diff --git a/LLama/ChatSession.cs b/LLama/ChatSession.cs
index d1504a08..2985bd5f 100644
--- a/LLama/ChatSession.cs
+++ b/LLama/ChatSession.cs
@@ -1,243 +1,496 @@
-using LLama.Abstractions;
-using LLama.Common;
 using System;
 using System.Collections.Generic;
 using System.IO;
 using System.Linq;
 using System.Runtime.CompilerServices;
-using System.Text;
 using System.Threading;
 using System.Threading.Tasks;
+using LLama.Abstractions;
+using LLama.Common;
 using static LLama.InteractiveExecutor;
 
-namespace LLama
+namespace LLama;
+
+/// <summary>
+/// The main chat session class.
+/// </summary>
+public class ChatSession
 {
+    private const string _modelStateFilename = "ModelState.st";
+    private const string _executorStateFilename = "ExecutorState.json";
+    private const string _hsitoryFilename = "ChatHistory.json";
+
     /// <summary>
-    /// The main chat session class.
-    /// </summary>
-    public class ChatSession
-    {
-        private readonly ILLamaExecutor _executor;
-        private readonly ChatHistory _history;
-
-        private const string _executorStateFilename = "ExecutorState.json";
-        private const string _modelStateFilename = "ModelState.st";
-
-        /// <summary>
-        /// The executor for this session.
-        /// </summary>
-        public ILLamaExecutor Executor => _executor;
-        /// <summary>
-        /// The chat history for this session.
-        /// </summary>
-        public ChatHistory History => _history;
-        /// <summary>
-        /// The history transform used in this session.
-        /// </summary>
-        public IHistoryTransform HistoryTransform { get; set; } = new LLamaTransforms.DefaultHistoryTransform();
-        /// <summary>
-        /// The input transform pipeline used in this session.
-        /// </summary>
-        public List<ITextTransform> InputTransformPipeline { get; set; } = new();
-        /// <summary>
-        /// The output transform used in this session.
-        /// </summary>
-        public ITextStreamTransform OutputTransform = new LLamaTransforms.EmptyTextOutputStreamTransform();
-
-        /// <summary>
-        /// 
-        /// </summary>
-        /// <param name="executor">The executor for this session</param>
-        public ChatSession(ILLamaExecutor executor)
-        {
-            _executor = executor;
-            _history = new ChatHistory();
-        }
-
-        /// <summary>
-        /// Use a custom history transform.
-        /// </summary>
-        /// <param name="transform"></param>
-        /// <returns></returns>
-        public ChatSession WithHistoryTransform(IHistoryTransform transform)
-        {
-            HistoryTransform = transform;
-            return this;
-        }
-
-        /// <summary>
-        /// Add a text transform to the input transform pipeline.
-        /// </summary>
-        /// <param name="transform"></param>
-        /// <returns></returns>
-        public ChatSession AddInputTransform(ITextTransform transform)
-        {
-            InputTransformPipeline.Add(transform);
-            return this;
-        }
-
-        /// <summary>
-        /// Use a custom output transform.
-        /// </summary>
-        /// <param name="transform"></param>
-        /// <returns></returns>
-        public ChatSession WithOutputTransform(ITextStreamTransform transform)
-        {
-            OutputTransform = transform;
-            return this;
-        }
-
-        /// <summary>
-        /// 
-        /// </summary>
-        /// <param name="path">The directory name to save the session. If the directory does not exist, a new directory will be created.</param>
-        public virtual void SaveSession(string path)
-        {
-            if (!Directory.Exists(path))
-            {
-                Directory.CreateDirectory(path);
-            }
-            _executor.Context.SaveState(Path.Combine(path, _modelStateFilename));
-            if (Executor is StatelessExecutor)
-            {
+    /// The executor for this session.
+    /// </summary>
+    public ILLamaExecutor Executor { get; private set; }
 
