diff --git a/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/Request.java b/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/Request.java
index 230e1f1fa..a0e3f1dee 100644
--- a/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/Request.java
+++ b/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/Request.java
@@ -116,4 +116,15 @@ public final class Request {
     public Request omitFirstInPath() {
         return new Request(method, path.omitFirst(), query, user, headers);
     }
+
+    @Override
+    public String toString() {
+        return "Request{" +
+                "method='" + method + '\'' +
+                ", path=" + path +
+                ", query=" + query +
+                ", user=" + user +
+                ", headers=" + headers +
+                '}';
+    }
 }
\ No newline at end of file
diff --git a/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/URIPath.java b/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/URIPath.java
index 6144b1576..2f251cfcb 100644
--- a/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/URIPath.java
+++ b/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/URIPath.java
@@ -119,4 +119,11 @@ public final class URIPath {
         }
         return count;
     }
+
+    @Override
+    public String toString() {
+        return "URIPath{" +
+                "path='" + path + '\'' +
+                '}';
+    }
 }
diff --git a/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/URIQuery.java b/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/URIQuery.java
index 9b9f72dde..e50c22d73 100644
--- a/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/URIQuery.java
+++ b/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/URIQuery.java
@@ -94,4 +94,11 @@ public final class URIQuery {
         }
         return builder.toString();
     }
+
+    @Override
+    public String toString() {
+        return "URIQuery{" +
+                "byKey=" + byKey +
+                '}';
+    }
 }
diff --git a/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/WebUser.java b/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/WebUser.java
index 35ac7f128..ccaaa7eb2 100644
--- a/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/WebUser.java
+++ b/Plan/api/src/main/java/com/djrapitops/plan/delivery/web/resolver/request/WebUser.java
@@ -59,4 +59,13 @@ public final class WebUser {
     public String getUsername() {
         return username;
     }
+
+    @Override
+    public String toString() {
+        return "WebUser{" +
+                "playerName='" + playerName + '\'' +
+                ", username='" + username + '\'' +
+                ", permissions=" + permissions +
+                '}';
+    }
 }
diff --git a/Plan/bukkit/src/main/java/com/djrapitops/plan/addons/placeholderapi/PlanPlaceholderExtension.java b/Plan/bukkit/src/main/java/com/djrapitops/plan/addons/placeholderapi/PlanPlaceholderExtension.java
index 1ac11cf2a..47ad69a73 100644
--- a/Plan/bukkit/src/main/java/com/djrapitops/plan/addons/placeholderapi/PlanPlaceholderExtension.java
+++ b/Plan/bukkit/src/main/java/com/djrapitops/plan/addons/placeholderapi/PlanPlaceholderExtension.java
@@ -18,6 +18,7 @@ package com.djrapitops.plan.addons.placeholderapi;
 
 import com.djrapitops.plan.PlanSystem;
 import com.djrapitops.plan.placeholder.PlanPlaceholders;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plan.version.VersionChecker;
 import com.djrapitops.plugin.logging.L;
@@ -92,7 +93,7 @@ public class PlanPlaceholderExtension extends PlaceholderExpansion {
 
             return value;
         } catch (Exception e) {
-            errorLogger.log(L.WARN, getClass(), e);
+            errorLogger.log(L.WARN, e, ErrorContext.builder().whatToDo("Report this").related("Placeholder Request", params).build());
             return null;
         }
     }
diff --git a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/BukkitAFKListener.java b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/BukkitAFKListener.java
index f8214bd24..153d368da 100644
--- a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/BukkitAFKListener.java
+++ b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/BukkitAFKListener.java
@@ -19,6 +19,7 @@ package com.djrapitops.plan.gathering.listeners.bukkit;
 import com.djrapitops.plan.gathering.afk.AFKTracker;
 import com.djrapitops.plan.settings.Permissions;
 import com.djrapitops.plan.settings.config.PlanConfig;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import org.bukkit.entity.Player;
@@ -79,7 +80,7 @@ public class BukkitAFKListener implements Listener {
 
             AFK_TRACKER.performedAction(uuid, time);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
diff --git a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/ChatListener.java b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/ChatListener.java
index 61e4b6b30..abf47aad7 100644
--- a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/ChatListener.java
+++ b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/ChatListener.java
@@ -21,6 +21,7 @@ import com.djrapitops.plan.gathering.cache.NicknameCache;
 import com.djrapitops.plan.identification.ServerInfo;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.transactions.events.NicknameStoreTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import org.bukkit.entity.Player;
@@ -66,7 +67,7 @@ public class ChatListener implements Listener {
         try {
             actOnChatEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
diff --git a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/DeathEventListener.java b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/DeathEventListener.java
index 336f0c9c5..d1b886e01 100644
--- a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/DeathEventListener.java
+++ b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/DeathEventListener.java
@@ -23,6 +23,7 @@ import com.djrapitops.plan.gathering.domain.Session;
 import com.djrapitops.plan.processing.Processing;
 import com.djrapitops.plan.processing.processors.player.MobKillProcessor;
 import com.djrapitops.plan.processing.processors.player.PlayerKillProcessor;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import org.bukkit.Material;
@@ -80,7 +81,7 @@ public class DeathEventListener implements Listener {
             UUID uuid = dead instanceof Player ? dead.getUniqueId() : null;
             handleKill(time, uuid, killerEntity);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event, dead).build());
         }
     }
 
diff --git a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/GameModeChangeListener.java b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/GameModeChangeListener.java
index 6837159de..b99888bb2 100644
--- a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/GameModeChangeListener.java
+++ b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/GameModeChangeListener.java
@@ -22,6 +22,7 @@ import com.djrapitops.plan.identification.ServerInfo;
 import com.djrapitops.plan.settings.config.WorldAliasSettings;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.transactions.events.WorldNameStoreTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import org.bukkit.entity.Player;
@@ -67,7 +68,7 @@ public class GameModeChangeListener implements Listener {
         try {
             actOnEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event, event.getPlayer().getGameMode() + "->" + event.getNewGameMode()).build());
         }
     }
 
diff --git a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/PlayerOnlineListener.java b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/PlayerOnlineListener.java
index 9d07061da..1c9777539 100644
--- a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/PlayerOnlineListener.java
+++ b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/PlayerOnlineListener.java
@@ -36,6 +36,7 @@ import com.djrapitops.plan.settings.config.paths.ExportSettings;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.Database;
 import com.djrapitops.plan.storage.database.transactions.events.*;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import org.bukkit.entity.Player;
@@ -107,7 +108,7 @@ public class PlayerOnlineListener implements Listener {
             dbSystem.getDatabase().executeTransaction(new BanStatusTransaction(playerUUID, () -> banned));
             dbSystem.getDatabase().executeTransaction(new OperatorStatusTransaction(playerUUID, operator));
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event, event.getResult()).build());
         }
     }
 
