
             return true;
         }
 
diff --git a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandessentials.java b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandessentials.java
index fa97ff2ff9f..25f12d2fee8 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandessentials.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandessentials.java
@@ -10,6 +10,7 @@
 import com.earth2me.essentials.utils.AdventureUtil;
 import com.earth2me.essentials.utils.CommandMapUtil;
 import com.earth2me.essentials.utils.DateUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.FloatUtil;
 import com.earth2me.essentials.utils.NumberUtil;
 import com.earth2me.essentials.utils.PasteUtil;
@@ -578,9 +579,7 @@ private void runCleanup(final Server server, final CommandSource sender, final S
                     continue;
                 }
 
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().info("Deleting user: " + user.getName() + " Money: " + moneyCount + " Homes: " + homeCount + " Last seen: " + DateUtil.formatDateDiff(lastLog));
-                }
+                DebugLogUtil.debugLog("Deleting user: " + user.getName() + " Money: " + moneyCount + " Homes: " + homeCount + " Last seen: " + DateUtil.formatDateDiff(lastLog));
 
                 user.reset();
             }
diff --git a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandkit.java b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandkit.java
index 1394a3c5e86..48c862756cd 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandkit.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandkit.java
@@ -4,6 +4,7 @@
 import com.earth2me.essentials.Kit;
 import com.earth2me.essentials.User;
 import com.earth2me.essentials.utils.AdventureUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.StringUtil;
 import net.ess3.api.TranslatableException;
 import org.bukkit.Server;
@@ -12,7 +13,6 @@
 import java.util.Collections;
 import java.util.List;
 import java.util.Locale;
-import java.util.logging.Level;
 
 public class Commandkit extends EssentialsCommand {
     public Commandkit() {
@@ -86,9 +86,7 @@ private void giveKits(final User userTo, final User userFrom, final String kitNa
                 userTo.sendTl("kitReceive", kit.getName());
 
             } catch (final NoChargeException ex) {
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().log(Level.INFO, "Soft kit error, abort spawning " + kit.getName(), ex);
-                }
+                DebugLogUtil.debugLog("Soft kit error, abort spawning " + kit.getName(), ex);
             } catch (final Exception ex) {
                 ess.showError(userFrom.getSource(), ex, "\\ kit: " + kit.getName());
             }
diff --git a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandrenamehome.java b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandrenamehome.java
index 4bf8e3cbc45..e343da59a08 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandrenamehome.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandrenamehome.java
@@ -2,6 +2,7 @@
 
 import com.earth2me.essentials.CommandSource;
 import com.earth2me.essentials.User;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.NumberUtil;
 import net.ess3.api.IUser;
 import net.ess3.api.TranslatableException;
@@ -64,9 +65,7 @@ public void run(final Server server, final User user, final String commandLabel,
         final HomeModifyEvent event = new HomeModifyEvent(user, usersHome, oldName, newName, usersHome.getHome(oldName));
         Bukkit.getServer().getPluginManager().callEvent(event);
         if (event.isCancelled()) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().info("HomeModifyEvent canceled for /renamehome execution by " + user.getDisplayName());
-            }
+            DebugLogUtil.debugLog("HomeModifyEvent canceled for /renamehome execution by " + user.getDisplayName());
             return;
         }
 
diff --git a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandsethome.java b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandsethome.java
index a3f446bdd80..7358a914974 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandsethome.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandsethome.java
@@ -2,6 +2,7 @@
 
 import com.earth2me.essentials.CommandSource;
 import com.earth2me.essentials.User;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.LocationUtil;
 import com.earth2me.essentials.utils.NumberUtil;
 import net.ess3.api.TranslatableException;
@@ -74,9 +75,7 @@ public void run(final Server server, final User user, final String commandLabel,
 
         Bukkit.getServer().getPluginManager().callEvent(event);
         if (event.isCancelled()) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().info("HomeModifyEvent canceled for /sethome execution by " + user.getDisplayName());
-            }
+            DebugLogUtil.debugLog("HomeModifyEvent canceled for /sethome execution by " + user.getDisplayName());
             return;
         }
 
diff --git a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandtpaccept.java b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandtpaccept.java
index 43398bdb799..1e6239a6da0 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandtpaccept.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandtpaccept.java
@@ -4,6 +4,7 @@
 import com.earth2me.essentials.IUser;
 import com.earth2me.essentials.Trade;
 import com.earth2me.essentials.User;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import net.ess3.api.TranslatableException;
 import net.essentialsx.api.v2.events.TeleportRequestResponseEvent;
 import org.bukkit.Bukkit;
@@ -97,9 +98,7 @@ private void handleTeleport(final User user, final IUser.TpaRequest request, Str
         final TeleportRequestResponseEvent event = new TeleportRequestResponseEvent(user, requester, request, true);
         Bukkit.getPluginManager().callEvent(event);
         if (event.isCancelled()) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().info("TPA accept cancelled by API for " + user.getName() + " (requested by " + requester.getName() + ")");
-            }
+            DebugLogUtil.debugLog("TPA accept cancelled by API for " + user.getName() + " (requested by " + requester.getName() + ")");
             return;
         }
 