-            }
-            else if (Executor is StatefulExecutorBase statefulExecutor)
-            {
-                statefulExecutor.SaveState(Path.Combine(path, _executorStateFilename));
-            }
-            else
-            {
-                throw new System.NotImplementedException("You're using a customized executor. Please inherit ChatSession and rewrite the method.");
-            }
+    /// <summary>
+    /// The chat history for this session.
+    /// </summary>
+    public ChatHistory History { get; private set; } = new();
+
+    /// <summary>
+    /// The history transform used in this session.
+    /// </summary>
+    public IHistoryTransform HistoryTransform { get; set; } = new LLamaTransforms.DefaultHistoryTransform();
+
+    /// <summary>
+    /// The input transform pipeline used in this session.
+    /// </summary>
+    public List<ITextTransform> InputTransformPipeline { get; set; } = new();
+
+    /// <summary>
+    /// The output transform used in this session.
+    /// </summary>
+    public ITextStreamTransform OutputTransform = new LLamaTransforms.EmptyTextOutputStreamTransform();
+
+    /// <summary>
+    /// Create a new chat session.
+    /// </summary>
+    /// <param name="executor">The executor for this session</param>
+    public ChatSession(ILLamaExecutor executor)
+    {
+        // Check if executor has StatefulExecutorBase as base class
+        if (executor is not StatefulExecutorBase)
+        {
+            throw new ArgumentException("Executor must have a StatefulExecutorBase", nameof(executor));
         }
 
-        /// <summary>
-        /// 
-        /// </summary>
-        /// <param name="path">The directory name to load the session.</param>
-        public virtual void LoadSession(string path)
+        Executor = executor;
+    }
+
+    /// <summary>
+    /// Create a new chat session with a custom history.
+    /// </summary>
+    /// <param name="executor"></param>
+    /// <param name="history"></param>
+    public ChatSession(ILLamaExecutor executor, ChatHistory history)
+        : this(executor)
+    {
+        History = history;
+    }
+
+    /// <summary>
+    /// Use a custom history transform.
+    /// </summary>
+    /// <param name="transform"></param>
+    /// <returns></returns>
+    public ChatSession WithHistoryTransform(IHistoryTransform transform)
+    {
+        HistoryTransform = transform;
+        return this;
+    }
+
+    /// <summary>
+    /// Add a text transform to the input transform pipeline.
+    /// </summary>
+    /// <param name="transform"></param>
+    /// <returns></returns>
+    public ChatSession AddInputTransform(ITextTransform transform)
+    {
+        InputTransformPipeline.Add(transform);
+        return this;
+    }
+
+    /// <summary>
+    /// Use a custom output transform.
+    /// </summary>
+    /// <param name="transform"></param>
+    /// <returns></returns>
+    public ChatSession WithOutputTransform(ITextStreamTransform transform)
+    {
+        OutputTransform = transform;
+        return this;
+    }
+
+    /// <summary>
+    /// Save a session from a directory.
+    /// </summary>
+    /// <param name="path"></param>
+    /// <returns></returns>
+    /// <exception cref="ArgumentException"></exception>
+    public void SaveSession(string path)
+    {
+        if (string.IsNullOrWhiteSpace(path))
         {
-            if (!Directory.Exists(path))
-            {
-                throw new FileNotFoundException($"Directory {path} does not exist.");
-            }
-            _executor.Context.LoadState(Path.Combine(path, _modelStateFilename));
-            if (Executor is StatelessExecutor)
-            {
+            throw new ArgumentException("Path cannot be null or whitespace", nameof(path));
+        }
 