@@ -132,7 +133,7 @@ public class PlayerOnlineListener implements Listener {
 
             dbSystem.getDatabase().executeTransaction(new KickStoreTransaction(uuid));
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
@@ -141,7 +142,7 @@ public class PlayerOnlineListener implements Listener {
         try {
             actOnJoinEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
@@ -205,7 +206,7 @@ public class PlayerOnlineListener implements Listener {
         try {
             actOnQuitEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
diff --git a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/WorldChangeListener.java b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/WorldChangeListener.java
index a384ffeb5..f6529993e 100644
--- a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/WorldChangeListener.java
+++ b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/listeners/bukkit/WorldChangeListener.java
@@ -22,6 +22,7 @@ import com.djrapitops.plan.identification.ServerInfo;
 import com.djrapitops.plan.settings.config.WorldAliasSettings;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.transactions.events.WorldNameStoreTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import org.bukkit.entity.Player;
@@ -59,7 +60,7 @@ public class WorldChangeListener implements Listener {
         try {
             actOnEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
diff --git a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/timed/BukkitPingCounter.java b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/timed/BukkitPingCounter.java
index 93de12942..68429589a 100644
--- a/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/timed/BukkitPingCounter.java
+++ b/Plan/bukkit/src/main/java/com/djrapitops/plan/gathering/timed/BukkitPingCounter.java
@@ -89,8 +89,7 @@ public class BukkitPingCounter extends AbsRunnable implements Listener {
             } catch (NoSuchMethodException | IllegalAccessException | NoSuchFieldException reflectiveEx) {
                 Logger.getGlobal().log(
                         Level.WARNING,
-                        "Plan: Reflective exception in static initializer of PingCountTimer",
-                        reflectiveEx
+                        "Plan: Could not register Ping counter due to " + reflectiveEx
                 );
             } catch (IllegalArgumentException e) {
                 Logger.getGlobal().log(
diff --git a/Plan/bungeecord/src/main/java/com/djrapitops/plan/gathering/listeners/bungee/PlayerOnlineListener.java b/Plan/bungeecord/src/main/java/com/djrapitops/plan/gathering/listeners/bungee/PlayerOnlineListener.java
index 15e98c5ed..5d0df3b05 100644
--- a/Plan/bungeecord/src/main/java/com/djrapitops/plan/gathering/listeners/bungee/PlayerOnlineListener.java
+++ b/Plan/bungeecord/src/main/java/com/djrapitops/plan/gathering/listeners/bungee/PlayerOnlineListener.java
@@ -34,6 +34,7 @@ import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.Database;
 import com.djrapitops.plan.storage.database.transactions.events.GeoInfoStoreTransaction;
 import com.djrapitops.plan.storage.database.transactions.events.PlayerRegisterTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import net.md_5.bungee.api.connection.ProxiedPlayer;
@@ -92,7 +93,7 @@ public class PlayerOnlineListener implements Listener {
         try {
             actOnLogin(event);
         } catch (Exception e) {
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
@@ -142,7 +143,7 @@ public class PlayerOnlineListener implements Listener {
         try {
             actOnLogout(event);
         } catch (Exception e) {
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
@@ -179,7 +180,7 @@ public class PlayerOnlineListener implements Listener {
         try {
             actOnServerSwitch(event);
         } catch (Exception e) {
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/PlanSystem.java b/Plan/common/src/main/java/com/djrapitops/plan/PlanSystem.java
index f3fa4bf31..74969fb30 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/PlanSystem.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/PlanSystem.java
@@ -37,6 +37,7 @@ import com.djrapitops.plan.settings.SettingsSvc;
 import com.djrapitops.plan.settings.locale.LocaleSystem;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.file.PlanFiles;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plan.version.VersionChecker;
 import com.djrapitops.plugin.benchmarking.Benchmark;
@@ -222,7 +223,7 @@ public class PlanSystem implements SubSystem {
                     system.disable();
                 }
             } catch (Exception e) {
-                errorLogger.log(L.WARN, this.getClass(), e);
+                errorLogger.log(L.WARN, e, ErrorContext.builder().related("Disabling PlanSystem: " + system).build());
             }
         }
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/delivery/export/ExportScheduler.java b/Plan/common/src/main/java/com/djrapitops/plan/delivery/export/ExportScheduler.java
index b89073477..3457f8d61 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/delivery/export/ExportScheduler.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/delivery/export/ExportScheduler.java
@@ -73,7 +73,7 @@ public class ExportScheduler {
     private void schedulePlayersPageExport() {
         long period = TimeAmount.toTicks(config.get(ExportSettings.EXPORT_PERIOD), TimeUnit.MILLISECONDS);
         taskSystem.registerTask("Players page export",
-                new ExportTask(exporter, Exporter::exportPlayersPage, logger, errorLogger)
+                new ExportTask(exporter, Exporter::exportPlayersPage, errorLogger)
         ).runTaskTimerAsynchronously(0L, period);
     }
 
@@ -89,7 +89,7 @@ public class ExportScheduler {
 
         Optional<Server> proxy = servers.stream().filter(Server::isProxy).findFirst();
         proxy.ifPresent(mainServer -> taskSystem.registerTask("Network export",
-                new ExportTask(exporter, exporter -> exporter.exportServerPage(mainServer), logger, errorLogger))
+                new ExportTask(exporter, exporter -> exporter.exportServerPage(mainServer), errorLogger))
                 .runTaskTimerAsynchronously(0L, period)
         );
 
@@ -99,7 +99,7 @@ public class ExportScheduler {
                     new ExportTask(exporter, same -> {
                         same.exportServerPage(server);
                         same.exportServerJSON(server);
-                    }, logger, errorLogger))
+                    }, errorLogger))
                     .runTaskTimerAsynchronously(offset * offsetMultiplier, period);
             offsetMultiplier++;
         }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/delivery/export/ExportTask.java b/Plan/common/src/main/java/com/djrapitops/plan/delivery/export/ExportTask.java
index dae6e2f90..47c769d36 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/delivery/export/ExportTask.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/delivery/export/ExportTask.java
@@ -19,27 +19,24 @@ package com.djrapitops.plan.delivery.export;
 import com.djrapitops.plan.exceptions.ExportException;
 import com.djrapitops.plan.exceptions.database.DBOpException;
 import com.djrapitops.plan.utilities.java.ThrowingConsumer;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
-import com.djrapitops.plugin.logging.console.PluginLogger;
 import com.djrapitops.plugin.task.AbsRunnable;
 
 public class ExportTask extends AbsRunnable {
 
     private final Exporter exporter;
     private final ThrowingConsumer<Exporter, ExportException> exportAction;
-    private final PluginLogger logger;
     private final ErrorLogger errorLogger;
 
     public ExportTask(
             Exporter exporter,
             ThrowingConsumer<Exporter, ExportException> exportAction,
-            PluginLogger logger,
             ErrorLogger errorLogger
     ) {
         this.exporter = exporter;
         this.exportAction = exportAction;
-        this.logger = logger;
         this.errorLogger = errorLogger;
     }
 
@@ -48,22 +45,26 @@ public class ExportTask extends AbsRunnable {
         try {
             exportAction.accept(exporter);
         } catch (ExportException e) {
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.WARN, e, ErrorContext.builder().related("Export task run").build());
         } catch (DBOpException dbException) {
             handleDBException(dbException);
         } catch (Exception | NoClassDefFoundError | NoSuchMethodError | NoSuchFieldError e) {
-            logger.error("Export Task Disabled due to error, reload Plan to re-enable.");
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder()
+                    .whatToDo("Export Task Disabled due to error - reload Plan to re-enable.")
+                    .related("Export task run").build());
             cancel();
         }
     }
 
     private void handleDBException(DBOpException dbException) {
-        logger.error("Export Task Disabled due to database error, reload Plan to re-enable.");
         if (dbException.getMessage().contains("closed")) {
-            logger.warn("(Error was caused by database closing, so this error can possibly be ignored.)");
+            errorLogger.log(L.ERROR, dbException, ErrorContext.builder()
+                    .whatToDo("Export Task Disabled due to error - database is closing, so this error can be ignored.).")
+                    .related("Export task run").build());
         } else {
-            errorLogger.log(L.ERROR, this.getClass(), dbException);
+            errorLogger.log(L.ERROR, dbException, ErrorContext.builder()
+                    .whatToDo("Export Task Disabled due to error - reload Plan to re-enable.")
+                    .related("Export task run").build());
         }
         cancel();
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/delivery/rendering/pages/DebugPage.java b/Plan/common/src/main/java/com/djrapitops/plan/delivery/rendering/pages/DebugPage.java
index ebfae5866..5bcad8459 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/delivery/rendering/pages/DebugPage.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/delivery/rendering/pages/DebugPage.java
@@ -31,6 +31,7 @@ import com.djrapitops.plan.identification.ServerInfo;
 import com.djrapitops.plan.identification.properties.ServerProperties;
 import com.djrapitops.plan.storage.database.Database;
 import com.djrapitops.plan.storage.file.ResourceCache;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plan.version.VersionChecker;
 import com.djrapitops.plugin.benchmarking.Benchmark;
@@ -135,7 +136,7 @@ public class DebugPage implements Page {
             }
             content.append("</pre>");
         } catch (Exception e) {
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.WARN, e, ErrorContext.builder().related("/debug page access, resource cache").build());
         }
     }
 
@@ -151,7 +152,7 @@ public class DebugPage implements Page {
             }
             content.append("</pre>");
         } catch (Exception e) {
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.WARN, e, ErrorContext.builder().related("/debug page access, JSON cache").build());
         }
     }
 
@@ -172,7 +173,7 @@ public class DebugPage implements Page {
             }
             content.append("</pre>");
         } catch (Exception e) {
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.WARN, e, ErrorContext.builder().related("/debug page access, Session cache").build());
         }
     }
 
