diff --git a/scribe/lib/scribe/ai/data/datasource/ai_datasource.dart b/scribe/lib/scribe/ai/data/datasource/ai_datasource.dart
index 73af09b4d..ef60dc6ab 100644
--- a/scribe/lib/scribe/ai/data/datasource/ai_datasource.dart
+++ b/scribe/lib/scribe/ai/data/datasource/ai_datasource.dart
@@ -1,5 +1,6 @@
+import 'package:scribe/scribe/ai/data/model/ai_message.dart';
 import 'package:scribe/scribe/ai/domain/model/ai_response.dart';
 
 abstract class AIDataSource {
-  Future<AIResponse> generateMessage(String prompt);
+  Future<AIResponse> generateMessage(List<AIMessage> messages);
 }
diff --git a/scribe/lib/scribe/ai/data/datasource_impl/ai_datasource_impl.dart b/scribe/lib/scribe/ai/data/datasource_impl/ai_datasource_impl.dart
index 7ff7b02e7..d8fbfa9c6 100644
--- a/scribe/lib/scribe/ai/data/datasource_impl/ai_datasource_impl.dart
+++ b/scribe/lib/scribe/ai/data/datasource_impl/ai_datasource_impl.dart
@@ -1,5 +1,6 @@
 import 'package:dio/dio.dart';
 import 'package:scribe/scribe/ai/data/datasource/ai_datasource.dart';
+import 'package:scribe/scribe/ai/data/model/ai_message.dart';
 import 'package:scribe/scribe/ai/data/network/ai_api.dart';
 import 'package:scribe/scribe/ai/domain/model/ai_response.dart';
 
@@ -9,9 +10,9 @@ class AIDataSourceImpl implements AIDataSource {
   AIDataSourceImpl(this._aiApi);
 
   @override
-  Future<AIResponse> generateMessage(String prompt) async {
+  Future<AIResponse> generateMessage(List<AIMessage> messages) async {
     try {
-      final apiResponse = await _aiApi.generateMessage(prompt);
+      final apiResponse = await _aiApi.generateMessage(messages);
       return AIResponse(result: apiResponse.content);
     } on DioException catch (e) {
       throw Exception('Failed to generate AI text: ${e.message}');
diff --git a/scribe/lib/scribe/ai/data/model/ai_message.dart b/scribe/lib/scribe/ai/data/model/ai_message.dart
index eb8e6d571..e4cedee4e 100644
--- a/scribe/lib/scribe/ai/data/model/ai_message.dart
+++ b/scribe/lib/scribe/ai/data/model/ai_message.dart
@@ -5,6 +5,7 @@ part 'ai_message.g.dart';
 @JsonSerializable()
 class AIMessage {
   static const String aiUserRole = 'user';
+  static const String aiSystemRole = 'system';
 
   final String role;
   final String content;
@@ -23,4 +24,9 @@ class AIMessage {
         role: aiUserRole,
         content: content,
       );
+
+  factory AIMessage.ofSystem(String content) => AIMessage(
+        role: aiSystemRole,
+        content: content,
+      );
 }
diff --git a/scribe/lib/scribe/ai/data/network/ai_api.dart b/scribe/lib/scribe/ai/data/network/ai_api.dart
index 374effbae..d972e5dfe 100644
--- a/scribe/lib/scribe/ai/data/network/ai_api.dart
+++ b/scribe/lib/scribe/ai/data/network/ai_api.dart
@@ -9,8 +9,8 @@ class AIApi {
 
   AIApi(this._dioClient, this.aiEndpoint);
 