diff --git a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandtpdeny.java b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandtpdeny.java
index 869eb7da20c..eb3e336fab4 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/commands/Commandtpdeny.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/commands/Commandtpdeny.java
@@ -2,6 +2,7 @@
 
 import com.earth2me.essentials.IUser;
 import com.earth2me.essentials.User;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import net.ess3.api.TranslatableException;
 import net.essentialsx.api.v2.events.TeleportRequestResponseEvent;
 import org.bukkit.Bukkit;
@@ -82,8 +83,8 @@ private boolean sendEvent(User user, User player, IUser.TpaRequest request) {
         final TeleportRequestResponseEvent event = new TeleportRequestResponseEvent(user, player, request, false);
         Bukkit.getPluginManager().callEvent(event);
         final boolean cancelled = event.isCancelled();
-        if (cancelled && ess.getSettings().isDebug()) {
-            ess.getLogger().info("TPA deny cancelled by API for " + user.getName() + " (requested by " + player.getName() + ")");
+        if (cancelled) {
+            DebugLogUtil.debugLog("TPA deny cancelled by API for " + user.getName() + " (requested by " + player.getName() + ")");
         }
         return event.isCancelled();
     }
diff --git a/Essentials/src/main/java/com/earth2me/essentials/commands/EssentialsCommand.java b/Essentials/src/main/java/com/earth2me/essentials/commands/EssentialsCommand.java
index 897c3d98101..22baa88640b 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/commands/EssentialsCommand.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/commands/EssentialsCommand.java
@@ -5,6 +5,7 @@
 import com.earth2me.essentials.IEssentialsModule;
 import com.earth2me.essentials.Trade;
 import com.earth2me.essentials.User;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.google.common.collect.ImmutableList;
 import com.google.common.collect.Lists;
@@ -314,17 +315,13 @@ protected final List<String> tabCompleteCommand(final CommandSource sender, fina
         }
 
         final int numArgs = args.length - index - 1;
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().info(numArgs + " " + index + " " + Arrays.toString(args));
-        }
+        DebugLogUtil.debugLog(numArgs + " " + index + " " + Arrays.toString(args));
         String[] effectiveArgs = new String[numArgs];
         System.arraycopy(args, index, effectiveArgs, 0, numArgs);
         if (effectiveArgs.length == 0) {
             effectiveArgs = new String[] {""};
         }
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().info(command + " -- " + Arrays.toString(effectiveArgs));
-        }
+        DebugLogUtil.debugLog(command + " -- " + Arrays.toString(effectiveArgs));
 
         return command.tabComplete(sender.getSender(), label, effectiveArgs);
     }
diff --git a/Essentials/src/main/java/com/earth2me/essentials/economy/vault/VaultEconomyProvider.java b/Essentials/src/main/java/com/earth2me/essentials/economy/vault/VaultEconomyProvider.java
index 091c9a2f320..5e8b2a3f165 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/economy/vault/VaultEconomyProvider.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/economy/vault/VaultEconomyProvider.java
@@ -6,6 +6,7 @@
 import com.earth2me.essentials.api.UserDoesNotExistException;
 import com.earth2me.essentials.config.EssentialsUserConfiguration;
 import com.earth2me.essentials.utils.AdventureUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.NumberUtil;
 import com.earth2me.essentials.utils.StringUtil;
 import com.google.common.base.Charsets;
@@ -318,9 +319,7 @@ public boolean createPlayerAccount(OfflinePlayer player) {
         }
 
         // Loading a v4 UUID that we somehow didn't track, mark it as a normal player and hope for the best, vault sucks :/
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().info("Vault requested a player account creation for a v4 UUID: " + player);
-        }
+        DebugLogUtil.debugLog("Vault requested a player account creation for a v4 UUID: " + player);
 
         final Player userPlayer;
         if (player instanceof Player) {
diff --git a/Essentials/src/main/java/com/earth2me/essentials/items/AbstractItemDb.java b/Essentials/src/main/java/com/earth2me/essentials/items/AbstractItemDb.java
index a3bcd932fdc..b212eac6c3b 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/items/AbstractItemDb.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/items/AbstractItemDb.java
@@ -4,6 +4,7 @@
 import com.earth2me.essentials.IConf;
 import com.earth2me.essentials.User;
 import com.earth2me.essentials.craftbukkit.Inventories;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.earth2me.essentials.utils.MaterialUtil;
 import com.earth2me.essentials.utils.VersionUtil;
@@ -104,9 +105,7 @@ public ItemStack get(final String id) throws Exception {
 