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/delivery/web/ResourceSvc.java b/Plan/common/src/main/java/com/djrapitops/plan/delivery/web/ResourceSvc.java
index f95a45f93..9d7e4b3f7 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/delivery/web/ResourceSvc.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/delivery/web/ResourceSvc.java
@@ -23,6 +23,7 @@ import com.djrapitops.plan.settings.locale.Locale;
 import com.djrapitops.plan.settings.locale.lang.PluginLang;
 import com.djrapitops.plan.storage.file.PlanFiles;
 import com.djrapitops.plan.storage.file.Resource;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -145,7 +146,9 @@ public class ResourceSvc implements ResourceService {
                 return getOrWriteCustomized(fileName, source);
             }
         } catch (IOException e) {
-            errorLogger.log(L.WARN, getClass(), e.getCause());
+            errorLogger.log(L.WARN, e, ErrorContext.builder()
+                    .whatToDo("Report this or provide " + fileName + " in " + files.getCustomizationDirectory())
+                    .related("Fetching resource", "Of: " + pluginName, fileName).build());
         }
         // Return original by default
         return source.get();
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/NonProxyWebserverDisableChecker.java b/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/NonProxyWebserverDisableChecker.java
index dc8e38bc2..4986d9c63 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/NonProxyWebserverDisableChecker.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/NonProxyWebserverDisableChecker.java
@@ -19,6 +19,7 @@ package com.djrapitops.plan.delivery.webserver;
 import com.djrapitops.plan.settings.config.PlanConfig;
 import com.djrapitops.plan.settings.config.paths.PluginSettings;
 import com.djrapitops.plan.settings.config.paths.WebserverSettings;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -73,9 +74,10 @@ public class NonProxyWebserverDisableChecker implements Runnable {
             config.set(WebserverSettings.DISABLED, true);
             config.save();
             logger.warn("Note: Set '" + WebserverSettings.DISABLED.getPath() + "' to true");
-
         } catch (IOException e) {
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.WARN, e, ErrorContext.builder()
+                    .whatToDo("Set '" + WebserverSettings.DISABLED.getPath() + "' to true manually.")
+                    .related("Disabling webserver in config setting", WebserverSettings.DISABLED.getPath()).build());
         }
     }
 }
\ No newline at end of file
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/RequestHandler.java b/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/RequestHandler.java
index 9b1de573b..e11a867b6 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/RequestHandler.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/RequestHandler.java
@@ -31,6 +31,7 @@ import com.djrapitops.plan.settings.config.PlanConfig;
 import com.djrapitops.plan.settings.config.paths.PluginSettings;
 import com.djrapitops.plan.settings.config.paths.WebserverSettings;
 import com.djrapitops.plan.storage.database.DBSystem;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -99,7 +100,10 @@ public class RequestHandler implements HttpHandler {
         } catch (Exception e) {
             if (config.isTrue(PluginSettings.DEV_MODE)) {
                 logger.warn("THIS ERROR IS ONLY LOGGED IN DEV MODE:");
-                errorLogger.log(L.WARN, this.getClass(), e);
+                errorLogger.log(L.WARN, e, ErrorContext.builder()
+                        .whatToDo("THIS ERROR IS ONLY LOGGED IN DEV MODE")
+                        .related(exchange.getRequestMethod(), exchange.getRemoteAddress(), exchange.getRequestHeaders(), exchange.getResponseHeaders(), exchange.getRequestURI())
+                        .build());
             }
         } finally {
             exchange.close();
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/ResponseResolver.java b/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/ResponseResolver.java
index 6172329e6..4b502c38e 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/ResponseResolver.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/ResponseResolver.java
@@ -31,6 +31,7 @@ import com.djrapitops.plan.delivery.webserver.resolver.auth.*;
 import com.djrapitops.plan.delivery.webserver.resolver.json.RootJSONResolver;
 import com.djrapitops.plan.exceptions.WebUserAuthException;
 import com.djrapitops.plan.exceptions.connection.ForbiddenException;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import dagger.Lazy;
@@ -143,7 +144,7 @@ public class ResponseResolver {
         } catch (WebUserAuthException e) {
             throw e; // Pass along
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(request).build());
             return responseFactory.internalErrorResponse(e, request.getPath().asString());
         }
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/WebServer.java b/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/WebServer.java
index 44e2674b6..c39e76c78 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/WebServer.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/delivery/webserver/WebServer.java
@@ -23,6 +23,7 @@ import com.djrapitops.plan.settings.config.paths.WebserverSettings;
 import com.djrapitops.plan.settings.locale.Locale;
 import com.djrapitops.plan.settings.locale.lang.PluginLang;
 import com.djrapitops.plan.storage.file.PlanFiles;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -145,7 +146,9 @@ public class WebServer implements SubSystem {
                             .namingPattern("Plan WebServer Thread-%d")
                             .uncaughtExceptionHandler((thread, throwable) -> {
                                 if (config.isTrue(PluginSettings.DEV_MODE)) {
-                                    errorLogger.log(L.WARN, WebServer.class, throwable);
+                                    errorLogger.log(L.WARN, throwable, ErrorContext.builder()
+                                            .whatToDo("THIS ERROR IS ONLY LOGGED IN DEV MODE")
+                                            .build());
                                 }
                             }).build()
             );
@@ -165,7 +168,7 @@ public class WebServer implements SubSystem {
             logger.error("Webserver failed to bind port: " + failedToBind.toString());
             enabled = false;
         } catch (IllegalArgumentException | IllegalStateException | IOException e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related("Trying to enable webserver", config.get(WebserverSettings.INTERNAL_IP) + ":" + port).build());
             enabled = false;
         }
     }
@@ -183,7 +186,9 @@ public class WebServer implements SubSystem {
             }
         } catch (InvalidPathException e) {
             logger.error("WebServer: Could not find Keystore: " + e.getMessage());
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder()
+                    .whatToDo(e.getMessage() + ", Fix this path to point to a valid keystore file: " + keyStorePath)
+                    .related(keyStorePath).build());
         }
 
         char[] storepass = config.get(WebserverSettings.CERTIFICATE_STOREPASS).toCharArray();
@@ -232,7 +237,7 @@ public class WebServer implements SubSystem {
             logger.error(e.getMessage());
         } catch (KeyManagementException | NoSuchAlgorithmException e) {
             logger.error(locale.getString(PluginLang.WEB_SERVER_FAIL_SSL_CONTEXT));
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(keyStoreKind).build());
         } catch (EOFException e) {
             logger.error(locale.getString(PluginLang.WEB_SERVER_FAIL_EMPTY_FILE));
         } catch (FileNotFoundException e) {
@@ -241,11 +246,12 @@ public class WebServer implements SubSystem {
         } catch (BindException e) {
             throw e; // Pass to above error handler
         } catch (IOException e) {
-            logger.error("WebServer: " + e);
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(config.get(WebserverSettings.INTERNAL_IP) + ":" + port).build());
         } catch (KeyStoreException | CertificateException | UnrecoverableKeyException e) {
             logger.error(locale.getString(PluginLang.WEB_SERVER_FAIL_STORE_LOAD));
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder()
+                    .whatToDo("Make sure the Certificate settings are correct / You can try remaking the keystore without -passin or -passout parameters.")
+                    .related(keyStorePath).build());
         }
         return startSuccessful;
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/exceptions/ExceptionWithContext.java b/Plan/common/src/main/java/com/djrapitops/plan/exceptions/ExceptionWithContext.java
new file mode 100644
index 000000000..f389e89dd
--- /dev/null
+++ b/Plan/common/src/main/java/com/djrapitops/plan/exceptions/ExceptionWithContext.java
@@ -0,0 +1,25 @@
+/*
+ *  This file is part of Player Analytics (Plan).
+ *
+ *  Plan is free software: you can redistribute it and/or modify
+ *  it under the terms of the GNU Lesser General Public License v3 as published by
+ *  the Free Software Foundation, either version 3 of the License, or
+ *  (at your option) any later version.
+ *
+ *  Plan is distributed in the hope that it will be useful,
+ *  but WITHOUT ANY WARRANTY; without even the implied warranty of
+ *  MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ *  GNU Lesser General Public License for more details.
+ *
+ *  You should have received a copy of the GNU Lesser General Public License
+ *  along with Plan. If not, see <https://www.gnu.org/licenses/>.
+ */
+package com.djrapitops.plan.exceptions;
+
+import com.djrapitops.plan.utilities.logging.ErrorContext;
+
+import java.util.Optional;
+
+public interface ExceptionWithContext {
+    Optional<ErrorContext> getContext();
+}
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/exceptions/database/DBOpException.java b/Plan/common/src/main/java/com/djrapitops/plan/exceptions/database/DBOpException.java
index 05159056d..4f3149d97 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/exceptions/database/DBOpException.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/exceptions/database/DBOpException.java
@@ -16,14 +16,20 @@
  */
 package com.djrapitops.plan.exceptions.database;
 
+import com.djrapitops.plan.exceptions.ExceptionWithContext;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
+
 import java.sql.SQLException;
+import java.util.Optional;
 
 /**
  * Runtime exception for wrapping database errors.
  *
  * @author Rsl1122
  */
-public class DBOpException extends IllegalStateException {
+public class DBOpException extends IllegalStateException implements ExceptionWithContext {
+
+    private ErrorContext context;
 
     public DBOpException(String message) {
         super(message);
@@ -33,8 +39,100 @@ public class DBOpException extends IllegalStateException {
         super(message, cause);
     }
 
-    public static DBOpException forCause(String sql, SQLException e) {
-        return new DBOpException("SQL Failed: " + sql + "; " + e.getMessage(), e);
+    public DBOpException(String message, Throwable cause, ErrorContext context) {
+        super(message, cause);
+        this.context = context;
     }
 
