diff --git a/blueprints/conversation/__init__.py b/blueprints/conversation/__init__.py
index 13309c8..0eb932a 100644
--- a/blueprints/conversation/__init__.py
+++ b/blueprints/conversation/__init__.py
@@ -15,6 +15,7 @@ from quart_jwt_extended import (
 import blueprints.users.models
 from metrics import count_result, observe_response, time_response
 from utils.image_process import image_content_block
+from utils.strip_markdown import extract_agent_text
 from utils.image_upload import ImageValidationError, process_image
 from utils.s3_client import generate_presigned_url as s3_presigned_url
 from utils.s3_client import get_image as s3_get_image
@@ -171,7 +172,7 @@ async def query():
         }
 
         response = await main_agent.ainvoke(payload, config=agent_config)
-        message = response.get("messages", [])[-1].content
+        message = extract_agent_text(response.get("messages", [])[-1].content)
         await persist_agent_tool_messages(
             conversation, user, response.get("messages", [])
         )
diff --git a/blueprints/conversation/logic.py b/blueprints/conversation/logic.py
index 91f2e31..f17c0e9 100644
--- a/blueprints/conversation/logic.py
+++ b/blueprints/conversation/logic.py
@@ -54,6 +54,7 @@ async def add_message_to_conversation(
     speaker: str,
     user: blueprints.users.models.User,
     image_key: str | None = None,
+    message_handle: str | None = None,
 ) -> ConversationMessage:
     # Bump updated_at on every message so conversations sort by last activity.
     # `update_fields` bypasses the auto_now recompute, so set it explicitly.
@@ -72,6 +73,7 @@ async def add_message_to_conversation(
         speaker=speaker,
         conversation=conversation,
         image_key=image_key,
+        message_handle=message_handle,
     )
 
     return message
@@ -105,7 +107,9 @@ async def get_conversation_for_user(user: blueprints.users.models.User) -> Conve
 async def get_conversation_for_channel(
     user: blueprints.users.models.User, channel: str
 ) -> Conversation:
-    conversation = await Conversation.filter(user=user, channel=channel).first()
+    conversation = await (
+        Conversation.filter(user=user, channel=channel).order_by("-updated_at").first()
+    )
     if conversation is None:
         conversation = await Conversation.create(
             name=f"{user.username}'s {channel} chat", user=user, channel=channel
diff --git a/blueprints/conversation/models.py b/blueprints/conversation/models.py
index 0b1fd15..309bc84 100644
--- a/blueprints/conversation/models.py
+++ b/blueprints/conversation/models.py
@@ -37,6 +37,7 @@ class ConversationMessage(Model):
     created_at = fields.DatetimeField(auto_now_add=True)
     speaker = fields.CharEnumField(enum_type=Speaker, max_length=10)
     image_key = fields.CharField(max_length=512, null=True, default=None)
+    message_handle = fields.CharField(max_length=255, null=True, default=None)
 
     class Meta:
         table = "conversation_messages"
diff --git a/blueprints/imessage/__init__.py b/blueprints/imessage/__init__.py
index ba7cf4e..0852927 100644
--- a/blueprints/imessage/__init__.py
+++ b/blueprints/imessage/__init__.py
@@ -14,9 +14,10 @@ from blueprints.conversation.logic import (
     add_message_to_conversation,
     persist_agent_tool_messages,
 )
-from blueprints.conversation.models import Speaker
+from blueprints.conversation.models import Conversation, ConversationMessage, Speaker
 from blueprints.conversation.agents import main_agent
 from blueprints.conversation.memory import build_system_prompt_with_memories
+from utils.strip_markdown import extract_agent_text, strip_markdown
 
 imessage_blueprint = Blueprint("imessage_api", __name__, url_prefix="/api/imessage")
 
@@ -59,25 +60,60 @@ def _check_rate_limit(phone_number: str) -> bool:
     return True
 
 
-async def send_imessage(to_number: str, content: str) -> dict:
+async def send_imessage(
+    to_number: str,
+    content: str,
+    reply_to_handle: str | None = None,
+) -> dict:
     """Send an iMessage via SendBlue API."""
     from_number = os.getenv("SENDBLUE_FROM_NUMBER", "")
 
