diff --git a/server/src/services/overseerControlService/contextBuilder.js b/server/src/services/overseerControlService/contextBuilder.js
index dec83a03..e09f6e22 100644
--- a/server/src/services/overseerControlService/contextBuilder.js
+++ b/server/src/services/overseerControlService/contextBuilder.js
@@ -26,21 +26,29 @@ function buildToolState({ mode, homeAssistantState, neatoState, liftState }) {
 }
 
 function buildConversation({ recentMessages, name }) {
-  const rows = [];
+  const messages = [];
   (recentMessages || []).forEach((entry) => {
     const text = String(entry?.text || '').trim();
     if (!text) return;
-    const who = entry?.system ? (entry?.nickname || name || 'Overseer') : (entry?.nickname || 'user');
-    rows.push(`${who}: ${text}`);
+    const isAssistant = Boolean(entry?.bot || entry?.system);
+    const nickname = String(entry?.nickname || (isAssistant ? name || 'Overseer' : 'user')).trim();
+    if (isAssistant) {
+      messages.push({ role: 'assistant', content: text });
+      return;
+    }
+    messages.push({ role: 'user', content: `${nickname}: ${text}` });
   });
-  return rows;
+  return messages;
 }
 
-function buildModelMessages({ systemPrompt, stateUpdate, transcriptRows, availableTools, blockedTools }) {
+function buildModelMessages({ systemPrompt, stateUpdate, conversationMessages, availableTools, blockedTools }) {
   const messages = [];
   messages.push({ role: 'system', content: systemPrompt });
   messages.push({ role: 'user', content: `STATE_UPDATE\n${stateUpdate}` });
-  transcriptRows.forEach((row) => messages.push({ role: 'user', content: row }));
+  (conversationMessages || []).forEach((message) => {
+    if (!message || !message.role || !message.content) return;
+    messages.push(message);
+  });
   messages.push({
     role: 'user',
     content: `available_tools:\n${availableTools.map((tool) => `- ${tool}`).join('\n') || '- none'}`,
diff --git a/server/src/services/overseerControlService/index.js b/server/src/services/overseerControlService/index.js
index 1b9470d5..68d4830b 100644
--- a/server/src/services/overseerControlService/index.js
+++ b/server/src/services/overseerControlService/index.js
@@ -144,18 +144,23 @@ async function runDecision(triggerReason) {
   const stateUpdate = toStateUpdate({ mode, homeAssistantState, neatoState, liftState, roster, triggerReason });
   const toolState = buildToolState({ mode, homeAssistantState, neatoState, liftState });
 
-  const human = getRecentMessages(MAX_CHAT_CONTEXT, { includeSystem: false });
-  const bots = getRecentMessages(100, { includeSystem: true }).filter((entry) => entry?.system).slice(-MAX_BOT_CONTEXT);
-  const transcriptRows = buildConversation({ recentMessages: [...human, ...bots].slice(-(MAX_CHAT_CONTEXT + MAX_BOT_CONTEXT)), name });
+  const recentConversation = getRecentMessages(MAX_CHAT_CONTEXT + MAX_BOT_CONTEXT, { includeSystem: true });
+  const conversationMessages = buildConversation({ recentMessages: recentConversation, name });
 
   const systemPrompt = await readPrompt();
-  const modelMessages = buildModelMessages({ systemPrompt, stateUpdate, transcriptRows, availableTools: toolState.available, blockedTools: toolState.blocked });
+  const modelMessages = buildModelMessages({
+    systemPrompt,
+    stateUpdate,
+    conversationMessages,
+    availableTools: toolState.available,
+    blockedTools: toolState.blocked,
+  });
 
   updateStatus({
     phase: 'awaiting_model',
     lastSystemPrompt: systemPrompt,
     lastStateUpdate: stateUpdate,
-    lastTranscript: transcriptRows,
+    lastTranscript: conversationMessages,
     lastAvailableTools: toolState.available,
     lastBlockedTools: toolState.blocked,
     lastModelMessages: modelMessages,