     ItemStack tryResolverDeserialize(final String id) {
         for (final PluginKey key : resolverMap.keySet()) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().info(String.format("Trying to deserialize item '%s' with resolver '%s'...", id, key));
-            }
+            DebugLogUtil.debugLog(String.format("Trying to deserialize item '%s' with resolver '%s'...", id, key));
 
             final Function<String, ItemStack> resolver = resolverMap.get(key);
             final ItemStack stack = resolver.apply(id);
@@ -121,9 +120,7 @@ ItemStack tryResolverDeserialize(final String id) {
 
     String tryResolverSerialize(final ItemStack stack) {
         for (final PluginKey key : resolverMap.keySet()) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().info(String.format("Trying to serialize '%s' with resolver '%s'...", stack.toString(), key));
-            }
+            DebugLogUtil.debugLog(String.format("Trying to serialize '%s' with resolver '%s'...", stack.toString(), key));
 
             final ItemResolver resolver = resolverMap.get(key);
             final String serialized = resolver.serialize(stack);
diff --git a/Essentials/src/main/java/com/earth2me/essentials/signs/EssentialsSign.java b/Essentials/src/main/java/com/earth2me/essentials/signs/EssentialsSign.java
index 7e6e1bc3cd0..8e1405628ea 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/signs/EssentialsSign.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/signs/EssentialsSign.java
@@ -6,6 +6,7 @@
 import com.earth2me.essentials.Trade;
 import com.earth2me.essentials.User;
 import com.earth2me.essentials.utils.AdventureUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.earth2me.essentials.utils.MaterialUtil;
 import com.earth2me.essentials.utils.NumberUtil;
@@ -111,9 +112,7 @@ protected final boolean onSignCreate(final SignChangeEvent event, final IEssenti
         final SignCreateEvent signEvent = new SignCreateEvent(sign, this, user);
         ess.getServer().getPluginManager().callEvent(signEvent);
         if (signEvent.isCancelled()) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().info("SignCreateEvent cancelled for sign " + signEvent.getEssentialsSign().getName());
-            }
+            DebugLogUtil.debugLog("SignCreateEvent cancelled for sign " + signEvent.getEssentialsSign().getName());
             return false;
         }
 
diff --git a/Essentials/src/main/java/com/earth2me/essentials/signs/SignBlockListener.java b/Essentials/src/main/java/com/earth2me/essentials/signs/SignBlockListener.java
index 39966f3784f..7034d64ca5a 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/signs/SignBlockListener.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/signs/SignBlockListener.java
@@ -1,6 +1,7 @@
 package com.earth2me.essentials.signs;
 
 import com.earth2me.essentials.User;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.earth2me.essentials.utils.MaterialUtil;
 import net.ess3.api.IEssentials;
@@ -48,9 +49,7 @@ public void onSignBlockBreak(final BlockBreakEvent event) {
     public boolean protectSignsAndBlocks(final Block block, final Player player) throws MaxMoneyException {
         // prevent any signs be broken by destroying the block they are attached to
         if (EssentialsSign.checkIfBlockBreaksSigns(block)) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.INFO, "Prevented that a block was broken next to a sign.");
-            }
+            DebugLogUtil.debugLog("Prevented that a block was broken next to a sign.");
             return true;
         }
 
diff --git a/Essentials/src/main/java/com/earth2me/essentials/signs/SignPlayerListener.java b/Essentials/src/main/java/com/earth2me/essentials/signs/SignPlayerListener.java
index ff2638c7d3f..63432154ae0 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/signs/SignPlayerListener.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/signs/SignPlayerListener.java
@@ -1,5 +1,6 @@
 package com.earth2me.essentials.signs;
 
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.MaterialUtil;
 import net.ess3.api.IEssentials;
 import org.bukkit.Material;
@@ -11,8 +12,6 @@
 import org.bukkit.event.block.Action;
 import org.bukkit.event.player.PlayerInteractEvent;
 
-import java.util.logging.Level;
-
 public class SignPlayerListener implements Listener {
     private final transient IEssentials ess;
 