+    // Checkstyle.OFF: CyclomaticComplexity
+
+    public static DBOpException forCause(String sql, SQLException e) {
+        ErrorContext.Builder context = ErrorContext.builder();
+        int errorCode = e.getErrorCode();
+        context.related("Error code: " + errorCode)
+                .related(sql);
+        switch (errorCode) {
+            // SQLite Corrupt
+            case 10:
+            case 523:
+                context.related("SQL Corrupted")
+                        .whatToDo("Your SQLite has corrupted. This can happen if .db-wal or .db-shm files get replaced mid operation. Restore database.db from backup.");
+                break;
+            // Syntax error codes
+            case 1054: // MySQL
+            case 1064:
+            case 1146:
+            case 42000: // H2
+            case 42001:
+            case 42101:
+            case 42102:
+            case 42111:
+            case 42112:
+            case 42121:
+            case 42122:
+            case 42132:
+                context.related("SQL Grammar error")
+                        .whatToDo("Report this, there is an SQL grammar error.");
+                break;
+            // Type mismatch
+            case 20: // SQLite
+                context.related("SQL Type mismatch")
+                        .whatToDo("Report this, there is an SQL Type mismatch.");
+                break;
+            // Duplicate key
+            case 1062:
+            case 23001:
+            case 23505:
+                context.related("Duplicate key")
+                        .whatToDo("Report this, duplicate key exists in SQL.");
+                break;
+            // Constraint violation
+            case 19: // SQLite
+            case 275:
+            case 531:
+            case 787:
+            case 1043:
+            case 1299:
+            case 1555:
+            case 2579:
+            case 1811:
+            case 2067:
+            case 2323:
+            case 630: // MySQL
+            case 839:
+            case 840:
+            case 893:
+            case 1169:
+            case 1215:
+            case 1216:
+            case 1217:
+            case 1364:
+            case 1451:
+            case 1557:
+            case 22001: // H2
+            case 22003:
+            case 22012:
+            case 22018:
+            case 22025:
+            case 23000:
+            case 23002:
+            case 23502:
+            case 23506:
+            case 23507:
+            case 23513:
+                context.related("Constraint Violation")
+                        .whatToDo("Report this, there is an SQL Constraint Violation.");
+                break;
+            default:
+                context.related("Unknown SQL Error code");
+        }
+        return new DBOpException("SQL Failure: " + e.getMessage(), e, context.build());
+    }
+
+    // Checkstyle.ON: CyclomaticComplexity
+
+    @Override
+    public Optional<ErrorContext> getContext() {
+        return Optional.ofNullable(context);
+    }
 }
\ No newline at end of file
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/extension/ExtensionSvc.java b/Plan/common/src/main/java/com/djrapitops/plan/extension/ExtensionSvc.java
index e6aefa3e8..564e5f9c5 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/extension/ExtensionSvc.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/extension/ExtensionSvc.java
@@ -23,12 +23,14 @@ import com.djrapitops.plan.exceptions.DataExtensionMethodCallException;
 import com.djrapitops.plan.extension.implementation.CallerImplementation;
 import com.djrapitops.plan.extension.implementation.ExtensionRegister;
 import com.djrapitops.plan.extension.implementation.ExtensionWrapper;
+import com.djrapitops.plan.extension.implementation.providers.MethodWrapper;
 import com.djrapitops.plan.extension.implementation.providers.gathering.ProviderValueGatherer;
 import com.djrapitops.plan.identification.ServerInfo;
 import com.djrapitops.plan.processing.Processing;
 import com.djrapitops.plan.settings.config.ExtensionSettings;
 import com.djrapitops.plan.settings.config.PlanConfig;
 import com.djrapitops.plan.storage.database.DBSystem;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -88,8 +90,14 @@ public class ExtensionSvc implements ExtensionService {
         try {
             extensionRegister.registerBuiltInExtensions(config.getExtensionSettings().getDisabled());
         } catch (IllegalStateException failedToRegisterOne) {
-            logger.warn("One or more extensions failed to register, see suppressed exceptions (They can be disabled in Plan config).");
-            errorLogger.log(L.WARN, ExtensionService.class, failedToRegisterOne);
+            ErrorContext.Builder context = ErrorContext.builder()
+                    .whatToDo("Report and/or disable the failed extensions. You can find the failed extensions in the error file.");
+            for (Throwable suppressedException : failedToRegisterOne.getSuppressed()) {
+                context.related(suppressedException.getMessage());
+            }
+
+            logger.warn("One or more extensions failed to register (They can be disabled in Plan config).");
+            errorLogger.log(L.WARN, failedToRegisterOne, context.build());
         }
     }
 
@@ -130,7 +138,9 @@ public class ExtensionSvc implements ExtensionService {
             try {
                 pluginsConfig.createSection(pluginName);
             } catch (IOException e) {
-                errorLogger.log(L.ERROR, this.getClass(), e);
+                errorLogger.log(L.WARN, e, ErrorContext.builder()
+                        .whatToDo("Create 'Plugins." + pluginName + ".Enabled: true' setting manually.")
+                        .related("Section: " + pluginName).build());
                 logger.warn("Could not register DataExtension for " + pluginName + " due to " + e.toString());
                 return true;
             }
@@ -165,21 +175,23 @@ public class ExtensionSvc implements ExtensionService {
             // Try again
             updatePlayerValues(gatherer, playerUUID, playerName, event);
         } catch (Exception | NoClassDefFoundError | NoSuchFieldError | NoSuchMethodError unexpectedError) {
-            logger.warn("Encountered unexpected error with " + gatherer.getPluginName() + " Extension: " + unexpectedError +
-                    " (but failed safely) when updating value for '" + playerName +
-                    "', stack trace to follow (please report this):");
-            errorLogger.log(L.WARN, gatherer.getClass(), unexpectedError);
+            ErrorContext.Builder context = ErrorContext.builder()
+                    .whatToDo("Report and/or disable " + gatherer.getPluginName() + " extension in the Plan config.")
+                    .related(gatherer.getPluginName())
+                    .related(event)
+                    .related("Player: " + playerName + " " + playerUUID);
+            errorLogger.log(L.WARN, unexpectedError, context.build());
         }
     }
 
     private void logFailure(String playerName, DataExtensionMethodCallException methodCallFailed) {
         Throwable cause = methodCallFailed.getCause();
-        String causeName = cause.getClass().getSimpleName();
-        logger.warn("Encountered " + causeName + " with " + methodCallFailed.getPluginName() + " Extension" +
-                " (failed safely) when updating value for '" + playerName +
-                "', the method was disabled temporarily (won't be called until next Plan reload)" +
-                ", stack trace to follow (please report this):");
-        errorLogger.log(L.WARN, getClass(), cause);
+        ErrorContext.Builder context = ErrorContext.builder()
+                .whatToDo("Report and/or disable " + methodCallFailed.getPluginName() + " extension in the Plan config.")
+                .related(methodCallFailed.getPluginName())
+                .related("Method:" + methodCallFailed.getMethod().map(MethodWrapper::getMethodName).orElse("-"))
+                .related("Player: " + playerName);
+        errorLogger.log(L.WARN, cause, context.build());
     }
 
     public void updateServerValues(CallEvents event) {
@@ -206,9 +218,12 @@ public class ExtensionSvc implements ExtensionService {
             // Try again
             updateServerValues(gatherer, event);
         } catch (Exception | NoClassDefFoundError | NoSuchFieldError | NoSuchMethodError unexpectedError) {
-            logger.warn("Encountered unexpected error with " + gatherer.getPluginName() + " Extension: " + unexpectedError +
-                    " (failed safely) when updating value for server, stack trace to follow (please report this):");
-            errorLogger.log(L.WARN, gatherer.getClass(), unexpectedError);
+            ErrorContext.Builder context = ErrorContext.builder()
+                    .whatToDo("Report and/or disable " + gatherer.getPluginName() + " extension in the Plan config.")
+                    .related(gatherer.getPluginName())
+                    .related(event)
+                    .related("Gathering for server");
+            errorLogger.log(L.WARN, unexpectedError, context.build());
         }
     }
 }
\ No newline at end of file
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/gathering/ServerShutdownSave.java b/Plan/common/src/main/java/com/djrapitops/plan/gathering/ServerShutdownSave.java
index f50ec17a3..e7a0ac3f9 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/gathering/ServerShutdownSave.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/gathering/ServerShutdownSave.java
@@ -25,6 +25,7 @@ import com.djrapitops.plan.settings.locale.lang.PluginLang;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.Database;
 import com.djrapitops.plan.storage.database.transactions.events.ServerShutdownTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -90,7 +91,11 @@ public abstract class ServerShutdownSave {
             prepareSessionsForStorage(activeSessions, System.currentTimeMillis());
             return Optional.of(saveActiveSessions(activeSessions));
         } catch (DBInitException e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder()
+                    .whatToDo("Find the sessions in the error file and save them manually or ignore. Report & delete the error file after.")
+                    .related("Shutdown save failed to init database.")
+                    .related(activeSessions)
+                    .build());
             return Optional.empty();
         } catch (IllegalStateException ignored) {
             /* Database is not initialized */
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/gathering/cache/NicknameCache.java b/Plan/common/src/main/java/com/djrapitops/plan/gathering/cache/NicknameCache.java
index f12fd23a4..343d5efca 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/gathering/cache/NicknameCache.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/gathering/cache/NicknameCache.java
@@ -99,7 +99,7 @@ public class NicknameCache implements SubSystem {
                     NicknameQueries.fetchLastSeenNicknameOfPlayer(uuid, serverInfo.getServerUUID())
             ).map(Nickname::getName);
         } catch (DBOpException e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e);
         }
         return Optional.empty();
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/gathering/timed/SystemUsageBuffer.java b/Plan/common/src/main/java/com/djrapitops/plan/gathering/timed/SystemUsageBuffer.java
index 2a6affd3a..848860519 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/gathering/timed/SystemUsageBuffer.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/gathering/timed/SystemUsageBuffer.java
@@ -19,6 +19,7 @@ package com.djrapitops.plan.gathering.timed;
 import com.djrapitops.plan.gathering.SystemUsage;
 import com.djrapitops.plan.settings.config.PlanConfig;
 import com.djrapitops.plan.settings.config.paths.DataGatheringSettings;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -111,7 +112,8 @@ public class SystemUsageBuffer {
                 buffer.freeDiskSpace = SystemUsage.getFreeDiskSpace();
             } catch (SecurityException noPermission) {
                 if (!diskErrored) {
-                    errorLogger.log(L.WARN, this.getClass(), noPermission);
+                    errorLogger.log(L.WARN, noPermission, ErrorContext.builder()
+                            .whatToDo("Resolve " + noPermission.getMessage() + " via OS or JVM permissions").build());
                 }
                 diskErrored = true;
             } catch (Exception e) {
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/gathering/timed/TPSCounter.java b/Plan/common/src/main/java/com/djrapitops/plan/gathering/timed/TPSCounter.java
index c4c4cd652..fa70c093f 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/gathering/timed/TPSCounter.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/gathering/timed/TPSCounter.java
@@ -16,6 +16,7 @@
  */
 package com.djrapitops.plan.gathering.timed;
 
