diff --git a/app/database.py b/app/database.py
index e937541..3108be1 100644
--- a/app/database.py
+++ b/app/database.py
@@ -4,6 +4,7 @@ from datetime import datetime, timedelta
 from typing import Optional
 import uuid
 import sqlalchemy as sa
+from fastapi import Request
 from sqlalchemy.ext.asyncio import create_async_engine, AsyncSession
 from sqlalchemy.orm import sessionmaker, declarative_base
 from sqlalchemy import Column, String, DateTime, Boolean, ForeignKey, select
@@ -156,6 +157,6 @@ class ConversationManager:
                 print(f"Cleaned up {len(conv_ids)} old conversations")
 
 
-async def get_conversation_manager() -> ConversationManager:
-    """Dependency for FastAPI to get a ConversationManager instance."""
-    return ConversationManager(settings.db_url)
+async def get_conversation_manager(request: Request) -> ConversationManager:
+    """Dependency for FastAPI to get the singleton ConversationManager from app state."""
+    return request.app.state.db_manager
diff --git a/app/discord_bot.py b/app/discord_bot.py
index 0504c08..83f0e69 100644
--- a/app/discord_bot.py
+++ b/app/discord_bot.py
@@ -3,10 +3,8 @@
 import discord
 from discord import app_commands
 from discord.ext import commands
-import asyncio
 import aiohttp
 from typing import Optional
-import uuid
 
 from .config import settings
 
@@ -51,6 +49,9 @@ class StratChatbotBot(commands.Bot):
         parent_message_id: Optional[str] = None,
     ) -> dict:
         """Send a request to the FastAPI chat endpoint."""
+        if not self.session:
+            raise RuntimeError("Bot HTTP session not initialized")
+
         payload = {
             "message": message,
             "user_id": user_id,
@@ -76,6 +77,8 @@ bot = StratChatbotBot()
 @bot.event
 async def on_ready():
     """Called when the bot is ready."""
+    if not bot.user:
+        return
     print(f"🤖 Bot logged in as {bot.user} (ID: {bot.user.id})")
     print("Ready to answer Strat-O-Matic rules questions!")
 
@@ -123,10 +126,9 @@ async def ask_command(interaction: discord.Interaction, question: str):
                 inline=False,
             )
 
-        # Add conversation ID for follow-ups
+        # Add conversation ID for follow-ups (full UUID so replies can be threaded)
         embed.set_footer(
-            text=f"Conversation: {result['conversation_id'][:8]}... "
-            f"| Reply to ask a follow-up"
+            text=f"conv:{result['conversation_id']} | Reply to ask a follow-up"
         )
 
         await interaction.followup.send(embed=embed)
@@ -149,7 +151,7 @@ async def on_message(message: discord.Message):
         return
 
     # Only handle replies to the bot's messages
-    if not message.reference:
+    if not message.reference or message.reference.message_id is None:
         return
 
     referenced = await message.channel.fetch_message(message.reference.message_id)
@@ -168,31 +170,36 @@ async def on_message(message: discord.Message):
         return
 
     footer_text = embed.footer.text or ""
-    if "Conversation:" not in footer_text:
+    if "conv:" not in footer_text:
         await message.reply(
             "❓ Could not determine conversation. Use `/ask` to start fresh.",
             mention_author=True,
         )
         return
 
-    # Extract conversation ID (rough parsing)
+    # Extract full conversation UUID from "conv:<uuid> | ..." format
     try:
-        conv_id = footer_text.split("Conversation:")[1].split("...")[0].strip()
-        conversation_id = footer_text.split("Conversation:")[1].split(" ")[0].strip()
-    except:
-        conversation_id = None
+        conversation_id = footer_text.split("conv:")[1].split(" ")[0].strip()
+    except (IndexError, AttributeError):
+        await message.reply(
+            "❓ Could not parse conversation ID. Use `/ask` to start fresh.",
+            mention_author=True,
+        )
+        return
 
