diff --git a/ChaosBot/Attribute/AssemblyController.cs b/ChaosBot/Attribute/AssemblyController.cs
new file mode 100644
index 0000000..b7fb2de
--- /dev/null
+++ b/ChaosBot/Attribute/AssemblyController.cs
@@ -0,0 +1,73 @@
+using System;
+using System.Collections.Generic;
+using System.Linq;
+using System.Reflection;
+using ChaosBot.Database;
+using Microsoft.Data.Sqlite;
+using NLog;
+
+namespace ChaosBot.Attribute
+{
+    public static class AssemblyController
+    {
+        private static Logger _logger = Program._logger;
+        public static void Register()
+        {
+            Assembly dbEntityAssembly = Assembly.GetAssembly(typeof(DBEntity));
+            if (dbEntityAssembly != null)
+            {
+                foreach (Type type in dbEntityAssembly.GetTypes())
+                {
+                    if (type.GetCustomAttributes(typeof(DBEntity), true).Length > 0)
+                    {
+                        // type == all classes that have [DBEntity(...)]
+                        
+                        // Get a reference to the attribute
+                        DBEntity dbEntity = type.GetCustomAttributes(typeof(DBEntity)).Cast<DBEntity>().First();
+
+                        string table = dbEntity.Table;
+                        // TODO: Generate this in one go instead of many separate commands
+                        Controller.RawQuery($"CREATE TABLE IF NOT EXISTS {table} (id INTEGER NOT NULL CONSTRAINT {table}_pk PRIMARY KEY AUTOINCREMENT)");
+                        
+                        foreach (MethodInfo field in type.GetMethods())
+                        {
+                            if (field.Name.StartsWith("get_"))
+                            {
+                                try
+                                {
+                                    // TODO: Use an attribute to detect primary autoincrement key
+                                    if (field.Name == "id")
+                                    {
+                                        Controller.RawQuery($"CREATE UNIQUE INDEX {table}_id_uindex ON {table} (id)", false, true);
+                                        continue;
+                                    }
+                                    
+                                    string fieldname = field.Name.Substring(4);
+                                    string fieldType = DBEntity.DataTypes.GetValueOrDefault(field.ReturnType).ToString();
+                                    string fieldModifiers = null;
+
+                                    string query = $"ALTER TABLE {table} ADD COLUMN {fieldname} {fieldType} {fieldModifiers}";
+                                    Controller.RawQuery(query, false, true);
+                                }
+                                catch (Exception ex)
+                                {
+                                    if (ex is SqliteException sqliteException)
+                                    {
+                                        if (!sqliteException.Message.Contains("duplicate column name"))
+                                        {
+                                            _logger.Fatal($"AssemblyController.Register: Exception [{ex}] thrown, <[{ex.Message}]>.");
+                                        }
+                                    }
+                                    else
+                                    {
+                                        _logger.Error($"AssemblyController.Register: Exception [{ex}] thrown, <[{ex.Message}]>.");
+                                    }
+                                }
+                            }
+                        }
+                    }
+                }
+            }
+        }
+    }
+}
\ No newline at end of file
diff --git a/ChaosBot/Attribute/DBEntity.cs b/ChaosBot/Attribute/DBEntity.cs
new file mode 100644
index 0000000..4cf1804
--- /dev/null
+++ b/ChaosBot/Attribute/DBEntity.cs
@@ -0,0 +1,40 @@
+using System;
+using System.Collections.Generic;
+using Microsoft.Data.Sqlite;
+
+namespace ChaosBot.Attribute
+{
+    [AttributeUsage(AttributeTargets.Class)]
+    public class DBEntity : System.Attribute
+    {
+        public readonly string Table;
+
+        public static readonly Dictionary<Type, SqliteType> DataTypes = new Dictionary<Type, SqliteType>
+        {
+            {typeof(bool), SqliteType.Integer},
+            {typeof(byte), SqliteType.Integer},
+            {typeof(byte[]), SqliteType.Blob},
+            {typeof(char), SqliteType.Text},
+            {typeof(DateTime), SqliteType.Text},
+            {typeof(DateTimeOffset), SqliteType.Text},
+            {typeof(Decimal), SqliteType.Text},
+            {typeof(Double), SqliteType.Real},
+            {typeof(Guid), SqliteType.Text},
+            {typeof(Int16), SqliteType.Integer},
+            {typeof(Int32), SqliteType.Integer},
+            {typeof(Int64), SqliteType.Integer},
+            {typeof(SByte), SqliteType.Integer},
+            {typeof(Single), SqliteType.Real},
+            {typeof(String), SqliteType.Text},
+            {typeof(TimeSpan), SqliteType.Text},
+            {typeof(UInt16), SqliteType.Integer},
+            {typeof(UInt32), SqliteType.Integer},
+            {typeof(UInt64), SqliteType.Integer}
+        }; 
+        
+        public DBEntity(string table)
+        {
+            this.Table = table;
+        }
+    }
+}
\ No newline at end of file
diff --git a/ChaosBot/Database/Controller.cs b/ChaosBot/Database/Controller.cs
index f7599fc..103672a 100644
--- a/ChaosBot/Database/Controller.cs
+++ b/ChaosBot/Database/Controller.cs
@@ -15,7 +15,7 @@ namespace ChaosBot.Database
         static SqliteConnection _conn = new SqliteConnection($"Data Source={System.IO.Directory.GetCurrentDirectory()}/{Program.Cfg.GetValue<string>("Bot:Database")}");
         private static Logger _logger = Program._logger;
         