-            }
-            else if (Executor is StatefulExecutorBase statefulExecutor)
+        if (Directory.Exists(path))
+        {
+            Directory.Delete(path, recursive: true);
+        }
+
+        Directory.CreateDirectory(path);
+
+        string modelStateFilePath = Path.Combine(path, _modelStateFilename);
+        Executor.Context.SaveState(modelStateFilePath);
+
+        string executorStateFilepath = Path.Combine(path, _executorStateFilename);
+        ((StatefulExecutorBase)Executor).SaveState(executorStateFilepath);
+
+        string historyFilepath = Path.Combine(path, _hsitoryFilename);
+        File.WriteAllText(historyFilepath, History.ToJson());
+    }
+
+    /// <summary>
+    /// Load a session from a directory.
+    /// </summary>
+    /// <param name="path"></param>
+    /// <returns></returns>
+    /// <exception cref="ArgumentException"></exception>
+    public void LoadSession(string path)
+    {
+        if (string.IsNullOrWhiteSpace(path))
+        {
+            throw new ArgumentException("Path cannot be null or whitespace", nameof(path));
+        }
+
+        if (!Directory.Exists(path))
+        {
+            throw new ArgumentException("Directory does not exist", nameof(path));
+        }
+
+        string modelStateFilePath = Path.Combine(path, _modelStateFilename);
+        Executor.Context.LoadState(modelStateFilePath);
+
+        string executorStateFilepath = Path.Combine(path, _executorStateFilename);
+        ((StatefulExecutorBase)Executor).LoadState(executorStateFilepath);
+
+        string historyFilepath = Path.Combine(path, _hsitoryFilename);
+        string historyJson = File.ReadAllText(historyFilepath);
+        History = ChatHistory.FromJson(historyJson)
+            ?? throw new ArgumentException("History file is invalid", nameof(path));
+    }
+
+    /// <summary>
+    /// Add a message to the chat history.
+    /// </summary>
+    /// <param name="message"></param>
+    /// <returns></returns>
+    public ChatSession AddMessage(ChatHistory.Message message)
+    {
+        // If current message is a system message, only allow the history to be empty
+        if (message.AuthorRole == AuthorRole.System && History.Messages.Count > 0)
+        {
+            throw new ArgumentException("Cannot add a system message after another message", nameof(message));
+        }
+
+        // If current message is a user message, only allow the history to be empty,
+        // or the previous message to be a system message or assistant message.
+        if (message.AuthorRole == AuthorRole.User)
+        {
+            ChatHistory.Message? lastMessage = History.Messages.LastOrDefault();
+            if (lastMessage is not null && lastMessage.AuthorRole == AuthorRole.User)
             {
-                statefulExecutor.LoadState(Path.Combine(path, _executorStateFilename));
+                throw new ArgumentException("Cannot add a user message after another user message", nameof(message));
             }
-            else
+        }
+
+        // If the current message is an assistant message,
+        // the previous message must be a user message.
+        if (message.AuthorRole == AuthorRole.Assistant)
+        {
+            ChatHistory.Message? lastMessage = History.Messages.LastOrDefault();
+            if (lastMessage is null
+                || lastMessage.AuthorRole != AuthorRole.User)
             {
-                throw new System.NotImplementedException("You're using a customized executor. Please inherit ChatSession and rewrite the method.");
+                throw new ArgumentException("Assistant message must be preceeded with a user message", nameof(message));
             }
         }
 
