diff --git a/MultiUserRaffleBot/Models/ConfigData.cs b/MultiUserRaffleBot/Models/ConfigData.cs
index 458829c..bb3f768 100644
--- a/MultiUserRaffleBot/Models/ConfigData.cs
+++ b/MultiUserRaffleBot/Models/ConfigData.cs
@@ -87,6 +87,9 @@ public class ConfigData
         [JsonProperty]
         public int MaxMessageLifetime = 5;
 
+        [JsonProperty]
+        public bool EnableLogging = false;
+
         /*** Config Loading/Saving ***/
         public static ConfigData? LoadConfigData()
         {
diff --git a/MultiUserRaffleBot/Models/ConsoleService.cs b/MultiUserRaffleBot/Models/ConsoleService.cs
index 1d543b0..8e2cb9e 100644
--- a/MultiUserRaffleBot/Models/ConsoleService.cs
+++ b/MultiUserRaffleBot/Models/ConsoleService.cs
@@ -7,6 +7,7 @@
 using MultiUserRaffleBot.Types;
 using Avalonia.Controls;
 using System.Linq;
+using System.IO;
 
 namespace MultiUserRaffleBot.Models
 {
@@ -34,17 +35,22 @@ public class ConsoleService : BaseServiceTickable
         public ObservableCollection<ConsoleMessage> ConsoleMessages { get; private set; }
         public static DataGrid? ConsoleHistory;
         private int MaxMessageLifetime = 5;
+        private static string LogFileName = "log.txt";
+        private bool LoggingEnabled = false;
 
         public ConsoleService()
         {
             ConsoleMessages = [];
+            if (File.Exists(LogFileName))
+                File.Delete(LogFileName);
         }
 
         public override ConsoleSources GetSource() => ConsoleSources.None;
 
-        public void SetMaxMessageLifetime(int value)
+        public void ApplySettings(int messageLifetime, bool enableLogs)
         {
-            MaxMessageLifetime = value;
+            MaxMessageLifetime = messageLifetime;
+            LoggingEnabled = enableLogs;
         }
 
         public void AddMessage(string inMessage, ConsoleSources source = ConsoleSources.None)
@@ -53,6 +59,8 @@ public void AddMessage(string inMessage, ConsoleSources source = ConsoleSources.
             if (string.IsNullOrWhiteSpace(inMessage))
                 return;
 
+            PrintToLog(inMessage, source);
+
             Dispatcher.UIThread.Post(() => {
                 ConsoleMessages.Add(new ConsoleMessage(inMessage, source));
                 ConsoleHistory?.ScrollIntoView(ConsoleMessages.Last(), null);
@@ -69,6 +77,18 @@ public void ClearAllMessages()
             Dispatcher.UIThread.Post(() => ConsoleMessages.Clear());
         }
 
+        private void PrintToLog(string inMessage, ConsoleSources source)
+        {
+            if (!LoggingEnabled)
+                return;
+
+            // Print out the winner to a log file.
+            using (StreamWriter FileWriter = File.AppendText(LogFileName))
+            {
+                FileWriter.WriteLine($"[{DateTime.Now}]({source}) {inMessage}");
+            }
+        }
+
         protected override async Task Tick()
         {
             using PeriodicTimer timer = new(TimeSpan.FromSeconds(30));
diff --git a/MultiUserRaffleBot/Models/TwitchService.cs b/MultiUserRaffleBot/Models/TwitchService.cs
index f8a53f0..3c38979 100644
--- a/MultiUserRaffleBot/Models/TwitchService.cs
+++ b/MultiUserRaffleBot/Models/TwitchService.cs
@@ -26,16 +26,18 @@ public class TwitchService : BaseService
     {
         private readonly TwitchClient client;
         private readonly TwitchSettings settings;
-        private Random rng = new();
+        private Random rng = new Random(Guid.NewGuid().GetHashCode());
         private CancellationTokenSource cancelToken = new();
 
         // Raffle Data
-        private const string WinnerLogFile = "raffle.txt";
         private bool RaffleOpen = false;
+        private const string WinnerLogFile = "raffle.txt";
+        private Collection<string> Entries = new();
+
+        // Raffle Strings
         private string CurrentRaffleMessage = string.Empty;
         private string CurrentRafflePrize = string.Empty;
         private string CurrentWinnerName = string.Empty;
-        private Collection<string> Entries = new();
 
         public override ConsoleSources GetSource() => ConsoleSources.Twitch;
 
@@ -135,28 +137,6 @@ public void JoinChannels(TwitchSettings NewSettings)
         }
 