@@ -39,9 +38,7 @@ public void onSignPlayerInteract(final PlayerInteractEvent event) {
             try {
                 targetBlock = ess.getUser(event.getPlayer()).getTargetBlock(5);
             } catch (final IllegalStateException ex) {
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().log(Level.WARNING, ex.getMessage(), ex);
-                }
+                DebugLogUtil.debugLog(ex.getMessage(), ex);
             }
             block = targetBlock;
         } else {
diff --git a/Essentials/src/main/java/com/earth2me/essentials/textreader/KeywordReplacer.java b/Essentials/src/main/java/com/earth2me/essentials/textreader/KeywordReplacer.java
index e61c5ced543..6d364ab6121 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/textreader/KeywordReplacer.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/textreader/KeywordReplacer.java
@@ -6,6 +6,7 @@
 import com.earth2me.essentials.User;
 import com.earth2me.essentials.utils.AdventureUtil;
 import com.earth2me.essentials.utils.DateUtil;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.DescParseTickFormat;
 import com.earth2me.essentials.utils.EnumUtil;
 import com.earth2me.essentials.utils.FormatUtil;
@@ -27,7 +28,6 @@
 import java.util.List;
 import java.util.Locale;
 import java.util.Map;
-import java.util.logging.Level;
 import java.util.regex.Matcher;
 import java.util.regex.Pattern;
 
@@ -159,9 +159,7 @@ private void replaceKeywords(final CommandSource sender) {
 
         execTimer.mark("Text Replace");
         final String timeroutput = execTimer.end();
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().log(Level.INFO, "Keyword Replacer " + timeroutput);
-        }
+        DebugLogUtil.debugLog("Keyword Replacer " + timeroutput);
     }
 
     private String replaceLine(String line, final String fullMatch, final String[] matchTokens, final User user) {
diff --git a/Essentials/src/main/java/com/earth2me/essentials/userstorage/ModernUUIDCache.java b/Essentials/src/main/java/com/earth2me/essentials/userstorage/ModernUUIDCache.java
index 8c0a88bbd9b..f30ebe0d172 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/userstorage/ModernUUIDCache.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/userstorage/ModernUUIDCache.java
@@ -1,5 +1,6 @@
 package com.earth2me.essentials.userstorage;
 
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.StringUtil;
 import com.google.common.io.Files;
 import net.ess3.api.IEssentials;
@@ -93,9 +94,7 @@ protected void updateCache(final UUID uuid, final String name) {
             final String sanitizedName = getSanitizedName(name);
             final UUID replacedUuid = nameToUuidMap.put(sanitizedName, uuid);
             if (!uuid.equals(replacedUuid)) {
-                if (ess.getSettings().isDebug()) {
-                    ess.getLogger().log(Level.WARNING, "Replaced UUID during cache update for " + sanitizedName + ": " + replacedUuid + " -> " + uuid);
-                }
+                DebugLogUtil.debugLog("Replaced UUID during cache update for " + sanitizedName + ": " + replacedUuid + " -> " + uuid);
                 pendingNameWrite.set(true);
             }
         }
@@ -127,8 +126,6 @@ protected void removeCache(final UUID uuid) {
     }
 
     private void loadCache() {
-        final boolean debug = ess.getSettings().isDebug();
-
         try {
             if (!nameToUuidFile.exists()) {
                 if (!nameToUuidFile.createNewFile()) {
@@ -137,9 +134,7 @@ private void loadCache() {
                 return;
             }
 
-            if (debug) {
-                ess.getLogger().log(Level.INFO, "Loading Name->UUID cache from disk...");
-            }
+            DebugLogUtil.debugLog("Loading Name->UUID cache from disk...");
 
             nameToUuidMap.clear();
 
@@ -148,8 +143,8 @@ private void loadCache() {
                     final String username = dis.readUTF();
                     final UUID uuid = new UUID(dis.readLong(), dis.readLong());
                     final UUID previous = nameToUuidMap.put(username, uuid);
-                    if (previous != null && debug) {
-                        ess.getLogger().log(Level.WARNING, "Replaced UUID during cache load for " + username + ": " + previous + " -> " + uuid);
+                    if (previous != null) {
+                        DebugLogUtil.debugLog("Replaced UUID during cache load for " + username + ": " + previous + " -> " + uuid);
                     }
                 }
             }
@@ -165,17 +160,15 @@ private void loadCache() {
                 return;
             }
 
-            if (debug) {
-                ess.getLogger().log(Level.INFO, "Loading UUID cache from disk...");
-            }
+            DebugLogUtil.debugLog("Loading UUID cache from disk...");
 
             uuidCache.clear();
 
             try (final DataInputStream dis = new DataInputStream(new FileInputStream(uuidCacheFile))) {
                 while (dis.available() > 0) {
                     final UUID uuid = new UUID(dis.readLong(), dis.readLong());
-                    if (uuidCache.contains(uuid) && debug) {
-                        ess.getLogger().log(Level.WARNING, "UUID " + uuid + " duplicated in cache");
+                    if (uuidCache.contains(uuid)) {
+                        DebugLogUtil.debugLog("UUID " + uuid + " duplicated in cache");
                     }
                     uuidCache.add(uuid);
                 }
@@ -186,9 +179,7 @@ private void loadCache() {
     }
 