-        /// <summary>
-        /// Generates a response for a given user prompt and manages history state for the user.
-        /// This will always pass the whole history to the model. Don't pass a whole history
-        /// to this method as the user prompt will be appended to the history of the current session.
-        /// If more control is needed, use the other overload of this method that accepts a ChatHistory object.
-        /// </summary>
-        /// <param name="prompt"></param>
-        /// <param name="inferenceParams"></param>
-        /// <param name="cancellationToken"></param>
-        /// <returns>Returns generated text of the assistant message.</returns>
-        public async IAsyncEnumerable<string> ChatAsync(string prompt, IInferenceParams? inferenceParams = null, [EnumeratorCancellation] CancellationToken cancellationToken = default)
+        History.AddMessage(message.AuthorRole, message.Content);
+        return this;
+    }
+
+    /// <summary>
+    /// Add a system message to the chat history.
+    /// </summary>
+    /// <param name="content"></param>
+    /// <returns></returns>
+    public ChatSession AddSystemMessage(string content)
+        => AddMessage(new ChatHistory.Message(AuthorRole.System, content));
+
+    /// <summary>
+    /// Add an assistant message to the chat history.
+    /// </summary>
+    /// <param name="content"></param>
+    /// <returns></returns>
+    public ChatSession AddAssistantMessage(string content)
+        => AddMessage(new ChatHistory.Message(AuthorRole.Assistant, content));
+
+    /// <summary>
+    /// Add a user message to the chat history.
+    /// </summary>
+    /// <param name="content"></param>
+    /// <returns></returns>
+    public ChatSession AddUserMessage(string content)
+        => AddMessage(new ChatHistory.Message(AuthorRole.User, content));
+
+    /// <summary>
+    /// Remove the last message from the chat history.
+    /// </summary>
+    /// <returns></returns>
+    public ChatSession RemoveLastMessage()
+    {
+        History.Messages.RemoveAt(History.Messages.Count - 1);
+        return this;
+    }
+
+    /// <summary>
+    /// Replace a user message with a new message and remove all messages after the new message.
+    /// This is useful when the user wants to edit a message. And regenerate the response.
+    /// </summary>
+    /// <param name="oldMessage"></param>
+    /// <param name="newMessage"></param>
+    /// <returns></returns>
+    public ChatSession ReplaceUserMessage(
+        ChatHistory.Message oldMessage,
+        ChatHistory.Message newMessage)
+    {
+        if (oldMessage.AuthorRole != AuthorRole.User)
+        {
+            throw new ArgumentException("Old message must be a user message", nameof(oldMessage));
+        }
+
+        if (newMessage.AuthorRole != AuthorRole.User)
         {
-            foreach (var inputTransform in InputTransformPipeline)
-                prompt = inputTransform.Transform(prompt);
+            throw new ArgumentException("New message must be a user message", nameof(newMessage));
+        }
 
-            History.Messages.Add(new ChatHistory.Message(AuthorRole.User, prompt));
+        int index = History.Messages.IndexOf(oldMessage);
+        if (index == -1)
+        {
+            throw new ArgumentException("Old message does not exist in history", nameof(oldMessage));
+        }
 
-            if (_executor is InteractiveExecutor executor)
-            {
-                InteractiveExecutorState state = (InteractiveExecutorState)executor.GetStateData();
-                prompt = state.IsPromptRun
-                    ? HistoryTransform.HistoryToText(History)
-                    : HistoryTransform.HistoryToText(HistoryTransform.TextToHistory(AuthorRole.User, prompt));
-            }
+        History.Messages[index] = newMessage;
+
+        // Remove all message after the new message
+        History.Messages.RemoveRange(index + 1, History.Messages.Count - index - 1);
+
+        return this;
+    }
 
-            StringBuilder sb = new();
+    /// <summary>
+    /// Chat with the model.
+    /// </summary>
+    /// <param name="message"></param>
+    /// <param name="inferenceParams"></param>
+    /// <param name="applyInputTransformPipeline"></param>
+    /// <param name="cancellationToken"></param>
+    /// <returns></returns>
+    /// <exception cref="ArgumentException"></exception>
+    public async IAsyncEnumerable<string> ChatAsync(
+        ChatHistory.Message message,
+        bool applyInputTransformPipeline,
+        IInferenceParams? inferenceParams = null,
+        [EnumeratorCancellation] CancellationToken cancellationToken = default)
+    {
+        // The message must be a user message
+        if (message.AuthorRole != AuthorRole.User)
+        {
+            throw new ArgumentException("Message must be a user message", nameof(message));
+        }
 