+    payload: dict = {
+        "number": to_number,
+        "from_number": from_number,
+        "content": content,
+    }
+    if reply_to_handle:
+        payload["reply_to"] = {"message_handle": reply_to_handle}
+
     async with httpx.AsyncClient() as client:
         resp = await client.post(
             f"{SENDBLUE_API_BASE}/api/send-message",
             headers=_get_sendblue_headers(),
-            json={
-                "number": to_number,
-                "from_number": from_number,
-                "content": content,
-            },
+            json=payload,
             timeout=30,
         )
         resp.raise_for_status()
         return resp.json()
 
 
+async def send_typing_indicator(
+    to_number: str,
+    state: str = "start",
+    max_duration_ms: int | None = None,
+) -> None:
+    """Send or stop a typing indicator. Errors are logged and swallowed."""
+    from_number = os.getenv("SENDBLUE_FROM_NUMBER", "")
+    payload: dict = {
+        "number": to_number,
+        "from_number": from_number,
+        "state": state,
+    }
+    if max_duration_ms is not None:
+        payload["max_duration_ms"] = max_duration_ms
+
+    try:
+        async with httpx.AsyncClient() as client:
+            await client.post(
+                f"{SENDBLUE_API_BASE}/api/send-typing-indicator",
+                headers=_get_sendblue_headers(),
+                json=payload,
+                timeout=10,
+            )
+    except Exception as e:
+        logger.warning(f"Failed to send typing indicator ({state}): {e}")
+
+
 def validate_sendblue_signature(f):
     """Decorator to validate the SendBlue webhook signing secret."""
 
@@ -114,6 +150,11 @@ async def webhook():
     media_url = data.get("media_url")
     is_outbound = data.get("is_outbound", False)
 
+    # Threading fields from SendBlue
+    inbound_handle = data.get("message_handle")
+    reply_to_handle = (data.get("reply_to") or {}).get("message_handle")
+    originator_handle = (data.get("thread_originator") or {}).get("message_handle")
+
     # Ignore outbound messages (our own replies echoed back)
     if is_outbound:
         return jsonify({"status": "ignored"}), 200
@@ -183,23 +224,73 @@ async def webhook():
         await send_imessage(from_number, "Sorry, this feature is restricted to admins.")
         return jsonify({"status": "forbidden"}), 200
 
-    # Get or create conversation
+    # /threads command — list recent iMessage conversations
+    if content.strip().lower() == "/threads":
+        threads = (
+            await Conversation.filter(user=user, channel="imessage")
+            .order_by("-updated_at")
+            .limit(5)
+        )
+        if not threads:
+            await send_imessage(from_number, "No threads found.")
+        else:
+            lines = ["Your recent threads (most recent first):"]
+            for i, t in enumerate(threads, 1):
+                updated = t.updated_at.strftime("%b %-d")
+                lines.append(f"{i}. {t.name} ({updated})")
+            lines.append("\nReply to any message to continue its thread.")
+            await send_imessage(from_number, "\n".join(lines))
+        return jsonify({"status": "ok"}), 200
+
+    # Determine conversation based on iMessage reply threading:
+    # - Reply to an existing message → continue that conversation
+    # - New standalone message → start a fresh conversation
     try:
-        conversation = await get_conversation_for_channel(user=user, channel="imessage")
+        if reply_to_handle:
+            lookup_handle = originator_handle or reply_to_handle
+            parent_msg = await ConversationMessage.get_or_none(
+                message_handle=lookup_handle,
+                conversation__user=user,
+                conversation__channel="imessage",
+            )
+            if parent_msg:
+                conversation = await Conversation.get(id=parent_msg.conversation_id)
+                logger.info(
+                    f"Continuing conversation {conversation.id} via reply to {lookup_handle!r}"
+                )
+            else:
+                # Handle not found (pre-migration messages) — fall back to most recent
+                logger.warning(
+                    f"Reply handle {lookup_handle!r} not in DB; falling back to most recent conversation"
+                )
+                conversation = await get_conversation_for_channel(
+                    user=user, channel="imessage"
+                )
+        else:
+            conversation = await Conversation.create(
+                name="New iMessage",
+                user=user,
+                channel="imessage",
+            )
+            logger.info(
+                f"New iMessage conversation {conversation.id} for {user.username}"
+            )
+
         await conversation.fetch_related("messages")
     except Exception as e:
-        logger.error(f"Failed to get conversation for user {user.username}: {e}")
+        logger.error(f"Failed to get/create conversation for {user.username}: {e}")
         await send_imessage(
             from_number, "Sorry, something went wrong. Please try again later."
         )
         return jsonify({"status": "error"}), 200
 
-    # Add user message to conversation
+    # Add user message (store the inbound handle for future reply lookups)
     await add_message_to_conversation(
         conversation=conversation,
         message=content,
         speaker="user",
         user=user,
+        message_handle=inbound_handle,
     )
 
     # Attach image directly to the agent request if present
@@ -216,7 +307,11 @@ async def webhook():
             logger.error(f"Failed to load iMessage image: {e}")
             content = f"{content or ''}\n\n[An image was sent but could not be loaded.]".strip()
 
+    # Show typing indicator for up to 2 minutes while the agent processes
+    await send_typing_indicator(from_number, state="start", max_duration_ms=120_000)
+
     # Build messages payload for LangChain agent
+    response_text = "Sorry, I'm having trouble thinking right now."
     try:
         messages = await conversation.messages.all()
         recent_messages = list(messages)[-20:]
@@ -244,25 +339,30 @@ async def webhook():
         response = await main_agent.ainvoke(
             {"messages": messages_payload}, config=agent_config
         )
-        response_text = response.get("messages", [])[-1].content
+        response_text = extract_agent_text(response.get("messages", [])[-1].content)
         await persist_agent_tool_messages(
             conversation, user, response.get("messages", [])
         )
 
     except Exception as e:
         logger.error(f"Error invoking agent: {e}")
-        response_text = "Sorry, I'm having trouble thinking right now."
+    finally:
+        await send_typing_indicator(from_number, state="stop")
+
+    # Send reply threaded under the user's inbound message
+    send_resp = await send_imessage(
+        from_number,
+        strip_markdown(response_text),
+        reply_to_handle=inbound_handle,
+    )
+    outbound_handle = (send_resp or {}).get("message_handle")
 
-    # Save and send response
     await add_message_to_conversation(
         conversation=conversation,
         message=response_text,
         speaker="simba",
         user=user,
+        message_handle=outbound_handle,
     )
 
-    from utils.strip_markdown import strip_markdown
-
-    await send_imessage(from_number, strip_markdown(response_text))
-
     return jsonify({"status": "ok"}), 200
diff --git a/blueprints/whatsapp/__init__.py b/blueprints/whatsapp/__init__.py
index 30faeea..e438eb4 100644
--- a/blueprints/whatsapp/__init__.py
+++ b/blueprints/whatsapp/__init__.py
@@ -16,6 +16,7 @@ from blueprints.conversation.logic import (
 from blueprints.conversation.models import Speaker
 from blueprints.conversation.agents import main_agent
 from blueprints.conversation.prompts import SIMBA_SYSTEM_PROMPT
+from utils.strip_markdown import extract_agent_text
 
 whatsapp_blueprint = Blueprint("whatsapp_api", __name__, url_prefix="/api/whatsapp")
 
@@ -198,7 +199,7 @@ async def webhook():
         # Invoke LangChain agent
         logger.info(f"Invoking LangChain agent with {len(messages_payload)} messages")
         response = await main_agent.ainvoke({"messages": messages_payload})
-        response_text = response.get("messages", [])[-1].content
+        response_text = extract_agent_text(response.get("messages", [])[-1].content)
         await persist_agent_tool_messages(
             conversation, user, response.get("messages", [])
         )
diff --git a/utils/strip_markdown.py b/utils/strip_markdown.py
index 8094d5a..2b73045 100644
--- a/utils/strip_markdown.py
+++ b/utils/strip_markdown.py
@@ -1,5 +1,26 @@
 import re
 
+_THINK_RE = re.compile(r"<think>.*?</think>", re.DOTALL)
+
+
+def extract_agent_text(content) -> str:
+    """Extract plain text from a LangChain AIMessage content.
+
+    Handles both str and list-of-blocks content (the latter occurs with some
+    tool-using or vision models), and strips <think>...</think> tokens emitted
+    by reasoning models like Qwen3.
+    """
+    if isinstance(content, list):
+        text = "".join(
+            block.get("text", "")
+            if isinstance(block, dict) and block.get("type") != "thinking"
+            else (str(block) if not isinstance(block, dict) else "")
+            for block in content
+        )
+    else:
+        text = str(content) if content is not None else ""
+    return _THINK_RE.sub("", text).strip()
+
 
 def strip_markdown(text: str) -> str:
     """Strip markdown formatting from text for plain-text channels like iMessage."""