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 4c483d499..05755dd3b 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
@@ -148,7 +148,7 @@ public abstract class SQLDB extends AbstractDatabase {
 
     @Override
     public void init() {
-        List<Runnable> unfinishedTransactions = closeTransactionExecutor(transactionExecutor);
+        List<Runnable> unfinishedTransactions = forceCloseTransactionExecutor();
         this.transactionExecutor = transactionExecutorServiceProvider.get();
 
         setState(State.PATCHING);
@@ -167,9 +167,9 @@ public abstract class SQLDB extends AbstractDatabase {
         }
     }
 
-    private List<Runnable> closeTransactionExecutor(ExecutorService transactionExecutor) {
+    protected boolean attemptToCloseTransactionExecutor() {
         if (transactionExecutor == null || transactionExecutor.isShutdown() || transactionExecutor.isTerminated()) {
-            return Collections.emptyList();
+            return true;
         }
         transactionExecutor.shutdown();
         try {
@@ -179,20 +179,27 @@ public abstract class SQLDB extends AbstractDatabase {
                 logger.warn(TimeSettings.DB_TRANSACTION_FINISH_WAIT_DELAY.getPath() + " was set to over 5 minutes, using 5 min instead.");
                 waitMs = TimeUnit.MINUTES.toMillis(5L);
             }
-            if (!transactionExecutor.awaitTermination(waitMs, TimeUnit.MILLISECONDS)) {
-                List<Runnable> unfinished = transactionExecutor.shutdownNow();
-                int unfinishedCount = unfinished.size();
-                if (unfinishedCount > 0) {
-                    logger.warn(unfinishedCount + " unfinished database transactions were not executed.");
-                }
-                return unfinished;
-            }
+            return transactionExecutor.awaitTermination(waitMs, TimeUnit.MILLISECONDS);
         } catch (InterruptedException e) {
             Thread.currentThread().interrupt();
+        }
+        return true;
+    }
+
+    protected List<Runnable> forceCloseTransactionExecutor() {
+        if (transactionExecutor == null || transactionExecutor.isShutdown() || transactionExecutor.isTerminated()) {
+            return Collections.emptyList();
+        }
+        try {
+            List<Runnable> unfinished = transactionExecutor.shutdownNow();
+            int unfinishedCount = unfinished.size();
+            if (unfinishedCount > 0) {
+                logger.warn(unfinishedCount + " unfinished database transactions were not executed.");
+            }
+            return unfinished;
         } finally {
             logger.info(locale.getString(PluginLang.DISABLED_WAITING_TRANSACTIONS_COMPLETE));
         }
-        return Collections.emptyList();
     }
 
     Patch[] patches() {
@@ -307,13 +314,18 @@ public abstract class SQLDB extends AbstractDatabase {
 
     @Override
     public void close() {
+        // SQLiteDB Overrides this, so any additions to this should also be reflected there.
         if (getState() == State.OPEN) setState(State.CLOSING);
-        closeTransactionExecutor(transactionExecutor);
+        if (attemptToCloseTransactionExecutor()) {
+            logger.info(locale.getString(PluginLang.DISABLED_WAITING_TRANSACTIONS_COMPLETE));
+        } else {
+            forceCloseTransactionExecutor();
+        }
         unloadDriverClassloader();
         setState(State.CLOSED);
     }
 
-    private void unloadDriverClassloader() {
+    protected void unloadDriverClassloader() {
         // Unloading class loader using close() causes issues when reloading.
         // It is better to leak this memory than crash the plugin on reload.
 
@@ -349,6 +361,8 @@ public abstract class SQLDB extends AbstractDatabase {
 
         return CompletableFuture.supplyAsync(() -> {
             try {
+                if (getState() == State.CLOSED) return CompletableFuture.completedFuture(null);
+
                 accessLock.performDatabaseOperation(() -> {
                     if (!ranIntoFatalError.get()) {transaction.executeTransaction(this);}
                 }, transaction);
@@ -360,6 +374,9 @@ public abstract class SQLDB extends AbstractDatabase {
     }
 
     private boolean determineIfShouldDropUnimportantTransactions(int queueSize) {
+        if (getState() == State.CLOSING) {
+            return true;
+        }
         boolean dropTransactions = dropUnimportantTransactions.get();
         if (queueSize >= 500 && !dropTransactions) {
             logger.warn("Database queue size: " + queueSize + ", dropping some unimportant transactions. If this keeps happening disable some extensions or optimize MySQL.");
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 3d105ec3d..ff2149183 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
@@ -201,11 +201,21 @@ public class SQLiteDB extends SQLDB {
 
     @Override
     public void close() {
-        super.close();
+        if (getState() == State.OPEN) setState(State.CLOSING);
+        boolean transactionQueueClosed = attemptToCloseTransactionExecutor();
+        if (transactionQueueClosed) logger.info(locale.getString(PluginLang.DISABLED_WAITING_TRANSACTIONS_COMPLETE));
+
+        unloadDriverClassloader();
+        setState(State.CLOSED);
+
         stopConnectionPingTask();
 
         logger.info(locale.getString(PluginLang.DISABLED_WAITING_SQLITE));
         connectionLock.waitUntilNothingAccessing();
+
+        // Transaction queue can't be force-closed before all connections have terminated.
+        if (!transactionQueueClosed) forceCloseTransactionExecutor();
+
         if (connection != null) {
             MiscUtils.close(connection);
         }