-            await foreach (var textToken in ChatAsyncInternal(prompt, inferenceParams, cancellationToken))
+        // Apply input transform pipeline
+        if (applyInputTransformPipeline)
+        {
+            foreach (var inputTransform in InputTransformPipeline)
             {
-                yield return textToken;
-                sb.Append(textToken);
+                message.Content = inputTransform.Transform(message.Content);
             }
+        }
 
-            string assistantMessage = sb.ToString();
+        // Add the user's message to the history
+        AddUserMessage(message.Content);
+
+        // Prepare prompt variable
+        string prompt;
+
+        // Check if the session history was restored from a previous session
+        // or added as part of new chat session history.
+        InteractiveExecutorState state = (InteractiveExecutorState)((StatefulExecutorBase)Executor).GetStateData();
+
+        // If "IsPromptRun" is true, the session was newly started.
+        if (state.IsPromptRun)
+        {
+            // If the session history was added as part of new chat session history,
+            // convert the complete history includsing system message and manually added history
+            // to a prompt that adhere to the prompt template specified in the HistoryTransform class implementation.
+            prompt = HistoryTransform.HistoryToText(History);
+        }
+        else
+        {
+            // If the session was restored from a previous session,
+            // convert only the current message to the prompt with the prompt template
+            // specified in the HistoryTransform class implementation that is provided.
+            ChatHistory singleMessageHistory = HistoryTransform.TextToHistory(message.AuthorRole, message.Content);
+            prompt = HistoryTransform.HistoryToText(singleMessageHistory);
+        }
+
+        string assistantMessage = string.Empty;
+
+        await foreach (
+            string textToken
+            in ChatAsyncInternal(
+                prompt,
+                inferenceParams,
+                cancellationToken))
+        {
+            assistantMessage += textToken;
+            yield return textToken;
+        }
 
-            // Remove end tokens from the assistant message
-            // if defined in inferenceParams.AntiPrompts.
-            // We only want the response that was generated and not tokens
-            // that are delimiting the beginning or end of the response.
-            if (inferenceParams?.AntiPrompts != null)
+        // Add the assistant message to the history
+        AddAssistantMessage(assistantMessage);
+    }
+
+    /// <summary>
+    /// Chat with the model.
+    /// </summary>
+    /// <param name="message"></param>
+    /// <param name="inferenceParams"></param>
+    /// <param name="cancellationToken"></param>
+    /// <returns></returns>
+    public IAsyncEnumerable<string> ChatAsync(
+        ChatHistory.Message message,
+        IInferenceParams? inferenceParams = null,
+        CancellationToken cancellationToken = default)
+    {
+        return ChatAsync(
+            message,
+            applyInputTransformPipeline: true,
+            inferenceParams,
+            cancellationToken);
+    }
+
+    /// <summary>
+    /// Chat with the model.
+    /// </summary>
+    /// <param name="history"></param>
+    /// <param name="applyInputTransformPipeline"></param>
+    /// <param name="inferenceParams"></param>
+    /// <param name="cancellationToken"></param>
+    /// <returns></returns>
+    /// <exception cref="ArgumentException"></exception>
+    public IAsyncEnumerable<string> ChatAsync(
+        ChatHistory history,
+        bool applyInputTransformPipeline,
+        IInferenceParams? inferenceParams = null,
+        CancellationToken cancellationToken = default)
+    {
+        ChatHistory.Message lastMessage = history.Messages.LastOrDefault()
+            ?? throw new ArgumentException("History must contain at least one message", nameof(history));
+
+        foreach (
+            ChatHistory.Message message
+            in history.Messages.Take(history.Messages.Count - 1))
+        {
+            // Apply input transform pipeline
+            if (applyInputTransformPipeline
+                && message.AuthorRole == AuthorRole.User)
             {
-                foreach (var stopToken in inferenceParams.AntiPrompts)
+                foreach (
+                    var inputTransform
+                    in InputTransformPipeline)
                 {
-                    assistantMessage = assistantMessage.Replace(stopToken, "").Trim();
+                    message.Content = inputTransform.Transform(message.Content);
                 }
             }
 