     private void saveUuidCache() {
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().log(Level.INFO, "Saving UUID cache to disk...");
-        }
+        DebugLogUtil.debugLog("Saving UUID cache to disk...");
 
         try {
             final File tmpMap = File.createTempFile("uuids", ".tmp.bin", ess.getDataFolder());
@@ -202,9 +193,7 @@ private void saveUuidCache() {
     }
 
     private void saveNameToUuidCache() {
-        if (ess.getSettings().isDebug()) {
-            ess.getLogger().log(Level.INFO, "Saving Name->UUID cache to disk...");
-        }
+        DebugLogUtil.debugLog("Saving Name->UUID cache to disk...");
 
         try {
             final File tmpMap = File.createTempFile("usermap", ".tmp.bin", ess.getDataFolder());
diff --git a/Essentials/src/main/java/com/earth2me/essentials/userstorage/ModernUserMap.java b/Essentials/src/main/java/com/earth2me/essentials/userstorage/ModernUserMap.java
index 6c9351c0d06..8443f9aae3f 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/userstorage/ModernUserMap.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/userstorage/ModernUserMap.java
@@ -2,6 +2,7 @@
 
 import com.earth2me.essentials.OfflinePlayerStub;
 import com.earth2me.essentials.User;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.NumberUtil;
 import com.google.common.cache.CacheBuilder;
 import com.google.common.cache.CacheLoader;
@@ -76,9 +77,7 @@ public User getUser(final UUID uuid) {
         try {
             return userCache.get(uuid);
         } catch (ExecutionException e) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.WARNING, "Exception while getting user for " + uuid, e);
-            }
+            DebugLogUtil.debugLog("Exception while getting user for " + uuid, e);
             return null;
         }
     }
@@ -139,9 +138,7 @@ public User loadUncachedUser(final Player base) {
             debugLogUncachedNonPlayer(base);
             user = new User(base, ess);
         } else if (!base.equals(user.getBase())) {
-            if (ess.getSettings().isDebug()) {
-                ess.getLogger().log(Level.INFO, "Essentials updated the underlying Player object for " + user.getUUID());
-            }
+            DebugLogUtil.debugLog("Essentials updated the underlying Player object for " + user.getUUID());
             user.update(base);
         }
         uuidCache.updateCache(user.getUUID(), user.getName());
diff --git a/Essentials/src/main/java/com/earth2me/essentials/utils/DebugLogUtil.java b/Essentials/src/main/java/com/earth2me/essentials/utils/DebugLogUtil.java
new file mode 100644
index 00000000000..af3d27bf1b7
--- /dev/null
+++ b/Essentials/src/main/java/com/earth2me/essentials/utils/DebugLogUtil.java
@@ -0,0 +1,83 @@
+package com.earth2me.essentials.utils;
+
+import com.earth2me.essentials.Essentials;
+import org.apache.logging.log4j.Level;
+import org.apache.logging.log4j.LogManager;
+import org.apache.logging.log4j.core.Appender;
+import org.apache.logging.log4j.core.LoggerContext;
+import org.apache.logging.log4j.core.config.Configuration;
+import org.apache.logging.log4j.core.impl.Log4jLogEvent;
+import org.apache.logging.log4j.message.SimpleMessage;
+
+public abstract class DebugLogUtil {
+    private static Essentials essentials;
+    private static final DebugLogUtil INSTANCE;
+
+    static {
+        if (Essentials.TESTING) {
+            INSTANCE = new DebugLogUtil() {
+                @Override
+                protected void debugLogInternal(String message, Throwable throwable) {
+                    essentials.getLogger().log(java.util.logging.Level.INFO, message, throwable);
+                }
+            };
+        } else {
+            INSTANCE = new DebugLogUtilImpl();
+        }
+    }
+
+    private static final class DebugLogUtilImpl extends DebugLogUtil {
+        private final Appender APPENDER;
+
+        private DebugLogUtilImpl() {
+            final LoggerContext ctx = (LoggerContext) LogManager.getContext(false);
+            final Configuration cfg = ctx.getConfiguration();
+
+            // if this ever breaks, we can do cfg.getAppenders() and look for instanceof RollingRandomAccessFileAppender
+            APPENDER = cfg.getAppender("File");
+
+            if (APPENDER == null) {
+                System.out.println("Unable to find latest.log appender. Please report this to the EssX team!");
+            }
+        }
+
+        @Override
+        protected void debugLogInternal(String message, Throwable throwable) {
+            if (APPENDER == null && essentials == null) {
+                System.out.println(message);
+                return;
+            }
+
+            if (APPENDER == null || essentials != null && essentials.getSettings().isDebug()) {
+                essentials.getLogger().log(java.util.logging.Level.INFO, message);
+                return;
+            }
+
+            final Log4jLogEvent evt = Log4jLogEvent.newBuilder()
+                    .setLoggerName("EssentialsDebug")
+                    .setLevel(Level.INFO)
+                    .setMessage(new SimpleMessage(message))
+                    .setThrown(throwable)
+                    .build();
+            APPENDER.append(evt);
+        }
+    }
+
+    private DebugLogUtil() {
+    }
+
+    public static void setEssentials(Essentials essentials) {
+        DebugLogUtil.essentials = essentials;
+    }
+
+    public static void debugLog(final String message) {
+        debugLog(message, null);
+    }
+
+    protected abstract void debugLogInternal(final String message, final Throwable throwable);
+
+    public static void debugLog(final String message, final Throwable throwable) {
+        INSTANCE.debugLogInternal(message, throwable);
+    }
+
+}
diff --git a/EssentialsAntiBuild/src/main/java/com/earth2me/essentials/antibuild/EssentialsAntiBuildListener.java b/EssentialsAntiBuild/src/main/java/com/earth2me/essentials/antibuild/EssentialsAntiBuildListener.java
index 6949ded7dda..e0e47b571e2 100644
--- a/EssentialsAntiBuild/src/main/java/com/earth2me/essentials/antibuild/EssentialsAntiBuildListener.java
+++ b/EssentialsAntiBuild/src/main/java/com/earth2me/essentials/antibuild/EssentialsAntiBuildListener.java
@@ -1,6 +1,7 @@
 package com.earth2me.essentials.antibuild;
 
