diff --git a/docs/plans/state.json b/docs/plans/state.json
index 7accf2a..e720e6f 100644
--- a/docs/plans/state.json
+++ b/docs/plans/state.json
@@ -5636,6 +5636,17 @@
         "docs/plans/state.json"
       ],
       "test_status": "pnpm test:run src/tools/builtin/system-info.test.ts + pnpm typecheck passing"
+    },
+    "webchat-session-header-sorting": {
+      "status": "completed",
+      "date": "2026-02-19",
+      "updated": "2026-02-19",
+      "summary": "Added session sorting controls in WebChat header with modes for Recent activity, Most messages, and Name. Session titles in the selector were upgraded to include message count and last-active timestamp for faster scanning.",
+      "files_modified": [
+        "src/gateway/ui/pages/chat.js",
+        "docs/plans/state.json"
+      ],
+      "test_status": "pnpm typecheck passing"
     }
   },
   "overall_progress": {
diff --git a/src/gateway/ui/pages/chat.js b/src/gateway/ui/pages/chat.js
index b1757e1..70d5256 100644
--- a/src/gateway/ui/pages/chat.js
+++ b/src/gateway/ui/pages/chat.js
@@ -14,6 +14,7 @@ let _searchMode = false;
 let _slashPopupIndex = -1;
 let _elements = {};
 let _pendingAttachments = [];
+let _sessionSort = 'recent';
 
 // ── Slash Command Definitions ───────────────────────────────
 
@@ -80,6 +81,62 @@ function createTimestampEl(role, timestamp) {
   return ts;
 }
 
+function formatSessionLastActive(timestamp) {
+  if (typeof timestamp !== 'number' || !Number.isFinite(timestamp)) {
+    return 'no activity';
+  }
+
+  const date = new Date(timestamp);
+  if (Number.isNaN(date.getTime())) {
+    return 'no activity';
+  }
+
+  const now = new Date();
+  const sameDay = now.getFullYear() === date.getFullYear()
+    && now.getMonth() === date.getMonth()
+    && now.getDate() === date.getDate();
+
+  if (sameDay) {
+    return `today ${new Intl.DateTimeFormat(undefined, { hour: 'numeric', minute: '2-digit' }).format(date)}`;
+  }
+
+  return new Intl.DateTimeFormat(undefined, {
+    month: 'short',
+    day: 'numeric',
+    hour: 'numeric',
+    minute: '2-digit',
+  }).format(date);
+}
+
+function sortSessions(sessions, mode) {
+  const copy = [...sessions];
+  if (mode === 'messages') {
+    copy.sort((a, b) => {
+      const byMessages = (b.messageCount ?? 0) - (a.messageCount ?? 0);
+      if (byMessages !== 0) {return byMessages;}
+      return String(a.id ?? '').localeCompare(String(b.id ?? ''));
+    });
+    return copy;
+  }
+
+  if (mode === 'name') {
+    copy.sort((a, b) => String(a.id ?? '').localeCompare(String(b.id ?? '')));
+    return copy;
+  }
+
+  // Default: most recent activity first, then message count, then name.
+  copy.sort((a, b) => {
+    const aTs = typeof a.lastMessageAt === 'number' ? a.lastMessageAt : 0;
+    const bTs = typeof b.lastMessageAt === 'number' ? b.lastMessageAt : 0;
+    const byTime = bTs - aTs;
+    if (byTime !== 0) {return byTime;}
+    const byMessages = (b.messageCount ?? 0) - (a.messageCount ?? 0);
+    if (byMessages !== 0) {return byMessages;}
+    return String(a.id ?? '').localeCompare(String(b.id ?? ''));
+  });
+  return copy;
+}
+
 function createMessageEl(role, content, timestamp = Date.now()) {
   const wrapper = document.createElement('div');
 
@@ -549,7 +606,7 @@ async function loadSessions(client) {
 
   try {
     const result = await client.call('sessions.list');
-    const sessions = result.sessions ?? [];
+    const sessions = sortSessions(result.sessions ?? [], _sessionSort);
 
     // Preserve current selection
     const current = _currentSession;
@@ -564,7 +621,9 @@ async function loadSessions(client) {
       for (const s of sessions) {
         const opt = document.createElement('option');
         opt.value = s.id;
-        opt.textContent = `${s.id} (${s.messageCount} msgs)`;
+        const msgCount = s.messageCount ?? 0;
+        const msgLabel = msgCount === 1 ? '1 msg' : `${msgCount} msgs`;
+        opt.textContent = `${s.id} · ${msgLabel} · ${formatSessionLastActive(s.lastMessageAt)}`;
         if (s.id === current) {opt.selected = true;}
         select.appendChild(opt);
       }
@@ -713,6 +772,11 @@ export const ChatPage = {
       <div class="flex flex-col h-[calc(100vh-6rem)] md:h-[calc(100vh-3rem)] max-w-3xl">
         <div class="flex items-center gap-3 pb-3 border-b border-zinc-800 mb-3 flex-wrap">
           <select id="chat-session-select" class="bg-zinc-900 text-zinc-50 border border-zinc-800 rounded-lg px-3 py-1.5 text-sm outline-none focus:border-blue-500"></select>
+          <select id="chat-session-sort" class="bg-zinc-900 text-zinc-50 border border-zinc-800 rounded-lg px-3 py-1.5 text-sm outline-none focus:border-blue-500" title="Sort sessions">
+            <option value="recent">Sort: Recent</option>
+            <option value="messages">Sort: Most messages</option>
+            <option value="name">Sort: Name</option>
+          </select>
           <button id="chat-new-session" class="px-3 py-1.5 text-sm font-medium rounded-md border border-zinc-700 bg-zinc-800 text-zinc-200 hover:bg-zinc-700 transition-colors">+ New</button>
           <button id="chat-load-history" class="px-3 py-1.5 text-sm font-medium rounded-md border border-zinc-700 bg-zinc-800 text-zinc-200 hover:bg-zinc-700 transition-colors">History</button>
         </div>
@@ -741,6 +805,7 @@ export const ChatPage = {
 
     _elements = {
       sessionSelect: el.querySelector('#chat-session-select'),
+      sessionSort: el.querySelector('#chat-session-sort'),
       messages: el.querySelector('#chat-messages'),
       input: el.querySelector('#chat-input'),
       sendBtn: el.querySelector('#chat-send'),
@@ -759,6 +824,11 @@ export const ChatPage = {
       _currentSession = _elements.sessionSelect.value || null;
     });
 
+    _elements.sessionSort.addEventListener('change', () => {
+      _sessionSort = _elements.sessionSort.value || 'recent';
+      loadSessions(client);
+    });
+
     // Event: new session
     el.querySelector('#chat-new-session').addEventListener('click', async () => {
       try {
@@ -887,6 +957,7 @@ export const ChatPage = {
     _sending = false;
     _searchMode = false;
     _slashPopupIndex = -1;
+    _sessionSort = 'recent';
     _elements = {};
     _pendingAttachments = [];
   },