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -45,7 +46,7 @@ public abstract class TPSCounter extends AbsRunnable {
             pulse();
         } catch (Exception | NoClassDefFoundError | NoSuchMethodError | NoSuchFieldError e) {
             logger.error("TPS Count Task Disabled due to error, reload Plan to re-enable.");
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().whatToDo("See if a restart fixes this or Report this").build());
             cancel();
         }
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/identification/ServerServerInfo.java b/Plan/common/src/main/java/com/djrapitops/plan/identification/ServerServerInfo.java
index dd33a24b0..6db74f0ed 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/identification/ServerServerInfo.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/identification/ServerServerInfo.java
@@ -27,6 +27,7 @@ import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.Database;
 import com.djrapitops.plan.storage.database.queries.objects.ServerQueries;
 import com.djrapitops.plan.storage.database.transactions.StoreServerInformationTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 
@@ -113,8 +114,11 @@ public class ServerServerInfo extends ServerInfo {
         if (!foundServer.isPresent()) {
             try {
                 server = registerServer(serverUUID);
-            } catch (ExecutionException | IOException e) {
-                errorLogger.log(L.CRITICAL, this.getClass(), e);
+            } catch (IOException e) {
+                errorLogger.log(L.CRITICAL, e, ErrorContext.builder()
+                        .whatToDo("Grant access permissions for writing to " + serverInfoFile.getConfigFilePath()).build());
+            } catch (ExecutionException e) {
+                errorLogger.log(L.CRITICAL, e, ErrorContext.builder().build());
             } catch (InterruptedException e) {
                 Thread.currentThread().interrupt();
             }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/identification/UUIDUtility.java b/Plan/common/src/main/java/com/djrapitops/plan/identification/UUIDUtility.java
index 650deabff..3cab1154a 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/identification/UUIDUtility.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/identification/UUIDUtility.java
@@ -92,7 +92,7 @@ public class UUIDUtility {
         try {
             return dbSystem.getDatabase().query(UserIdentifierQueries.fetchPlayerUUIDOf(playerName));
         } catch (DBOpException e) {
-            errorLogger.log(L.ERROR, UUIDUtility.class, e);
+            errorLogger.log(L.ERROR, e);
             return Optional.empty();
         }
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/processing/Processing.java b/Plan/common/src/main/java/com/djrapitops/plan/processing/Processing.java
index 3f84dc7ff..181fde9b5 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/processing/Processing.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/processing/Processing.java
@@ -19,6 +19,7 @@ package com.djrapitops.plan.processing;
 import com.djrapitops.plan.SubSystem;
 import com.djrapitops.plan.settings.locale.Locale;
 import com.djrapitops.plan.settings.locale.lang.PluginLang;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -58,7 +59,7 @@ public class Processing implements SubSystem {
                 new BasicThreadFactory.Builder()
                         .namingPattern(s)
                         .uncaughtExceptionHandler((thread, throwable) ->
-                                errorLogger.log(L.WARN, Processing.class, throwable)
+                                errorLogger.log(L.WARN, throwable, ErrorContext.builder().build())
                         ).build());
     }
 
@@ -110,14 +111,14 @@ public class Processing implements SubSystem {
 
     private <T> T exceptionHandlerNonCritical(T t, Throwable throwable) {
         if (throwable != null) {
-            errorLogger.log(L.WARN, Processing.class, throwable.getCause());
+            errorLogger.log(L.WARN, throwable.getCause(), ErrorContext.builder().build());
         }
         return t;
     }
 
     private <T> T exceptionHandlerCritical(T t, Throwable throwable) {
         if (throwable != null) {
-            errorLogger.log(L.ERROR, Processing.class, throwable.getCause());
+            errorLogger.log(L.ERROR, throwable.getCause(), ErrorContext.builder().build());
         }
         return t;
     }
@@ -163,7 +164,7 @@ public class Processing implements SubSystem {
             try {
                 runnable.run();
             } catch (Exception | NoClassDefFoundError | NoSuchMethodError | NoSuchFieldError e) {
-                errorLogger.log(L.WARN, this.getClass(), e);
+                errorLogger.log(L.WARN, e, ErrorContext.builder().build());
             }
         }
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/query/QuerySvc.java b/Plan/common/src/main/java/com/djrapitops/plan/query/QuerySvc.java
index a42299551..0482728d9 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/query/QuerySvc.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/query/QuerySvc.java
@@ -23,6 +23,7 @@ import com.djrapitops.plan.storage.database.Database;
 import com.djrapitops.plan.storage.database.queries.QueryAPIExecutable;
 import com.djrapitops.plan.storage.database.queries.QueryAPIQuery;
 import com.djrapitops.plan.storage.database.transactions.Transaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -107,8 +108,9 @@ public class QuerySvc implements QueryService {
             try {
                 subscriber.accept(playerUUID);
             } catch (DBOpException e) {
-                logger.warn("User of Query API (" + subscriber.getClass().getName() + ") ran into exception, failed safely:");
-                errorLogger.log(L.WARN, QueryService.class, e);
+                errorLogger.log(L.WARN, e, ErrorContext.builder()
+                        .whatToDo("Report to this Query API user " + subscriber.getClass().getName())
+                        .related("Subscriber: " + subscriber.getClass().getName()).build());
             }
         });
     }
@@ -118,8 +120,9 @@ public class QuerySvc implements QueryService {
             try {
                 function.apply();
             } catch (DBOpException e) {
-                logger.warn("User of Query API (" + function.getClass().getName() + ") ran into exception, failed safely:");
-                errorLogger.log(L.WARN, QueryService.class, e);
+                errorLogger.log(L.WARN, e, ErrorContext.builder()
+                        .whatToDo("Report to this Query API user " + function.getClass().getName())
+                        .related("Subscriber: " + function.getClass().getName()).build());
             }
         });
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/settings/ConfigSystem.java b/Plan/common/src/main/java/com/djrapitops/plan/settings/ConfigSystem.java
index 55905f2ae..12429a693 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/settings/ConfigSystem.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/settings/ConfigSystem.java
@@ -24,6 +24,7 @@ import com.djrapitops.plan.settings.config.paths.FormatSettings;
 import com.djrapitops.plan.settings.config.paths.PluginSettings;
 import com.djrapitops.plan.settings.theme.Theme;
 import com.djrapitops.plan.storage.file.PlanFiles;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -86,7 +87,7 @@ public abstract class ConfigSystem implements SubSystem {
 
             checkWrongTimeZone();
         } catch (IOException e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().whatToDo("Fix write permissions to " + config.getConfigFilePath()).build());
             throw new EnableException("Failed to save default config: " + e.getMessage(), e);
         }
         theme.enable();
@@ -134,7 +135,7 @@ public abstract class ConfigSystem implements SubSystem {
         try {
             config.read();
         } catch (IOException e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().whatToDo("Fix read permissions to " + config.getConfigFilePath()).build());
         }
     }
 }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/settings/SettingsSvc.java b/Plan/common/src/main/java/com/djrapitops/plan/settings/SettingsSvc.java
index 668ea23fe..ef2434804 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/settings/SettingsSvc.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/settings/SettingsSvc.java
@@ -18,6 +18,7 @@ package com.djrapitops.plan.settings;
 
 import com.djrapitops.plan.settings.config.ConfigNode;
 import com.djrapitops.plan.settings.config.PlanConfig;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 
@@ -70,7 +71,7 @@ public class SettingsSvc implements SettingsService {
         try {
             config.save();
         } catch (IOException e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().whatToDo("Fix write permissions to " + config.getConfigFilePath()).build());
         }
     }
 
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/settings/config/Config.java b/Plan/common/src/main/java/com/djrapitops/plan/settings/config/Config.java
index 5cbc930e2..309bf5a9d 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/settings/config/Config.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/settings/config/Config.java
@@ -98,4 +98,8 @@ public class Config extends ConfigNode {
     public int hashCode() {
         return Objects.hash(super.hashCode(), configFilePath);
     }
+
+    public Path getConfigFilePath() {
+        return configFilePath;
+    }
 }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/settings/config/WorldAliasSettings.java b/Plan/common/src/main/java/com/djrapitops/plan/settings/config/WorldAliasSettings.java
index 9fab3fc57..6923ca304 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/settings/config/WorldAliasSettings.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/settings/config/WorldAliasSettings.java
@@ -27,6 +27,7 @@ import com.djrapitops.plan.settings.config.paths.DisplaySettings;
 import com.djrapitops.plan.settings.locale.Locale;
 import com.djrapitops.plan.settings.locale.lang.GenericLang;
 import com.djrapitops.plan.settings.locale.lang.HtmlLang;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.utilities.Verify;
@@ -93,7 +94,7 @@ public class WorldAliasSettings {
                 try {
                     aliasSect.save();
                 } catch (IOException e) {
-                    errorLogger.log(L.WARN, WorldAliasSettings.class, e);
+                    errorLogger.log(L.ERROR, e, ErrorContext.builder().whatToDo("Fix write permissions to " + config.get().getConfigFilePath()).build());
                 }
             });
         }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/settings/config/changes/ConfigUpdater.java b/Plan/common/src/main/java/com/djrapitops/plan/settings/config/changes/ConfigUpdater.java
index d47d84d4a..f1341b59a 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/settings/config/changes/ConfigUpdater.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/settings/config/changes/ConfigUpdater.java
@@ -18,6 +18,7 @@ package com.djrapitops.plan.settings.config.changes;
 
 import com.djrapitops.plan.settings.config.Config;
 import com.djrapitops.plan.settings.config.paths.FormatSettings;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -152,7 +153,9 @@ public class ConfigUpdater {
                     logger.info("Config: " + change.getAppliedMessage());
                 }
             } catch (Exception e) {
-                errorLogger.log(L.WARN, this.getClass(), new IllegalStateException("Failed to apply config update: '" + change.getAppliedMessage() + "'", e));
+                errorLogger.log(L.ERROR, e, ErrorContext.builder()
+                        .whatToDo("Fix write permissions to " + config.getConfigFilePath() + " or Report this")
+                        .related("Attempt to change: " + change.getAppliedMessage()).build());
             }
         }
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/settings/locale/LocaleSystem.java b/Plan/common/src/main/java/com/djrapitops/plan/settings/locale/LocaleSystem.java
index 24590d6cc..a835d2a78 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/settings/locale/LocaleSystem.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/settings/locale/LocaleSystem.java
@@ -22,6 +22,7 @@ import com.djrapitops.plan.settings.config.PlanConfig;
 import com.djrapitops.plan.settings.config.paths.PluginSettings;
 import com.djrapitops.plan.settings.locale.lang.*;
 import com.djrapitops.plan.storage.file.PlanFiles;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -112,8 +113,7 @@ public class LocaleSystem implements SubSystem {
             }
             new LocaleFileWriter(writing).writeToFile(localeFile);
         } catch (IOException | IllegalStateException e) {
-            logger.error("Failed to write new Locale file at " + localeFile.getAbsolutePath());
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().whatToDo("Fix write permissions to " + localeFile.getAbsolutePath()).build());
         }
         resetWriteConfigSetting();
     }
@@ -123,8 +123,7 @@ public class LocaleSystem implements SubSystem {
             config.set(PluginSettings.WRITE_NEW_LOCALE, false);
             config.save();
         } catch (IOException | IllegalStateException e) {
-            logger.error("Failed set WriteNewLocaleFileOnEnable back to false");
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().whatToDo("Fix write permissions to " + config.getConfigFilePath()).build());
         }
     }
 
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/settings/upkeep/FileWatcher.java b/Plan/common/src/main/java/com/djrapitops/plan/settings/upkeep/FileWatcher.java
index d12feb43f..ed0874dbe 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/settings/upkeep/FileWatcher.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/settings/upkeep/FileWatcher.java
@@ -16,6 +16,7 @@
  */
 package com.djrapitops.plan.settings.upkeep;
 
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.utilities.Verify;
@@ -75,7 +76,7 @@ public class FileWatcher extends Thread {
             watchedPath.register(watcher, ENTRY_MODIFY);
             runLoop(watcher);
         } catch (IOException e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().build());
             interrupt();
         } catch (InterruptedException e) {
             interrupt();
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/storage/database/MySQLDB.java b/Plan/common/src/main/java/com/djrapitops/plan/storage/database/MySQLDB.java
index 90541fabd..c5a963258 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/storage/database/MySQLDB.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/storage/database/MySQLDB.java
@@ -23,6 +23,7 @@ import com.djrapitops.plan.settings.config.PlanConfig;
 import com.djrapitops.plan.settings.config.paths.DatabaseSettings;
 import com.djrapitops.plan.settings.locale.Locale;
 import com.djrapitops.plan.settings.locale.lang.PluginLang;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -76,7 +77,7 @@ public class MySQLDB extends SQLDB {
         try {
             Class.forName("com.mysql.cj.jdbc.Driver");
         } catch (ClassNotFoundException e) {
-            errorLogger.log(L.CRITICAL, this.getClass(), e);
+            errorLogger.log(L.CRITICAL, e, ErrorContext.builder().whatToDo("Install MySQL Driver to the server").build());
         }
     }
 
@@ -164,7 +165,7 @@ public class MySQLDB extends SQLDB {
                 connection.close();
             }
         } catch (SQLException e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.CRITICAL, e, ErrorContext.builder().related("Closing connection").build());
         }
     }
 
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/storage/database/SQLDB.java b/Plan/common/src/main/java/com/djrapitops/plan/storage/database/SQLDB.java
index ba69ebeb5..1f2ad3f2c 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/storage/database/SQLDB.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/storage/database/SQLDB.java
@@ -31,6 +31,7 @@ import com.djrapitops.plan.storage.database.transactions.init.CreateTablesTransa
 import com.djrapitops.plan.storage.database.transactions.init.OperationCriticalTransaction;
 import com.djrapitops.plan.storage.database.transactions.patches.*;
 import com.djrapitops.plan.utilities.java.ThrowableUtils;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.api.TimeAmount;
 import com.djrapitops.plugin.logging.L;
@@ -92,7 +93,9 @@ public abstract class SQLDB extends AbstractDatabase {
                     .namingPattern(nameFormat)
                     .uncaughtExceptionHandler((thread, throwable) -> {
                         if (devMode) {
-                            errorLogger.log(L.WARN, getClass(), throwable);
+                            errorLogger.log(L.WARN, throwable, ErrorContext.builder()
+                                    .whatToDo("THIS ERROR IS ONLY LOGGED IN DEV MODE")
+                                    .build());
                         }
                     }).build());
         };
@@ -248,10 +251,10 @@ public abstract class SQLDB extends AbstractDatabase {
             }
             transaction.executeTransaction(this);
             return CompletableFuture.completedFuture(null);
-        }, getTransactionExecutor()).handle(errorHandler(origin));
+        }, getTransactionExecutor()).handle(errorHandler(transaction, origin));
     }
 
-    private BiFunction<CompletableFuture<Object>, Throwable, CompletableFuture<Object>> errorHandler(Exception origin) {
+    private BiFunction<CompletableFuture<Object>, Throwable, CompletableFuture<Object>> errorHandler(Transaction transaction, Exception origin) {
         return (obj, throwable) -> {
             if (throwable == null) {
                 return CompletableFuture.completedFuture(null);
@@ -261,7 +264,8 @@ public abstract class SQLDB extends AbstractDatabase {
             }
             ThrowableUtils.appendEntryPointToCause(throwable, origin);
 
-            errorLogger.log(L.ERROR, getClass(), throwable);
+            errorLogger.log(L.ERROR, throwable, ErrorContext.builder()
+                    .related("Transaction: " + transaction.getClass()).build());
             return CompletableFuture.completedFuture(null);
         };
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/storage/database/SQLiteDB.java b/Plan/common/src/main/java/com/djrapitops/plan/storage/database/SQLiteDB.java
index d8307817a..b17c8a78b 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/storage/database/SQLiteDB.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/storage/database/SQLiteDB.java
@@ -25,6 +25,7 @@ import com.djrapitops.plan.storage.file.PlanFiles;
 import com.djrapitops.plan.storage.upkeep.DBKeepAliveTask;
 import com.djrapitops.plan.utilities.MiscUtils;
 import com.djrapitops.plan.utilities.java.ThrowableUtils;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -80,8 +81,8 @@ public class SQLiteDB extends SQLDB {
         try {
             Class.forName("org.sqlite.JDBC");
         } catch (ClassNotFoundException e) {
-            errorLogger.log(L.CRITICAL, this.getClass(), e);
-            return null; // Should never happen.
+            errorLogger.log(L.CRITICAL, e, ErrorContext.builder().whatToDo("Install SQLite Driver to the server").build());
+            return null;
         }
 