-            History.Messages.Add(new ChatHistory.Message(AuthorRole.Assistant, assistantMessage));
+            AddMessage(message);
         }
 
-        /// <summary>
-        /// Generates a response for a given chat history. This method does not manage history state for the user.
-        /// If you want to e.g. truncate the history of a session to fit into the model's context window,
-        /// use this method and pass the truncated history to it. If you don't need this control, use the other
-        /// overload of this method that accepts a user prompt instead.
-        /// </summary>
-        /// <param name="history"></param>
-        /// <param name="inferenceParams"></param>
-        /// <param name="cancellationToken"></param>
-        /// <returns>Returns generated text of the assistant message.</returns>
-        public async IAsyncEnumerable<string> ChatAsync(ChatHistory history, IInferenceParams? inferenceParams = null, [EnumeratorCancellation] CancellationToken cancellationToken = default)
+        return ChatAsync(
+            lastMessage,
+            applyInputTransformPipeline,
+            inferenceParams,
+            cancellationToken);
+    }
+
+    /// <summary>
+    /// Chat with the model.
+    /// </summary>
+    /// <param name="history"></param>
+    /// <param name="inferenceParams"></param>
+    /// <param name="cancellationToken"></param>
+    /// <returns></returns>
+    public IAsyncEnumerable<string> ChatAsync(
+        ChatHistory history,
+        IInferenceParams? inferenceParams = null,
+        CancellationToken cancellationToken = default)
+    {
+        return ChatAsync(
+            history,
+            applyInputTransformPipeline: true,
+            inferenceParams,
+            cancellationToken);
+    }
+
+    /// <summary>
+    /// Regenerate the last assistant message.
+    /// </summary>
+    /// <param name="inferenceParams"></param>
+    /// <param name="cancellationToken"></param>
+    /// <returns></returns>
+    /// <exception cref="InvalidOperationException"></exception>
+    public async IAsyncEnumerable<string> RegenerateAssistantMessageAsync(
+        InferenceParams? inferenceParams = null,
+        [EnumeratorCancellation] CancellationToken cancellationToken = default)
+    {
+        // Make sure the last message is an assistant message (reponse from the LLM).
+        ChatHistory.Message? lastAssistantMessage = History.Messages.LastOrDefault();
+
+        if (lastAssistantMessage is null
+            || lastAssistantMessage.AuthorRole != AuthorRole.Assistant)
         {
-            if (history.Messages.Count == 0)
-            {
-                throw new ArgumentException("History must contain at least one message.");
-            }
+            throw new InvalidOperationException("Last message must be an assistant message");
+        }
 
-            string prompt;
-            if (_executor is InteractiveExecutor executor)
-            {
-                InteractiveExecutorState state = (InteractiveExecutorState)executor.GetStateData();
+        // Remove the last assistant message from the history.
+        RemoveLastMessage();
 
-                if (state.IsPromptRun)
-                {
-                    prompt = HistoryTransform.HistoryToText(History);
-                }
-                else
-                {
-                    ChatHistory.Message lastMessage = history.Messages.Last();
-                    prompt = HistoryTransform.HistoryToText(HistoryTransform.TextToHistory(lastMessage.AuthorRole, lastMessage.Content));
-                }
-            }
-            else
-            {
-                ChatHistory.Message lastMessage = history.Messages.Last();
-                prompt = HistoryTransform.HistoryToText(HistoryTransform.TextToHistory(lastMessage.AuthorRole, lastMessage.Content));
-            }
+        // Get the last user message.
+        ChatHistory.Message? lastUserMessage = History.Messages.LastOrDefault();
 