 import com.earth2me.essentials.User;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.EnumUtil;
 import com.earth2me.essentials.utils.VersionUtil;
 import net.ess3.api.IEssentials;
@@ -33,8 +34,6 @@
 import org.bukkit.event.player.PlayerPickupItemEvent;
 import org.bukkit.inventory.ItemStack;
 
-import java.util.logging.Level;
-
 public class EssentialsAntiBuildListener implements Listener {
     final private transient IAntiBuild prot;
     final private transient IEssentials ess;
@@ -61,9 +60,7 @@ private static boolean isEntityPickupEvent() {
 
     private boolean metaPermCheck(final User user, final String action, final Block block) {
         if (block == null) {
-            if (ess.getSettings().isDebug()) {
-                prot.getLogger().log(Level.INFO, "AntiBuild permission check failed, invalid block.");
-            }
+            DebugLogUtil.debugLog("AntiBuild permission check failed, invalid block.");
             return false;
         }
         if (VersionUtil.PRE_FLATTENING) {
@@ -74,9 +71,7 @@ private boolean metaPermCheck(final User user, final String action, final Block
 
     private boolean metaPermCheck(final User user, final String action, final ItemStack item) {
         if (item == null) {
-            if (ess.getSettings().isDebug()) {
-                prot.getLogger().log(Level.INFO, "AntiBuild permission check failed, invalid item.");
-            }
+            DebugLogUtil.debugLog("AntiBuild permission check failed, invalid item.");
             return false;
         }
         if (VersionUtil.PRE_FLATTENING) {
@@ -98,9 +93,7 @@ private boolean metaPermCheck(final User user, final String action, final Materi
             if (user.getBase().isPermissionSet(dataPerm)) {
                 return user.isAuthorized(dataPerm);
             } else {
-                if (ess.getSettings().isDebug()) {
-                    prot.getLogger().log(Level.INFO, "DataValue perm on " + user.getName() + " is not directly set: " + dataPerm);
-                }
+                DebugLogUtil.debugLog("DataValue perm on " + user.getName() + " is not directly set: " + dataPerm);
             }
         }
 
diff --git a/EssentialsDiscord/src/main/java/net/essentialsx/discord/JDADiscordService.java b/EssentialsDiscord/src/main/java/net/essentialsx/discord/JDADiscordService.java
index 96a8300a9a0..176fe5872fd 100644
--- a/EssentialsDiscord/src/main/java/net/essentialsx/discord/JDADiscordService.java
+++ b/EssentialsDiscord/src/main/java/net/essentialsx/discord/JDADiscordService.java
@@ -5,6 +5,7 @@
 import club.minnced.discord.webhook.send.WebhookMessageBuilder;
 import com.earth2me.essentials.IEssentialsModule;
 import com.earth2me.essentials.User;
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.earth2me.essentials.utils.NumberUtil;
 import com.earth2me.essentials.utils.VersionUtil;
@@ -108,14 +109,10 @@ public TextChannel getChannel(String key, boolean primaryFallback) {
     public TextChannel getDefinedChannel(String key, boolean primaryFallback) {
         final long resolvedId = getSettings().getChannelId(key);
 