-        public static DataTable RawQuery(string query)
+        public static DataTable RawQuery(string query, bool readOutput = true, bool throwError = false)
         {
             DataTable dt = new DataTable();
             
@@ -27,15 +27,27 @@ namespace ChaosBot.Database
 
                     SqliteCommand cmd = _conn.CreateCommand();
                     cmd.CommandText = query;
-                    SqliteDataReader executeReader = cmd.ExecuteReader(CommandBehavior.SingleResult);
-                    
-                    dt.Load(executeReader);
-                    
+
+                    if (readOutput)
+                    {
+                        SqliteDataReader executeReader = cmd.ExecuteReader(CommandBehavior.SingleResult);
+                        dt.Load(executeReader);
+                    }
+                    else
+                    {
+                        cmd.ExecuteNonQuery();
+                    }
+
                     _conn.Close();
                 }
             }
             catch (Exception ex)
             {
+                if (throwError)
+                {
+                    throw;
+                }
+
                 _logger.Fatal($"Controllers.DBWork.RawQuery: Exception [{ex}] thrown, <[{ex.Message}]>.");
             }
             
diff --git a/ChaosBot/Database/Entity/Raffle.cs b/ChaosBot/Database/Entity/Raffle.cs
index 9abba6c..de8f954 100644
--- a/ChaosBot/Database/Entity/Raffle.cs
+++ b/ChaosBot/Database/Entity/Raffle.cs
@@ -1,5 +1,8 @@
+using ChaosBot.Attribute;
+
 namespace ChaosBot.Database.Entity
 {
+    [DBEntity("RaffleTable")]
     public class Raffle
     {
         public int id { get; }
diff --git a/ChaosBot/Program.cs b/ChaosBot/Program.cs
index ed60476..e882adb 100644
--- a/ChaosBot/Program.cs
+++ b/ChaosBot/Program.cs
@@ -1,7 +1,9 @@
 using NLog;
 using System;
+using System.Reflection;
 using ChaosBot.Discord;
 using System.Threading.Tasks;
+using ChaosBot.Attribute;
 using Microsoft.Extensions.Configuration;
 
 
@@ -34,6 +36,12 @@ namespace ChaosBot
                  * Initialize the _logger for logging purposes
                  */
                 _logger = Logging.GenLog();
+                
+                
+                /*
+                 * Attempt to load our custom assemblies
+                 */
+                AssemblyController.Register();
 
                 /*
                  * Initialize the Discord Client and Login