         String dbFilePath = dbFile.getAbsolutePath();
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/DBCleanTask.java b/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/DBCleanTask.java
index 09c1b6070..f7f3fc6ec 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/DBCleanTask.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/DBCleanTask.java
@@ -115,7 +115,7 @@ public class DBCleanTask extends AbsRunnable {
                 }
             }
         } catch (DBOpException e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e);
             cancel();
         }
     }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/DBKeepAliveTask.java b/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/DBKeepAliveTask.java
index 13ddb4bb0..5cfc59ba6 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/DBKeepAliveTask.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/storage/upkeep/DBKeepAliveTask.java
@@ -17,6 +17,7 @@
 package com.djrapitops.plan.storage.upkeep;
 
 import com.djrapitops.plan.utilities.MiscUtils;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.djrapitops.plugin.logging.console.PluginLogger;
@@ -59,7 +60,8 @@ public class DBKeepAliveTask extends AbsRunnable {
             try {
                 connection = iReconnect.reconnect();
             } catch (SQLException reconnectionError) {
-                errorLogger.log(L.ERROR, this.getClass(), reconnectionError);
+                errorLogger.log(L.ERROR, reconnectionError, ErrorContext.builder()
+                        .whatToDo("Reload Plan and Report this if the issue persists").build());
                 logger.error("SQL connection maintaining task had to be closed due to exception.");
                 this.cancel();
             }
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/utilities/logging/ErrorContext.java b/Plan/common/src/main/java/com/djrapitops/plan/utilities/logging/ErrorContext.java
index ee65e2e42..3652179fa 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/utilities/logging/ErrorContext.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/utilities/logging/ErrorContext.java
@@ -42,12 +42,17 @@ public class ErrorContext {
 
     public Collection<String> toLines() {
         List<String> lines = new ArrayList<>();
+        getWhatToDo().ifPresent(lines::add);
         for (Object o : related) {
             lines.add(Objects.toString(o));
         }
         return lines;
     }
 
+    public void merge(ErrorContext context) {
+        this.related.addAll(context.related);
+    }
+
     public static class Builder {
         private final ErrorContext context;
 
diff --git a/Plan/common/src/main/java/com/djrapitops/plan/utilities/logging/ErrorLogger.java b/Plan/common/src/main/java/com/djrapitops/plan/utilities/logging/ErrorLogger.java
index 4e3c94675..aebcd8088 100644
--- a/Plan/common/src/main/java/com/djrapitops/plan/utilities/logging/ErrorLogger.java
+++ b/Plan/common/src/main/java/com/djrapitops/plan/utilities/logging/ErrorLogger.java
@@ -18,6 +18,7 @@ package com.djrapitops.plan.utilities.logging;
 
 import com.djrapitops.plan.PlanPlugin;
 import com.djrapitops.plan.delivery.formatting.Formatters;
+import com.djrapitops.plan.exceptions.ExceptionWithContext;
 import com.djrapitops.plan.identification.properties.ServerProperties;
 import com.djrapitops.plan.storage.file.PlanFiles;
 import com.djrapitops.plan.utilities.java.Lists;
@@ -76,11 +77,16 @@ public class ErrorLogger implements ErrorHandler {
         this.formatters = formatters;
     }
 
+    public <T extends ExceptionWithContext> void log(L level, T throwable) {
+        log(level, (Throwable) throwable, throwable.getContext().orElse(ErrorContext.builder().related("Missing Context").build()));
+    }
+
     public void log(L level, Throwable throwable, ErrorContext context) {
         String errorName = throwable.getClass().getSimpleName();
         String hash = hash(throwable);
         Path logsDir = files.getLogsDirectory();
         Path errorLog = logsDir.resolve(errorName + "-" + hash + ".txt");
+        mergeAdditionalContext(throwable, context);
         if (Files.exists(errorLog)) {
             logExisting(errorLog, throwable, context);
         } else {
@@ -93,6 +99,16 @@ public class ErrorLogger implements ErrorHandler {
         }
     }
 
+    public void mergeAdditionalContext(Throwable throwable, ErrorContext context) {
+        Throwable cause = throwable.getCause();
+        while (cause != null) {
+            if (cause instanceof ExceptionWithContext) {
+                ((ExceptionWithContext) cause).getContext().ifPresent(context::merge);
+            }
+            cause = cause.getCause();
+        }
+    }
+
     private void logExisting(Path errorLog, Throwable throwable, ErrorContext context) {
         // Read existing
         List<String> lines;
@@ -232,6 +248,13 @@ public class ErrorLogger implements ErrorHandler {
         for (StackTraceElement element : e.getStackTrace()) {
             trace.add("   " + element);
         }
+        Throwable[] suppressed = e.getSuppressed();
+        if (suppressed.length > 0) {
+            for (Throwable suppressedThrowable : suppressed) {
+                trace.add("   Suppressed:");
+                buildReadableStacktrace(suppressedThrowable).stream().map(line -> "   " + line).forEach(trace::add);
+            }
+        }
         Throwable cause = e.getCause();
         if (cause != null) {
             trace.add("Caused by:");
diff --git a/Plan/nukkit/src/main/java/com/djrapitops/plan/addons/placeholderapi/NukkitPlaceholderRegistrar.java b/Plan/nukkit/src/main/java/com/djrapitops/plan/addons/placeholderapi/NukkitPlaceholderRegistrar.java
index 47ec480b2..d9863fbb8 100644
--- a/Plan/nukkit/src/main/java/com/djrapitops/plan/addons/placeholderapi/NukkitPlaceholderRegistrar.java
+++ b/Plan/nukkit/src/main/java/com/djrapitops/plan/addons/placeholderapi/NukkitPlaceholderRegistrar.java
@@ -24,12 +24,12 @@ import com.djrapitops.plan.delivery.domain.keys.PlayerKeys;
 import com.djrapitops.plan.gathering.cache.SessionCache;
 import com.djrapitops.plan.placeholder.PlanPlaceholders;
 import com.djrapitops.plan.storage.database.queries.containers.ContainerFetchQueries;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 
 import javax.inject.Inject;
 import javax.inject.Singleton;
-import java.util.ArrayList;
 import java.util.UUID;
 
 /**
@@ -60,9 +60,9 @@ public class NukkitPlaceholderRegistrar {
         placeholders.getPlaceholders().forEach((name, loader) ->
                 api.visitorSensitivePlaceholder(name, (player, params) -> {
                             try {
-                                return loader.apply(getPlayer(player), new ArrayList<>(params.getAll().values()));
+                                return loader.apply(getPlayer(player), params.get());
                             } catch (Exception e) {
-                                errorLogger.log(L.WARN, getClass(), e);
+                                errorLogger.log(L.WARN, e, ErrorContext.builder().related("Registering PlaceholderAPI").build());
                                 return null;
                             }
                         }
@@ -71,9 +71,9 @@ public class NukkitPlaceholderRegistrar {
         placeholders.getStaticPlaceholders().forEach((name, loader) ->
                 api.staticPlaceholder(name, params -> {
                             try {
-                                return loader.apply(new ArrayList<>(params.getAll().values()));
+                                return loader.apply(params.get());
                             } catch (Exception e) {
-                                errorLogger.log(L.WARN, getClass(), e);
+                                errorLogger.log(L.WARN, e, ErrorContext.builder().related("Registering PlaceholderAPI").build());
                                 return null;
                             }
                         }
diff --git a/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/ChatListener.java b/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/ChatListener.java
index 5b8800bbe..381f9c97d 100644
--- a/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/ChatListener.java
+++ b/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/ChatListener.java
@@ -26,6 +26,7 @@ import com.djrapitops.plan.gathering.cache.NicknameCache;
 import com.djrapitops.plan.identification.ServerInfo;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.transactions.events.NicknameStoreTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 
@@ -66,7 +67,7 @@ public class ChatListener implements Listener {
         try {
             actOnChatEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
diff --git a/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/DeathEventListener.java b/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/DeathEventListener.java
index facaa5d6f..73d57f10a 100644
--- a/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/DeathEventListener.java
+++ b/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/DeathEventListener.java
@@ -35,6 +35,7 @@ import com.djrapitops.plan.gathering.domain.Session;
 import com.djrapitops.plan.processing.Processing;
 import com.djrapitops.plan.processing.processors.player.MobKillProcessor;
 import com.djrapitops.plan.processing.processors.player.PlayerKillProcessor;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 
@@ -78,7 +79,7 @@ public class DeathEventListener implements Listener {
             UUID uuid = dead.getUniqueId();
             handleKill(time, uuid, killerEntity);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event, dead).build());
         }
     }
 