         /*** Raffle Support ***/
-        private void SetCurrentRaffleMessage(RaffleState state, int raffleLength = 600)
-        {
-            switch (state)
-            {
-                case RaffleState.RaffleOpen:
-                    CurrentRaffleMessage = $"Drawing is now open for {CurrentRafflePrize} for {raffleLength / 60} minutes! Type !enter to enter.";
-                    break;
-                case RaffleState.WinnerPicked:
-                    CurrentRaffleMessage = $"Winner of {CurrentRafflePrize} is @{CurrentWinnerName}! Type !confirm within 5 minutes to confirm!";
-                    break;
-                case RaffleState.Claimed:
-                    CurrentRaffleMessage = $"{CurrentRafflePrize} claimed by @{CurrentWinnerName}! Congrats! {settings.WinnerInstructions}";
-                    break;
-                case RaffleState.NoEntries:
-                    CurrentRaffleMessage = $"Drawing for prize {CurrentRafflePrize} ended with no claims. Prize may appear again in the future...";
-                    break;
-                default:
-                    CurrentRaffleMessage = "";
-                    break;
-            }
-        }
-
         public void StartRaffle(string rafflePrize, int raffleLength)
         {
             // If the raffle prize string is just empty, skip the command
@@ -164,7 +144,6 @@ public void StartRaffle(string rafflePrize, int raffleLength)
                 return;
 
             RaffleOpen = true;
-            Entries.Clear();
             CurrentRafflePrize = rafflePrize;
             SetCurrentRaffleMessage(RaffleState.RaffleOpen, raffleLength);
 
@@ -201,7 +180,7 @@ public void PickRaffle()
             }
 
             // Choose a winner
-            int ChooseIndex = rng.Next(Entries.Count);
+            int ChooseIndex = rng.Next(0, Entries.Count);
             CurrentWinnerName = Entries[ChooseIndex].ToLower();
 
             // Print a message
@@ -230,7 +209,29 @@ private void WriteRaffleResult(string winner)
             {
                 FileWriter.WriteLine($"{CurrentRafflePrize} winner is {winner}");
             }
-            CurrentRafflePrize = string.Empty;
+            ResetRaffle();
+        }
+
+        private void SetCurrentRaffleMessage(RaffleState state, int raffleLength = 600)
+        {
+            switch (state)
+            {
+                case RaffleState.RaffleOpen:
+                    CurrentRaffleMessage = $"Drawing is now open for {CurrentRafflePrize} for {raffleLength / 60} minutes! Type !enter to enter.";
+                    break;
+                case RaffleState.WinnerPicked:
+                    CurrentRaffleMessage = $"Winner of {CurrentRafflePrize} is @{CurrentWinnerName}! Type !confirm within 5 minutes to confirm!";
+                    break;
+                case RaffleState.Claimed:
+                    CurrentRaffleMessage = $"{CurrentRafflePrize} claimed by @{CurrentWinnerName}! Congrats! {settings.WinnerInstructions}";
+                    break;
+                case RaffleState.NoEntries:
+                    CurrentRaffleMessage = $"Drawing for prize {CurrentRafflePrize} ended with no claims. Prize may appear again in the future...";
+                    break;
+                default:
+                    CurrentRaffleMessage = string.Empty;
+                    break;
+            }
         }
 
         private void CancelWait()
@@ -240,6 +241,13 @@ private void CancelWait()
             cancelToken = new();
         }
 
+        private void ResetRaffle()
+        {
+            CurrentRafflePrize = string.Empty;
+            CurrentWinnerName = string.Empty;
+            Entries.Clear();
+        }
+
         /*** Handle Twitch Events ***/
         private void OnChannelJoined(object unused, OnJoinedChannelArgs args)
         {
@@ -264,6 +272,7 @@ private void OnCommandReceived(object unused, OnChatCommandReceivedArgs args)
                 if (RaffleOpen && !Entries.Contains(user))
                 {
                     Entries.Add(user);
+                    PrintMessage($"{user} entered at index {Entries.Count}");
                     if (settings.RespondToRaffleEntry)
                         SendMessageToChannel(args.Command.ChatMessage.Channel, $"@{user} you have entered!");
                 }
@@ -275,6 +284,7 @@ private void OnCommandReceived(object unused, OnChatCommandReceivedArgs args)
                     CancelWait();
 
                     // Push updates to everyone
+                    PrintMessage($"{CurrentWinnerName} has claimed the prize {CurrentRafflePrize}");
                     SetCurrentRaffleMessage(RaffleState.Claimed);
                     WriteRaffleResult(CurrentWinnerName);
                     SendCurrentStatusToAllChannels();
diff --git a/MultiUserRaffleBot/ViewModels/MainViewModel.cs b/MultiUserRaffleBot/ViewModels/MainViewModel.cs
index ba9f06a..28f0e01 100644
--- a/MultiUserRaffleBot/ViewModels/MainViewModel.cs
+++ b/MultiUserRaffleBot/ViewModels/MainViewModel.cs
@@ -102,7 +102,7 @@ private void LoadConfigs()
         }
 
         // Set the max message lifetime
-        Console.SetMaxMessageLifetime(Config.MaxMessageLifetime);
+        Console.ApplySettings(Config.MaxMessageLifetime, Config.EnableLogging);
         Raffle.BuildRaffleData(Config.RaffleData);
     }