     # Get parent message ID (the original answer message)
     parent_message_id = str(referenced.id)
 
-    # Forward to API
-    await message.reply("🔍 Looking into that follow-up...", mention_author=True)
+    # Send a loading placeholder and replace it with the real answer when ready
+    loading_msg = await message.reply(
+        "🔍 Looking into that follow-up...", mention_author=True
+    )
 
     try:
         result = await bot.query_chat_api(
             message=message.content,
             user_id=str(message.author.id),
-            channel_id=str(message.channel_id),
+            channel_id=str(message.channel.id),
             conversation_id=conversation_id,
             parent_message_id=parent_message_id,
         )
@@ -213,19 +220,25 @@ async def on_message(message: discord.Message):
         if result.get("confidence", 0.0) < 0.4:
             response_embed.add_field(
                 name="⚠️ Confidence",
-                value=f"Low - Human review requested",
+                value="Low - Human review requested",
                 inline=False,
             )
 
-        await message.reply(embed=response_embed, mention_author=True)
+        # Carry the conversation ID forward so further replies stay in the same thread
+        response_embed.set_footer(
+            text=f"conv:{result['conversation_id']} | Reply to ask a follow-up"
+        )
+
+        await loading_msg.edit(content=None, embed=response_embed)
 
     except Exception as e:
-        await message.reply(
+        await loading_msg.edit(
+            content=None,
             embed=discord.Embed(
                 title="❌ Error",
                 description=f"Failed to process follow-up: {str(e)}",
                 color=discord.Color.red(),
-            )
+            ),
         )
 
 
diff --git a/app/gitea.py b/app/gitea.py
index 9d72622..a9522f2 100644
--- a/app/gitea.py
+++ b/app/gitea.py
@@ -19,17 +19,6 @@ class GiteaClient:
             "Content-Type": "application/json",
             "Accept": "application/json",
         }
-        self._client: Optional[httpx.AsyncClient] = None
-
-    async def __aenter__(self):
-        """Async context manager entry."""
-        self._client = httpx.AsyncClient(timeout=30.0)
-        return self
-
-    async def __aexit__(self, exc_type, exc_val, exc_tb):
-        """Async context manager exit."""
-        if self._client:
-            await self._client.aclose()
 
     async def create_issue(
         self,
@@ -39,12 +28,9 @@ class GiteaClient:
         assignee: Optional[str] = None,
     ) -> dict:
         """Create a new issue in the configured repository."""
-        if not self._client:
-            raise RuntimeError("GiteaClient must be used as async context manager")
-
         url = f"{self.base_url}/repos/{self.owner}/{self.repo}/issues"
 
-        payload = {"title": title, "body": body}
+        payload: dict = {"title": title, "body": body}
 
         if labels:
             payload["labels"] = labels
@@ -52,7 +38,8 @@ class GiteaClient:
         if assignee:
             payload["assignee"] = assignee
 
-        response = await self._client.post(url, headers=self.headers, json=payload)
+        async with httpx.AsyncClient(timeout=30.0) as client:
+            response = await client.post(url, headers=self.headers, json=payload)
 
         if response.status_code not in (200, 201):
             error_detail = response.text
diff --git a/app/vector_store.py b/app/vector_store.py
index 3fc85f7..ddb9b9e 100644
--- a/app/vector_store.py
+++ b/app/vector_store.py
@@ -85,7 +85,9 @@ class VectorStore:
             for i in range(len(results["documents"][0])):
                 metadata = results["metadatas"][0][i]
                 distance = results["distances"][0][i]
-                similarity = 1 - distance  # Convert cosine distance to similarity
+                similarity = max(
+                    0.0, min(1.0, 1 - distance)
+                )  # Clamp to [0, 1]: cosine distance ranges 0–2
 
                 search_results.append(
                     RuleSearchResult(