@@ -98,7 +99,7 @@ public class DeathEventListener implements Listener {
 
             handleKill(time, /* Not a player */ null, killerEntity);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event, dead).build());
         }
     }
 
diff --git a/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/GameModeChangeListener.java b/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/GameModeChangeListener.java
index b21301bc6..5a267b02b 100644
--- a/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/GameModeChangeListener.java
+++ b/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/GameModeChangeListener.java
@@ -28,6 +28,7 @@ import com.djrapitops.plan.identification.ServerInfo;
 import com.djrapitops.plan.settings.config.WorldAliasSettings;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.transactions.events.WorldNameStoreTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 
@@ -68,7 +69,7 @@ public class GameModeChangeListener implements Listener {
         try {
             actOnEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event, event.getPlayer().getGamemode() + "->" + event.getNewGamemode()).build());
         }
     }
 
diff --git a/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/NukkitAFKListener.java b/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/NukkitAFKListener.java
index d19c281a4..021850395 100644
--- a/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/NukkitAFKListener.java
+++ b/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/NukkitAFKListener.java
@@ -24,6 +24,7 @@ import cn.nukkit.event.player.*;
 import com.djrapitops.plan.gathering.afk.AFKTracker;
 import com.djrapitops.plan.settings.Permissions;
 import com.djrapitops.plan.settings.config.PlanConfig;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 
@@ -79,7 +80,7 @@ public class NukkitAFKListener implements Listener {
 
             AFK_TRACKER.performedAction(uuid, time);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
diff --git a/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/PlayerOnlineListener.java b/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/PlayerOnlineListener.java
index 3383d2d19..3edc5d33f 100644
--- a/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/PlayerOnlineListener.java
+++ b/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/PlayerOnlineListener.java
@@ -45,6 +45,7 @@ import com.djrapitops.plan.settings.config.paths.ExportSettings;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.Database;
 import com.djrapitops.plan.storage.database.transactions.events.*;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 
@@ -105,7 +106,7 @@ public class PlayerOnlineListener implements Listener {
             boolean operator = event.getPlayer().isOp();
             dbSystem.getDatabase().executeTransaction(new OperatorStatusTransaction(playerUUID, operator));
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
@@ -130,7 +131,7 @@ public class PlayerOnlineListener implements Listener {
 
             dbSystem.getDatabase().executeTransaction(new KickStoreTransaction(uuid));
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
@@ -139,7 +140,7 @@ public class PlayerOnlineListener implements Listener {
         try {
             actOnJoinEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
@@ -204,7 +205,7 @@ public class PlayerOnlineListener implements Listener {
         try {
             actOnQuitEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
diff --git a/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/WorldChangeListener.java b/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/WorldChangeListener.java
index 9db0b87b1..30ee392a6 100644
--- a/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/WorldChangeListener.java
+++ b/Plan/nukkit/src/main/java/com/djrapitops/plan/gathering/listeners/nukkit/WorldChangeListener.java
@@ -28,6 +28,7 @@ import com.djrapitops.plan.identification.ServerInfo;
 import com.djrapitops.plan.settings.config.WorldAliasSettings;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.transactions.events.WorldNameStoreTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 
@@ -61,7 +62,7 @@ public class WorldChangeListener implements Listener {
             try {
                 actOnEvent(event);
             } catch (Exception e) {
-                errorLogger.log(L.ERROR, this.getClass(), e);
+                errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
             }
         }
     }
diff --git a/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/PlayerOnlineListener.java b/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/PlayerOnlineListener.java
index dc4ed0f26..0f7117340 100644
--- a/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/PlayerOnlineListener.java
+++ b/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/PlayerOnlineListener.java
@@ -36,6 +36,7 @@ import com.djrapitops.plan.settings.config.paths.ExportSettings;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.Database;
 import com.djrapitops.plan.storage.database.transactions.events.*;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import org.spongepowered.api.Sponge;
@@ -105,7 +106,7 @@ public class PlayerOnlineListener {
         try {
             actOnLoginEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
@@ -125,7 +126,7 @@ public class PlayerOnlineListener {
             }
             dbSystem.getDatabase().executeTransaction(new KickStoreTransaction(playerUUID));
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
@@ -143,7 +144,7 @@ public class PlayerOnlineListener {
         try {
             actOnJoinEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
@@ -208,7 +209,7 @@ public class PlayerOnlineListener {
         try {
             actOnQuitEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
diff --git a/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeAFKListener.java b/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeAFKListener.java
index c9a6930cc..2bf9e87dd 100644
--- a/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeAFKListener.java
+++ b/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeAFKListener.java
@@ -19,6 +19,7 @@ package com.djrapitops.plan.gathering.listeners.sponge;
 import com.djrapitops.plan.gathering.afk.AFKTracker;
 import com.djrapitops.plan.settings.Permissions;
 import com.djrapitops.plan.settings.config.PlanConfig;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import org.spongepowered.api.entity.living.player.Player;
@@ -71,7 +72,7 @@ public class SpongeAFKListener {
         try {
             performedAction(event.getTargetEntity());
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
diff --git a/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeChatListener.java b/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeChatListener.java
index 111f48f0b..1898ac78a 100644
--- a/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeChatListener.java
+++ b/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeChatListener.java
@@ -21,6 +21,7 @@ import com.djrapitops.plan.gathering.cache.NicknameCache;
 import com.djrapitops.plan.identification.ServerInfo;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.transactions.events.NicknameStoreTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import org.spongepowered.api.entity.living.player.Player;
@@ -66,7 +67,7 @@ public class SpongeChatListener {
         try {
             actOnChatEvent(player);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
diff --git a/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeDeathListener.java b/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeDeathListener.java
index 87495df0d..b5c49d96d 100644
--- a/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeDeathListener.java
+++ b/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeDeathListener.java
@@ -23,6 +23,7 @@ import com.djrapitops.plan.gathering.domain.Session;
 import com.djrapitops.plan.processing.Processing;
 import com.djrapitops.plan.processing.processors.player.MobKillProcessor;
 import com.djrapitops.plan.processing.processors.player.PlayerKillProcessor;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import org.spongepowered.api.data.key.Keys;
@@ -81,7 +82,7 @@ public class SpongeDeathListener {
                 handleKill(time, dead, killerEntity);
             }
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event, dead).build());
         }
     }
 
diff --git a/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeGMChangeListener.java b/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeGMChangeListener.java
index 1226afe99..f3348aa7e 100644
--- a/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeGMChangeListener.java
+++ b/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeGMChangeListener.java
@@ -22,6 +22,7 @@ import com.djrapitops.plan.identification.ServerInfo;
 import com.djrapitops.plan.settings.config.WorldAliasSettings;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.transactions.events.WorldNameStoreTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import org.spongepowered.api.entity.living.player.Player;
@@ -67,7 +68,7 @@ public class SpongeGMChangeListener {
         try {
             actOnGMChangeEvent(event);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event, event.getGameMode()).build());
         }
     }
 
diff --git a/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeWorldChangeListener.java b/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeWorldChangeListener.java
index 2673b0443..c25ab1d4d 100644
--- a/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeWorldChangeListener.java
+++ b/Plan/sponge/src/main/java/com/djrapitops/plan/gathering/listeners/sponge/SpongeWorldChangeListener.java
@@ -22,6 +22,7 @@ import com.djrapitops.plan.identification.ServerInfo;
 import com.djrapitops.plan.settings.config.WorldAliasSettings;
 import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.transactions.events.WorldNameStoreTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import org.spongepowered.api.data.key.Keys;
@@ -70,7 +71,7 @@ public class SpongeWorldChangeListener {
         try {
             actOnEvent(event, player);
         } catch (Exception e) {
-            errorLogger.log(L.ERROR, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
diff --git a/Plan/velocity/src/main/java/com/djrapitops/plan/gathering/listeners/velocity/PlayerOnlineListener.java b/Plan/velocity/src/main/java/com/djrapitops/plan/gathering/listeners/velocity/PlayerOnlineListener.java
index c98fcb1ec..f4cc648e0 100644
--- a/Plan/velocity/src/main/java/com/djrapitops/plan/gathering/listeners/velocity/PlayerOnlineListener.java
+++ b/Plan/velocity/src/main/java/com/djrapitops/plan/gathering/listeners/velocity/PlayerOnlineListener.java
@@ -34,6 +34,7 @@ import com.djrapitops.plan.storage.database.DBSystem;
 import com.djrapitops.plan.storage.database.Database;
 import com.djrapitops.plan.storage.database.transactions.events.GeoInfoStoreTransaction;
 import com.djrapitops.plan.storage.database.transactions.events.PlayerRegisterTransaction;
+import com.djrapitops.plan.utilities.logging.ErrorContext;
 import com.djrapitops.plan.utilities.logging.ErrorLogger;
 import com.djrapitops.plugin.logging.L;
 import com.velocitypowered.api.event.PostOrder;
@@ -96,7 +97,7 @@ public class PlayerOnlineListener {
         try {
             actOnLogin(event);
         } catch (Exception e) {
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
@@ -147,7 +148,7 @@ public class PlayerOnlineListener {
         try {
             actOnLogout(event);
         } catch (Exception e) {
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }
 
@@ -185,7 +186,7 @@ public class PlayerOnlineListener {
         try {
             actOnServerSwitch(event);
         } catch (Exception e) {
-            errorLogger.log(L.WARN, this.getClass(), e);
+            errorLogger.log(L.ERROR, e, ErrorContext.builder().related(event).build());
         }
     }