-        if (isDebug()) {
-            logger.log(Level.INFO, "Channel definition " + key + " resolved as " + resolvedId);
-        }
+        DebugLogUtil.debugLog("Channel definition " + key + " resolved as " + resolvedId);
         TextChannel channel = guild.getTextChannelById(resolvedId);
         if (channel == null && primaryFallback) {
-            if (isDebug()) {
-                logger.log(Level.WARNING, "Resolved channel id " + resolvedId + " was not found! Falling back to primary channel.");
-            }
+            DebugLogUtil.debugLog("Resolved channel id " + resolvedId + " was not found! Falling back to primary channel.");
             channel = primaryChannel;
         }
         return channel;
diff --git a/EssentialsDiscord/src/main/java/net/essentialsx/discord/interactions/InteractionControllerImpl.java b/EssentialsDiscord/src/main/java/net/essentialsx/discord/interactions/InteractionControllerImpl.java
index 26581597214..b9462121fc9 100644
--- a/EssentialsDiscord/src/main/java/net/essentialsx/discord/interactions/InteractionControllerImpl.java
+++ b/EssentialsDiscord/src/main/java/net/essentialsx/discord/interactions/InteractionControllerImpl.java
@@ -1,5 +1,6 @@
 package net.essentialsx.discord.interactions;
 
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.StringUtil;
 import net.dv8tion.jda.api.events.interaction.command.SlashCommandInteractionEvent;
 import net.dv8tion.jda.api.exceptions.ErrorResponseException;
@@ -94,16 +95,12 @@ public void processBatchRegistration() {
                 for (final Command command : success) {
                     commandMap.put(command.getName(), batchRegistrationQueue.get(command.getName()));
                     batchRegistrationQueue.remove(command.getName());
-                    if (jda.isDebug()) {
-                        logger.info("Registered guild command " + command.getName() + " with id " + command.getId());
-                    }
+                    DebugLogUtil.debugLog("Registered guild command " + command.getName() + " with id " + command.getId());
                 }
 
                 if (!batchRegistrationQueue.isEmpty()) {
                     logger.warning(batchRegistrationQueue.size() + " Discord commands were lost during command registration!");
-                    if (jda.isDebug()) {
-                        logger.warning("Lost commands: " + batchRegistrationQueue.keySet());
-                    }
+                    DebugLogUtil.debugLog("Lost commands: " + batchRegistrationQueue.keySet());
                     batchRegistrationQueue.clear();
                 }
             }, failure -> {
@@ -127,9 +124,7 @@ public void registerCommand(InteractionCommand command) throws InteractionExcept
         }
 
         if (!initialBatchRegistration) {
-            if (jda.isDebug()) {
-                logger.info("Marked guild command for batch registration: " + command.getName());
-            }
+            DebugLogUtil.debugLog("Marked guild command for batch registration: " + command.getName());
             batchRegistrationQueue.put(command.getName(), command);
             return;
         }
@@ -143,9 +138,7 @@ public void registerCommand(InteractionCommand command) throws InteractionExcept
 
         jda.getGuild().upsertCommand(data).queue(success -> {
             commandMap.put(command.getName(), command);
-            if (jda.isDebug()) {
-                logger.info("Registered guild command " + success.getName() + " with id " + success.getId());
-            }
+            DebugLogUtil.debugLog("Registered guild command " + success.getName() + " with id " + success.getId());
         }, failure -> {
             if (failure instanceof ErrorResponseException && ((ErrorResponseException) failure).getErrorResponse() == ErrorResponse.MISSING_ACCESS) {
                 logger.severe(tlLiteral("discordErrorCommand"));
diff --git a/EssentialsDiscord/src/main/java/net/essentialsx/discord/listeners/DiscordListener.java b/EssentialsDiscord/src/main/java/net/essentialsx/discord/listeners/DiscordListener.java
index ea2b0ddb34b..188d4797143 100644
--- a/EssentialsDiscord/src/main/java/net/essentialsx/discord/listeners/DiscordListener.java
+++ b/EssentialsDiscord/src/main/java/net/essentialsx/discord/listeners/DiscordListener.java
@@ -1,5 +1,6 @@
 package net.essentialsx.discord.listeners;
 
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.earth2me.essentials.utils.StringUtil;
 import com.vdurmont.emoji.EmojiParser;
@@ -23,7 +24,6 @@
 import java.util.ArrayList;
 import java.util.Collections;
 import java.util.List;
-import java.util.logging.Level;
 import java.util.logging.Logger;
 import java.util.regex.Pattern;
 
@@ -53,9 +53,7 @@ public void onMessageReceived(@NotNull MessageReceivedEvent event) {
         // Get list of channel names that have this channel id mapped
         final List<String> keys = plugin.getPlugin().getSettings().getKeysFromChannelId(event.getChannel().getIdLong());
         if (keys == null || keys.size() == 0) {
-            if (plugin.isDebug()) {
-                logger.log(Level.INFO, "Skipping message due to no channel keys for id " + event.getChannel().getIdLong() + "!");
-            }
+            DebugLogUtil.debugLog("Skipping message due to no channel keys for id " + event.getChannel().getIdLong() + "!");
             return;
         }
 