-            await foreach (var textToken in ChatAsyncInternal(prompt, inferenceParams, cancellationToken))
-            {
-                yield return textToken;
-            }
+        if (lastUserMessage is null
+            || lastUserMessage.AuthorRole != AuthorRole.User)
+        {
+            throw new InvalidOperationException("Last message must be a user message");
         }
 
-        private async IAsyncEnumerable<string> ChatAsyncInternal(string prompt, IInferenceParams? inferenceParams = null, [EnumeratorCancellation] CancellationToken cancellationToken = default)
+        // Remove the last user message from the history.
+        RemoveLastMessage();
+
+        // Regenerate the assistant message.
+        await foreach (
+            string textToken
+            in ChatAsync(
+                lastUserMessage,
+                applyInputTransformPipeline: false,
+                inferenceParams,
+                cancellationToken))
         {
-            var results = _executor.InferAsync(prompt, inferenceParams, cancellationToken);
-            await foreach (var textToken in OutputTransform.TransformAsync(results).WithCancellation(cancellationToken))
-            {
-                yield return textToken;
-            }
+            yield return textToken;
+        }
+    }
+
+    private async IAsyncEnumerable<string> ChatAsyncInternal(
+        string prompt,
+        IInferenceParams? inferenceParams = null,
+        [EnumeratorCancellation] CancellationToken cancellationToken = default)
+    {
+        var results = Executor.InferAsync(prompt, inferenceParams, cancellationToken);
+
+        await foreach (
+            string textToken
+            in OutputTransform
+                .TransformAsync(results)
+                .WithCancellation(cancellationToken))
+        {
+            yield return textToken;
         }
     }
-}
\ No newline at end of file
+}
diff --git a/LLama/Common/ChatHistory.cs b/LLama/Common/ChatHistory.cs
index 7224b314..3f038874 100644
--- a/LLama/Common/ChatHistory.cs
+++ b/LLama/Common/ChatHistory.cs
@@ -1,4 +1,7 @@
 using System.Collections.Generic;
+using System.IO;
+using System.Text.Json;
+using System.Text.Json.Serialization;
 
 namespace LLama.Common
 {
@@ -43,11 +46,14 @@ namespace LLama.Common
             /// <summary>
             /// Role of the message author, e.g. user/assistant/system
             /// </summary>
+            [JsonConverter(typeof(JsonStringEnumConverter))]
+            [JsonPropertyName("author_role")]
             public AuthorRole AuthorRole { get; set; }
 
             /// <summary>
             /// Message content
             /// </summary>
+            [JsonPropertyName("content")]
             public string Content { get; set; }
 
             /// <summary>
@@ -65,15 +71,14 @@ namespace LLama.Common
         /// <summary>
         /// List of messages in the chat
         /// </summary>
-        public List<Message> Messages { get; }
+        [JsonPropertyName("messages")]
+        public List<Message> Messages { get; set; } = new();
 
         /// <summary>
         /// Create a new instance of the chat content class
         /// </summary>
-        public ChatHistory()
-        {
-            this.Messages = new List<Message>();
-        }
+        [JsonConstructor]
+        public ChatHistory() { }
 
         /// <summary>
         /// Add a message to the chat history
@@ -84,6 +89,29 @@ namespace LLama.Common
         {
             this.Messages.Add(new Message(authorRole, content));
         }
-    }
 
+        /// <summary>
+        /// Serialize the chat history to JSON
+        /// </summary>
+        /// <returns></returns>
+        public string ToJson()
+        {
+            return JsonSerializer.Serialize(
+                this,
+                new JsonSerializerOptions()
+                {
+                    WriteIndented = true
+                });
+        }
+
+        /// <summary>
+        /// Deserialize a chat history from JSON
+        /// </summary>
+        /// <param name="json"></param>
+        /// <returns></returns>
+        public static ChatHistory? FromJson(string json)
+        {
+            return JsonSerializer.Deserialize<ChatHistory>(json);
+        }
+    }
 }