Nestbot AI Direct message implementation

backend/apps/slack/MANIFEST.yaml

@@ -133,6 +133,7 @@ settings:
       - app_mention
       - member_joined_channel
       - message.channels
+      - message.im
       - team_join
   interactivity:
     is_enabled: true

backend/apps/slack/common/handlers/ai.py

@@ -6,6 +6,8 @@
 
 from apps.ai.agent.tools.rag.rag_tool import RagTool
 from apps.slack.blocks import markdown
+from apps.slack.constants import CONVERSATION_CONTEXT_LIMIT
+from apps.slack.models import Conversation, Workspace
 
 logger = logging.getLogger(__name__)
 
@@ -46,6 +48,62 @@ def process_ai_query(query: str) -> str | None:
     return rag_tool.query(question=query)
 
 
+def get_dm_blocks(query: str, workspace_id: str, channel_id: str) -> list[dict]:
+    """Get AI response blocks for DM with conversation context.
+
+    Args:
+        query (str): The user's question.
+        workspace_id (str): Slack workspace ID.
+        channel_id (str): Slack channel ID for the DM.
+
+    Returns:
+        list: A list of Slack blocks representing the AI response.
+
+    """
+    ai_response = process_dm_ai_query(query.strip(), workspace_id, channel_id)
+
+    if ai_response:
+        return [markdown(ai_response)]
+    return get_error_blocks()
+
+
+def process_dm_ai_query(query: str, workspace_id: str, channel_id: str) -> str | None:
+    """Process the AI query with DM conversation context.
+
+    Args:
+        query (str): The user's question.
+        workspace_id (str): Slack workspace ID.
+        channel_id (str): Slack channel ID for the DM.
+
+    Returns:
+        str | None: The AI response or None if error occurred.
+
+    """
+    try:
+        workspace = Workspace.objects.get(slack_workspace_id=workspace_id)
+        conversation = Conversation.objects.get(slack_channel_id=channel_id, workspace=workspace)
+    except (Workspace.DoesNotExist, Conversation.DoesNotExist):
+        logger.exception("Workspace or conversation not found for DM processing")
+        return None
+
+    context = conversation.get_context(conversation_context_limit=CONVERSATION_CONTEXT_LIMIT)
+
+    rag_tool = RagTool(
+        chat_model="gpt-4o",
+        embedding_model="text-embedding-3-small",
+    )
+
+    if context:
+        enhanced_query = f"Conversation context:\n{context}\n\nCurrent question: {query}"
+    else:
+        enhanced_query = query
+
+    response = rag_tool.query(question=enhanced_query)
+    conversation.add_to_context(query, response)
+
+    return response
+
+
 def get_error_blocks() -> list[dict]:
     """Get error response blocks.
 

backend/apps/slack/constants.py

@@ -2,6 +2,7 @@
 
 from apps.common.constants import NL
 
+CONVERSATION_CONTEXT_LIMIT = 20
 NEST_BOT_NAME = "NestBot"
 
 OWASP_APPSEC_CHANNEL_ID = "#C0F7D6DFH"

backend/apps/slack/events/message_posted.py

@@ -1,21 +1,22 @@
-"""Slack message event template."""
+"""Slack message event handler for OWASP NestBot."""
 
 import logging
 from datetime import timedelta
 
 import django_rq
 
 from apps.ai.common.constants import QUEUE_RESPONSE_TIME_MINUTES
+from apps.slack.common.handlers.ai import get_dm_blocks
 from apps.slack.common.question_detector import QuestionDetector
 from apps.slack.events.event import EventBase
-from apps.slack.models import Conversation, Member, Message
+from apps.slack.models import Conversation, Member, Message, Workspace
 from apps.slack.services.message_auto_reply import generate_ai_reply_if_unanswered
 
 logger = logging.getLogger(__name__)
 
 
 class MessagePosted(EventBase):
-    """Handles new messages posted in channels."""
+    """Handles new messages posted in channels or direct messages."""
 
     event_type = "message"
 
@@ -24,25 +25,30 @@ def __init__(self):
         self.question_detector = QuestionDetector()
 
     def handle_event(self, event, client):
-        """Handle an incoming message event."""
+        """Handle incoming Slack message events."""
         if event.get("subtype") or event.get("bot_id"):
-            logger.info("Ignored message due to subtype, bot_id, or thread_ts.")
+            logger.info("Ignored message due to subtype or bot_id.")
+            return
+
+        channel_id = event.get("channel")
+        user_id = event.get("user")
+        text = event.get("text", "")
+        channel_type = event.get("channel_type")
+
+        if channel_type == "im":
+            self.handle_dm(event, client, channel_id, user_id, text)
             return
 
         if event.get("thread_ts"):
             try:
                 Message.objects.filter(
                     slack_message_id=event.get("thread_ts"),
-                    conversation__slack_channel_id=event.get("channel"),
+                    conversation__slack_channel_id=channel_id,
                 ).update(has_replies=True)
             except Message.DoesNotExist:
                 logger.warning("Thread message not found.")
             return
 
-        channel_id = event.get("channel")
-        user_id = event.get("user")
-        text = event.get("text", "")
-
         try:
             conversation = Conversation.objects.get(
                 slack_channel_id=channel_id,
@@ -71,3 +77,46 @@ def handle_event(self, event, client):
             generate_ai_reply_if_unanswered,
             message.id,
         )
+
+    def handle_dm(self, event, client, channel_id, user_id, text):
+        """Handle direct messages with NestBot (DMs)."""
+        workspace_id = event.get("team")
+        channel_info = client.conversations_info(channel=channel_id)
+
+        try:
+            workspace = Workspace.objects.get(slack_workspace_id=workspace_id)
+        except Workspace.DoesNotExist:
+            logger.exception("Workspace not found for DM.")
+            return
+
+        Conversation.update_data(channel_info["channel"], workspace)
+
+        try:
+            Member.objects.get(slack_user_id=user_id, workspace=workspace)
+        except Member.DoesNotExist:
+            user_info = client.users_info(user=user_id)
+            Member.update_data(user_info["user"], workspace, save=True)
+            logger.info("Created new member for DM")
+
+        thread_ts = event.get("thread_ts")
+
+        try:
+            response_blocks = get_dm_blocks(text, workspace_id, channel_id)
+            if response_blocks:
+                client.chat_postMessage(
+                    channel=channel_id,
+                    blocks=response_blocks,
+                    text=text,
+                    thread_ts=thread_ts,
+                )
+
+        except Exception:
+            logger.exception("Error processing DM")
+            client.chat_postMessage(
+                channel=channel_id,
+                text=(
+                    "I'm sorry, I'm having trouble processing your message right now. "
+                    "Please try again later."
+                ),
+                thread_ts=thread_ts,
+            )

backend/apps/slack/migrations/0020_conversation_conversation_context.py

@@ -0,0 +1,17 @@
+# Generated by Django 5.2.6 on 2025-10-08 07:21
+
+from django.db import migrations, models
+
+
+class Migration(migrations.Migration):
+    dependencies = [
+        ("slack", "0019_conversation_is_nest_bot_assistant_enabled"),
+    ]
+
+    operations = [
+        migrations.AddField(
+            model_name="conversation",
+            name="conversation_context",
+            field=models.TextField(blank=True, verbose_name="Conversation context"),
+        ),
+    ]

backend/apps/slack/models/conversation.py

@@ -42,6 +42,7 @@ class Meta:
 
     # Additional attributes.
     sync_messages = models.BooleanField(verbose_name="Sync messages", default=False)
+    conversation_context = models.TextField(blank=True, verbose_name="Conversation context")
 
     def __str__(self):
         """Channel human readable representation."""
@@ -105,3 +106,43 @@ def update_data(conversation_data, workspace, *, save=True):
             conversation.save()
 
         return conversation
+
+    def add_to_context(self, user_message: str, bot_response: str | None = None) -> None:
+        """Add messages to the conversation context.
+
+        Args:
+            user_message: The user's message to add to context.
+            bot_response: The bot's response to add to context.
+
+        """
+        if not self.conversation_context:
+            self.conversation_context = ""
+
+        self.conversation_context = f"{self.conversation_context}{f'User: {user_message}\n'}"
+
+        if bot_response:
+            self.conversation_context = f"{self.conversation_context}{f'Bot: {bot_response}\n'}"
+
+        self.save(update_fields=["conversation_context"])
+
+    def get_context(self, conversation_context_limit: int | None = None) -> str:
+        """Get the conversation context.
+
+        Args:
+            conversation_context_limit: Optional limit on number of exchanges to return.
+
+        Returns:
+            The conversation context, potentially limited to recent exchanges.
+
+        """
+        if not self.conversation_context:
+            return ""
+
+        if conversation_context_limit is None:
+            return self.conversation_context
+
+        lines = self.conversation_context.strip().split("\n")
+        if len(lines) <= conversation_context_limit * 2:
+            return self.conversation_context
+
+        return "\n".join(lines[-(conversation_context_limit * 2) :])

backend/tests/apps/slack/events/message_posted_test.py

@@ -88,11 +88,17 @@ def test_handle_event_ignores_thread_messages(self, message_handler):
         client = Mock()
 
         with patch("apps.slack.events.message_posted.Message") as mock_message:
-            mock_message.DoesNotExist = Exception
-            mock_message.objects.get.side_effect = Exception("Message not found")
+            mock_filter = Mock()
+            mock_message.objects.filter.return_value = mock_filter
 
             message_handler.handle_event(event, client)
 
+            mock_message.objects.filter.assert_called_once_with(
+                slack_message_id=event.get("thread_ts"),
+                conversation__slack_channel_id=event.get("channel"),
+            )
+            mock_filter.update.assert_called_once_with(has_replies=True)
+
         client.chat_postMessage.assert_not_called()
 
     def test_handle_event_conversation_not_found(self, message_handler):
@@ -260,6 +266,7 @@ def test_handle_event_member_not_found(self, message_handler, conversation_mock)
             patch("apps.slack.events.message_posted.Conversation") as mock_conversation,
             patch("apps.slack.events.message_posted.Member") as mock_member,
             patch("apps.slack.events.message_posted.Message") as mock_message_model,
+            patch("apps.slack.events.message_posted.django_rq") as mock_django_rq,
         ):
             mock_conversation.objects.get.return_value = conversation_mock
 
@@ -273,19 +280,17 @@ def test_handle_event_member_not_found(self, message_handler, conversation_mock)
             mock_message.id = 1
             mock_message_model.update_data.return_value = mock_message
 
-            with (
-                patch.object(
-                    message_handler.question_detector,
-                    "is_owasp_question",
-                    return_value=True,
-                ),
-                patch("apps.slack.events.message_posted.django_rq") as mock_django_rq,
-            ):
-                mock_queue = Mock()
-                mock_django_rq.get_queue.return_value = mock_queue
+            mock_queue = Mock()
+            mock_django_rq.get_queue.return_value = mock_queue
 
+            with patch.object(
+                message_handler.question_detector,
+                "is_owasp_question",
+                return_value=True,
+            ):
                 message_handler.handle_event(event, client)
 
+                mock_member.update_data.assert_called_once()
                 mock_django_rq.get_queue.assert_called_once()
 
     def test_handle_event_empty_text(self, message_handler):