@@ -67,9 +65,7 @@ public void onMessageReceived(@NotNull MessageReceivedEvent event) {
         if (!plugin.getSettings().getDiscordFilters().isEmpty()) {
             for (final Pattern pattern : plugin.getSettings().getDiscordFilters()) {
                 if (pattern.matcher(message.getContentDisplay()).find()) {
-                    if (plugin.isDebug()) {
-                        logger.log(Level.INFO, "Skipping message " + message.getId() + " with content, \"" + message.getContentDisplay() + "\" as it matched the filter!");
-                    }
+                    DebugLogUtil.debugLog("Skipping message " + message.getId() + " with content, \"" + message.getContentDisplay() + "\" as it matched the filter!");
                     return;
                 }
             }
@@ -93,10 +89,8 @@ public void onMessageReceived(@NotNull MessageReceivedEvent event) {
                 FormatUtil.replaceFormat(strippedMessage) : FormatUtil.stripFormat(strippedMessage);
 
         // Don't send blank messages
-        if (finalMessage.trim().length() == 0) {
-            if (plugin.isDebug()) {
-                logger.log(Level.INFO, "Skipping finalized empty message " + message.getId());
-            }
+        if (finalMessage.trim().isEmpty()) {
+            DebugLogUtil.debugLog("Skipping finalized empty message " + message.getId());
             return;
         }
 
diff --git a/EssentialsDiscord/src/main/java/net/essentialsx/discord/util/ConsoleInjector.java b/EssentialsDiscord/src/main/java/net/essentialsx/discord/util/ConsoleInjector.java
index 52ea96c64a8..2c8f23e3b16 100644
--- a/EssentialsDiscord/src/main/java/net/essentialsx/discord/util/ConsoleInjector.java
+++ b/EssentialsDiscord/src/main/java/net/essentialsx/discord/util/ConsoleInjector.java
@@ -1,5 +1,6 @@
 package net.essentialsx.discord.util;
 
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.earth2me.essentials.utils.FormatUtil;
 import com.google.common.base.Splitter;
 import net.dv8tion.jda.api.entities.Message;
@@ -55,9 +56,7 @@ public ConsoleInjector(JDADiscordService jda) {
                 }
 
                 final int backoff = recentRateLimit.incrementAndGet();
-                if (jda.isDebug()) {
-                    logger.warning("EssXBackoff: Webhook backoff in progress, skipping queue processing. Resuming in " + Math.abs(backoff) + " cycles.");
-                }
+                DebugLogUtil.debugLog("EssXBackoff: Webhook backoff in progress, skipping queue processing. Resuming in " + Math.abs(backoff) + " cycles.");
                 return;
             }
 
@@ -115,10 +114,8 @@ public void append(LogEvent event) {
                 }
             } else if (recentRateLimit.get() >= 2) {
                 // Start the webhook backoff, defaulting to 20s, which should reset our bucket.
-                if (jda.isDebug()) {
-                    totalBackoffEvents.getAndIncrement();
-                    logger.warning("EssXBackoff: Beginning Webhook Backoff");
-                }
+                totalBackoffEvents.getAndIncrement();
+                DebugLogUtil.debugLog("EssXBackoff: Beginning Webhook Backoff");
                 recentRateLimit.set(-20);
             }
             return;
diff --git a/EssentialsDiscordLink/src/main/java/net/essentialsx/discordlink/AccountStorage.java b/EssentialsDiscordLink/src/main/java/net/essentialsx/discordlink/AccountStorage.java
index f7d95b582be..c43840c7bc0 100644
--- a/EssentialsDiscordLink/src/main/java/net/essentialsx/discordlink/AccountStorage.java
+++ b/EssentialsDiscordLink/src/main/java/net/essentialsx/discordlink/AccountStorage.java
@@ -1,5 +1,6 @@
 package net.essentialsx.discordlink;
 
+import com.earth2me.essentials.utils.DebugLogUtil;
 import com.google.common.collect.BiMap;
 import com.google.common.collect.HashBiMap;
 import com.google.common.collect.Maps;
@@ -48,9 +49,7 @@ public AccountStorage(final EssentialsDiscordLink plugin) throws IOException {
                 return;
             }
 
-            if (plugin.getEss().getSettings().isDebug()) {
-                plugin.getLogger().log(Level.INFO, "Saving linked discord accounts to disk...");
-            }
+            DebugLogUtil.debugLog("Saving linked discord accounts to disk...");
 
             final Map<String, String> clone;
             clone = new HashMap<>(uuidToDiscordIdMap);