-  Future<AIApiResponse> generateMessage(String prompt) async {
-    final aiRequest = _generateRequest(prompt);
+  Future<AIApiResponse> generateMessage(List<AIMessage> messages) async {
+    final aiRequest = AIAPIRequest(messages: messages);
 
     final response = await _dioClient.post(
       aiEndpoint,
@@ -20,8 +20,4 @@ class AIApi {
 
     return AIApiResponse.fromJson(response);
   }
-
-  AIAPIRequest _generateRequest(String prompt) {
-    return AIAPIRequest(messages: [AIMessage.ofUser(prompt)]);
-  }
 }
diff --git a/scribe/lib/scribe/ai/data/repository/ai_repository_impl.dart b/scribe/lib/scribe/ai/data/repository/ai_repository_impl.dart
index f3d6115f1..68200d42f 100644
--- a/scribe/lib/scribe/ai/data/repository/ai_repository_impl.dart
+++ b/scribe/lib/scribe/ai/data/repository/ai_repository_impl.dart
@@ -1,4 +1,5 @@
 import 'package:scribe/scribe/ai/data/datasource/ai_datasource.dart';
+import 'package:scribe/scribe/ai/data/model/ai_message.dart';
 import 'package:scribe/scribe/ai/domain/model/ai_response.dart';
 import 'package:scribe/scribe/ai/domain/repository/ai_scribe_repository.dart';
 
@@ -8,7 +9,7 @@ class AIScribeRepositoryImpl implements AIScribeRepository {
   AIScribeRepositoryImpl(this._aiDataSource);
 
   @override
-  Future<AIResponse> generateMessage(String prompt) {
-    return _aiDataSource.generateMessage(prompt);
+  Future<AIResponse> generateMessage(List<AIMessage> messages) {
+    return _aiDataSource.generateMessage(messages);
   }
 }
diff --git a/scribe/lib/scribe/ai/domain/constants/ai_prompts.dart b/scribe/lib/scribe/ai/domain/constants/ai_prompts.dart
index a0eafc2ed..73b934695 100644
--- a/scribe/lib/scribe/ai/domain/constants/ai_prompts.dart
+++ b/scribe/lib/scribe/ai/domain/constants/ai_prompts.dart
@@ -1,3 +1,4 @@
+import 'package:scribe/scribe/ai/data/model/ai_message.dart';
 import 'package:scribe/scribe/ai/presentation/model/ai_action.dart';
 import 'package:scribe/scribe/ai/presentation/model/ai_scribe_menu_action.dart';
 
@@ -8,8 +9,8 @@ class AIPrompts {
   static const _doNotAddInfoPrompt =
       "Do not add any extra information or interpret anything beyond the explicit task.";
 
-  static String buildPrompt(AIAction action, String? text) {
-    return switch (action) {
+  static List<AIMessage> buildPrompt(AIAction action, String? text) {
+    final prompt =  switch (action) {
       PredefinedAction(action: final menuAction) =>
       text?.trim().isNotEmpty == true
           ? buildPredefinedPrompt(menuAction, text!)
@@ -17,6 +18,10 @@ class AIPrompts {
       CustomPromptAction(prompt: final customPrompt) =>
         buildCustomPrompt(customPrompt, text),
     };
+
+    final message = [AIMessage.ofUser(prompt)];
+
+    return message;
   }
 
   static String buildPredefinedPrompt(AIScribeMenuAction action, String text) {
diff --git a/scribe/lib/scribe/ai/domain/repository/ai_scribe_repository.dart b/scribe/lib/scribe/ai/domain/repository/ai_scribe_repository.dart
index 2412bf758..3f603a932 100644
--- a/scribe/lib/scribe/ai/domain/repository/ai_scribe_repository.dart
+++ b/scribe/lib/scribe/ai/domain/repository/ai_scribe_repository.dart
@@ -1,5 +1,6 @@
+import 'package:scribe/scribe/ai/data/model/ai_message.dart';
 import 'package:scribe/scribe/ai/domain/model/ai_response.dart';
 
 abstract class AIScribeRepository {
-  Future<AIResponse> generateMessage(String prompt);
+  Future<AIResponse> generateMessage(List<AIMessage> messages);
 }