diff --git a/api/endpoints/chat.php b/api/endpoints/chat.php
index 4d85852..99bb674 100644
--- a/api/endpoints/chat.php
+++ b/api/endpoints/chat.php
@@ -72,13 +72,27 @@ JarvisDB::insert(
     [$sessionId, 'user', $message]
 );
 
-// Conversation history
+// Conversation history — current session
 $history = JarvisDB::query(
     'SELECT role, content FROM conversations WHERE session_id=? ORDER BY created_at DESC LIMIT 10',
     [$sessionId]
-);
+) ?? [];
 $history = array_reverse($history);
 
+// Cross-session memory: last 6 turns from the most recent prior session
+$priorSession = JarvisDB::query(
+    "SELECT session_id FROM conversations WHERE session_id != ? AND role='user'
+     ORDER BY created_at DESC LIMIT 1",
+    [$sessionId]
+);
+if ($priorSession && !empty($priorSession[0]['session_id'])) {
+    $priorHistory = JarvisDB::query(
+        'SELECT role, content FROM conversations WHERE session_id=? ORDER BY created_at DESC LIMIT 6',
+        [$priorSession[0]['session_id']]
+    ) ?? [];
+    $history = array_merge(array_reverse($priorHistory), $history);
+}
+
 $reply  = null;
 $source = 'unknown';
 
@@ -1633,6 +1647,44 @@ if (!$reply) {
     if ($matched && $matched['action'] === 'action') {
         switch ($matched['intent']) {
 
+            case 'restart_agent':
+                // Extract target hostname from message
+                $msgLow = strtolower($message);
+                $agentMap = [
+                    'homebridge'    => 'homebridge_b57cbaea',
+                    'jellyfin'      => 'jellyfin_7e386833',
+                    'networkbackup' => 'networkbackup_NetworkB',
+                    'network backup'=> 'networkbackup_NetworkB',
+                    'novacpx'       => 'novacpx_e3b07264',
+                    'nova'          => 'novacpx_e3b07264',
+                    'mediastack'    => 'MediaStack_2c00b1b8',
+                    'media stack'   => 'MediaStack_2c00b1b8',
+                    'homeassistant' => 'homeassistant_ha',
+                    'home assistant'=> 'homeassistant_ha',
+                ];
+                $targetAgentId = null;
+                $targetName    = null;
+                foreach ($agentMap as $keyword => $agentId) {
+                    if (str_contains($msgLow, $keyword)) {
+                        $targetAgentId = $agentId;
+                        $targetName    = ucfirst($keyword);
+                        break;
+                    }
+                }
+                if ($targetAgentId) {
+                    JarvisDB::insert(
+                        "INSERT INTO agent_commands (agent_id, command_type, command_data, status, created_at)
+                         VALUES (?, 'restart_service', ?, 'pending', NOW())",
+                        [$targetAgentId, json_encode(['service' => 'jarvis-agent'])]
+                    );
+                    $reply  = "Restart command sent to the {$targetName} agent, {$userAddr}. It should come back online within 15 seconds.";
+                } else {
+                    // Fall back to listing restartable agents
+                    $reply = "Which agent should I restart, {$userAddr}? I can restart: HomeAssistant, Homebridge, Jellyfin, MediaStack, NetworkBackup, or NovaCPX.";
+                }
+                $source = 'intent:restart_agent';
+                break;
+
             case 'focus_mode':
                 $uiAction = 'focus_mode';
                 $reply = "Focus mode activated, {$userAddr}. Side panels hidden.";
diff --git a/public_html/index.html b/public_html/index.html
index 9e627b8..e2c94f3 100644
--- a/public_html/index.html
+++ b/public_html/index.html
@@ -2584,6 +2584,8 @@ function showApp(name, greeting, silent = false) {
   loadWeather();
   loadNews();
   initMobile();
+  setTimeout(checkPlannerReminder, 3000);
+  setInterval(checkUpcomingAppts, 300000);
   // Guardian Mode — badge refresh + proactive chat
   setTimeout(() => {
     _refreshGuardianBadge();
@@ -3157,6 +3159,52 @@ async function toggleHA(entityId, domain, currentState) {
   } catch(e) {}
 }
 
+// ── PROACTIVE REMINDERS ──────────────────────────────────────────────────────
+let _reminderShown = false;
+async function checkPlannerReminder() {
+  if (_reminderShown || sessionStorage.getItem('reminderShown')) return;
+  _reminderShown = true;
+  sessionStorage.setItem('reminderShown', '1');
+  const d = await api('planner/today').catch(() => null);
+  if (!d) return;
+  const tasks    = [...(d.tasks_overdue||[]), ...(d.tasks_today||[])];
+  const appts    = d.appts_today || [];
+  const overdue  = d.tasks_overdue?.length || 0;
+  if (!tasks.length && !appts.length) return;
+
+  const parts = [];
+  if (overdue)       parts.push(overdue + ' overdue task' + (overdue > 1 ? 's' : ''));
+  if (tasks.length - overdue > 0) parts.push((tasks.length - overdue) + ' task' + (tasks.length - overdue > 1 ? 's' : '') + ' due today');
+  if (appts.length)  {
+    const nextAppt = appts[0];
+    const t = nextAppt.start_at ? new Date(nextAppt.start_at).toLocaleTimeString('en-US',{hour:'2-digit',minute:'2-digit',hour12:true}) : '';
+    parts.push((t ? 'appointment at ' + t : appts.length + ' appointment' + (appts.length > 1 ? 's' : '') + ' today'));
+  }
+
+  const msg = 'Heads up, ' + (sessionUser||'Sir') + '. You have ' + parts.join(' and ') + '.';
+  addMessage('jarvis', msg);
+  if (typeof speak === 'function' && isVoiceActive) speak(msg);
+}
+
+// Check for upcoming appointments (fires every 5 min after load)
+let _apptAlerted = new Set();
+async function checkUpcomingAppts() {
+  const d = await api('planner/today').catch(() => null);
+  if (!d) return;
+  const now = Date.now();
+  for (const a of (d.appts_today||[])) {
+    if (!a.start_at || _apptAlerted.has(a.id)) continue;
+    const start = new Date(a.start_at).getTime();
+    const minsUntil = (start - now) / 60000;
+    if (minsUntil > 0 && minsUntil <= 15) {
+      _apptAlerted.add(a.id);
+      const msg = 'Reminder: ' + a.title + ' starts in ' + Math.round(minsUntil) + ' minutes' + (a.location ? ' at ' + a.location : '') + '.';
+      addMessage('jarvis', msg);
+      if (typeof speak === 'function' && isVoiceActive) speak(msg);
+    }
+  }
+}
+
 // ── PLANNER SUMMARY (top bar badge only) ─────────────────────────────────
 async function loadPlannerSummary() {
   const d = await api('planner/today');