diff --git a/agent_service/agents/master_agent.py b/agent_service/agents/master_agent.py
index c8a8334..952b5d3 100644
--- a/agent_service/agents/master_agent.py
+++ b/agent_service/agents/master_agent.py
@@ -80,6 +80,11 @@ class MasterAgent:
         t0 = time.monotonic()
         await self._log_directive_start(directive_id, user_id, channel_id, message)
         try:
+            # Persist the user message FIRST so it's part of context on every
+            # branch (clarification, access-denied, happy path). Without this,
+            # clarification turns lose the original question and the bot can't
+            # connect follow-up replies to the in-flight conversation.
+            await self._memory.append_message(user_id, 'user', message, directive_id)
             context = await self._build_context(user_id, message)
             intent = await self._classify_intent(context, message)
             if intent.needs_clarification:
@@ -226,7 +231,8 @@ class MasterAgent:
         return resp.content
 
     async def _update_memory(self, user_id, message, response, reports, directive_id):
-        await self._memory.append_message(user_id, 'user', message, directive_id)
+        # User message is persisted at the top of handle_message — only save
+        # the assistant reply here.
         await self._memory.append_message(user_id, 'assistant', response, directive_id)
         for report in reports:
             if report.data: