diff --git a/api/routes.py b/api/routes.py
index ab1173d..a27ae89 100644
--- a/api/routes.py
+++ b/api/routes.py
@@ -193,7 +193,7 @@ from api.onboarding import (
 # Approval system (optional -- graceful fallback if agent not available)
 try:
     from tools.approval import (
-        submit_pending,
+        submit_pending as _submit_pending_raw,
         approve_session,
         approve_permanent,
         save_permanent_allowlist,
@@ -204,7 +204,7 @@ try:
         resolve_gateway_approval,
     )
 except ImportError:
-    submit_pending = lambda *a, **k: None
+    _submit_pending_raw = lambda *a, **k: None
     approve_session = lambda *a, **k: None
     approve_permanent = lambda *a, **k: None
     save_permanent_allowlist = lambda *a, **k: None
@@ -214,6 +214,31 @@ except ImportError:
     _lock = threading.Lock()
     _permanent_approved = set()
 
+
+def submit_pending(session_key: str, approval: dict) -> None:
+    """Append a pending approval to the per-session queue.
+
+    Wraps the agent's submit_pending to:
+    - Add a stable approval_id (uuid4 hex) so the respond endpoint can target
+      a specific entry even when multiple approvals are queued simultaneously.
+    - Change the storage from a single overwriting dict value to a list, so
+      parallel tool calls each get their own approval slot (fixes #527).
+    """
+    entry = dict(approval)
+    entry.setdefault("approval_id", uuid.uuid4().hex)
+    with _lock:
+        queue = _pending.setdefault(session_key, [])
+        # Replace a legacy non-list value if the agent version uses the old pattern.
+        if not isinstance(queue, list):
+            _pending[session_key] = [queue]
+            queue = _pending[session_key]
+        queue.append(entry)
+    # NOTE: We do NOT call _submit_pending_raw here — that function overwrites
+    # _pending[session_key] with a single dict, which would undo the list we just
+    # built. The gateway blocking path uses _gateway_queues (a separate mechanism
+    # managed by check_all_command_guards / register_gateway_notify), which is
+    # unaffected by _pending. The _pending dict is only used for UI polling.
+
 # Clarify prompts (optional -- graceful fallback if agent not available)
 try:
     from api.clarify import (
@@ -1671,10 +1696,20 @@ def _handle_file_read(handler, parsed):
 def _handle_approval_pending(handler, parsed):
     sid = parse_qs(parsed.query).get("session_id", [""])[0]
     with _lock:
-        p = _pending.get(sid)
+        queue = _pending.get(sid)
+        # Support both the new list format and a legacy single-dict value.
+        if isinstance(queue, list):
+            p = queue[0] if queue else None
+            total = len(queue)
+        elif queue:
+            p = queue
+            total = 1
+        else:
+            p = None
+            total = 0
     if p:
-        return j(handler, {"pending": dict(p)})
-    return j(handler, {"pending": None})
+        return j(handler, {"pending": dict(p), "pending_count": total})
+    return j(handler, {"pending": None, "pending_count": 0})
 
 
 def _handle_approval_inject(handler, parsed):
@@ -2354,9 +2389,31 @@ def _handle_approval_respond(handler, body):
     choice = body.get("choice", "deny")
     if choice not in ("once", "session", "always", "deny"):
         return bad(handler, f"Invalid choice: {choice}")
-    # Pop the legacy polling-mode pending entry (no-op when gateway path is active).
+    approval_id = body.get("approval_id", "")
+
+    # Pop the targeted entry from the pending queue by approval_id.
+    # Falls back to popping the first entry for backward-compat with old clients.
+    pending = None
     with _lock:
-        pending = _pending.pop(sid, None)
+        queue = _pending.get(sid)
+        if isinstance(queue, list):
+            if approval_id:
+                # Find and remove the specific entry by approval_id.
+                for i, entry in enumerate(queue):
+                    if entry.get("approval_id") == approval_id:
+                        pending = queue.pop(i)
+                        break
+                else:
+                    # approval_id not found -- fall back to oldest entry.
+                    pending = queue.pop(0) if queue else None
+            else:
+                pending = queue.pop(0) if queue else None
+            if not queue:
+                _pending.pop(sid, None)
+        elif queue:
+            # Legacy single-dict value.
+            pending = _pending.pop(sid, None)
+
     if pending:
         keys = pending.get("pattern_keys") or [pending.get("pattern_key", "")]
         if choice in ("once", "session"):
diff --git a/static/index.html b/static/index.html
index 347b366..8a2c756 100644
--- a/static/index.html
+++ b/static/index.html
@@ -225,6 +225,7 @@
         </div>
         <div class="approval-desc" id="approvalDesc"></div>
         <div class="approval-cmd" id="approvalCmd"></div>
+        <div class="approval-counter" id="approvalCounter" style="display:none;font-size:0.75em;opacity:0.6;margin-top:4px;"></div>
         <div class="approval-btns">
           <button class="approval-btn once" id="approvalBtnOnce" onclick="respondApproval('once')" title="Allow this one command (Enter)" data-i18n-title="approval_btn_once_title">
             <span class="approval-btn-icon"><svg width="14" height="14" viewBox="0 0 24 24" fill="none" stroke="currentColor" stroke-width="2.5" stroke-linecap="round" stroke-linejoin="round" aria-hidden="true"><polyline points="20 6 9 17 4 12"/></svg></span>
diff --git a/static/messages.js b/static/messages.js
index 20e7564..8e37699 100644
--- a/static/messages.js
+++ b/static/messages.js
@@ -360,7 +360,7 @@ function attachLiveStream(activeSid, streamId, uploaded=[], options={}){
     source.addEventListener('approval',e=>{
       const d=JSON.parse(e.data);
       d._session_id=activeSid;
-      showApprovalCard(d);
+      showApprovalCard(d, 1);
       playNotificationSound();
       sendBrowserNotification('Approval required',d.description||'Tool approval needed');
     });
@@ -595,8 +595,9 @@ function hideApprovalCard(force=false) {
 
 // Track session_id of the active approval so respond goes to the right session
 let _approvalSessionId = null;
+let _approvalCurrentId = null;  // approval_id of the card currently shown
 
-function showApprovalCard(pending) {
+function showApprovalCard(pending, pendingCount) {
   const keys = pending.pattern_keys || (pending.pattern_key ? [pending.pattern_key] : []);
   const desc = (pending.description || "") + (keys.length ? " [" + keys.join(", ") + "]" : "");
   const cmd = pending.command || "";
@@ -606,7 +607,18 @@ function showApprovalCard(pending) {
   $("approvalDesc").textContent = desc;
   $("approvalCmd").textContent = cmd;
   _approvalSessionId = pending._session_id || (S.session && S.session.session_id) || null;
+  _approvalCurrentId = pending.approval_id || null;
   _approvalSignature = sig;
+  // Show "1 of N" counter when multiple approvals are queued
+  const counter = $("approvalCounter");
+  if (counter) {
+    if (pendingCount && pendingCount > 1) {
+      counter.textContent = "1 of " + pendingCount + " pending";
+      counter.style.display = "";
+    } else {
+      counter.style.display = "none";
+    }
+  }
   if (!sameApproval) {
     _approvalVisibleSince = Date.now();
     _clearApprovalHideTimer();
@@ -627,17 +639,19 @@ function showApprovalCard(pending) {
 async function respondApproval(choice) {
   const sid = _approvalSessionId || (S.session && S.session.session_id);
   if (!sid) return;
+  const approvalId = _approvalCurrentId;
   // Disable all buttons immediately to prevent double-submit
   ["approvalBtnOnce","approvalBtnSession","approvalBtnAlways","approvalBtnDeny"].forEach(id => {
     const b = $(id);
     if (b) { b.disabled = true; if (b.id === "approvalBtn" + choice.charAt(0).toUpperCase() + choice.slice(1)) b.classList.add("loading"); }
   });
   _approvalSessionId = null;
+  _approvalCurrentId = null;
   hideApprovalCard(true);
   try {
     await api("/api/approval/respond", {
       method: "POST",
-      body: JSON.stringify({ session_id: sid, choice })
+      body: JSON.stringify({ session_id: sid, choice, approval_id: approvalId })
     });
   } catch(e) { setStatus(t("approval_responding") + " " + e.message); }
 }
@@ -650,7 +664,7 @@ function startApprovalPolling(sid) {
     }
     try {
       const data = await api("/api/approval/pending?session_id=" + encodeURIComponent(sid));
-      if (data.pending) { data.pending._session_id=sid; showApprovalCard(data.pending); }
+      if (data.pending) { data.pending._session_id=sid; showApprovalCard(data.pending, data.pending_count||1); }
       else { hideApprovalCard(); }
     } catch(e) { /* ignore poll errors */ }
   }, 1500);
diff --git a/tests/test_approval_queue.py b/tests/test_approval_queue.py
new file mode 100644
index 0000000..fbcac01
--- /dev/null
+++ b/tests/test_approval_queue.py
@@ -0,0 +1,188 @@
+"""Tests for approval queue multi-entry support (issue #527).
+
+Previously _pending[sid] held one entry, so simultaneous approvals overwrote
+each other. This PR changes submit_pending() to append to a list and adds
+approval_id so /api/approval/respond can target a specific entry.
+"""
+import json
+import pathlib
+import re
+import sys
+
+REPO_ROOT = pathlib.Path(__file__).parent.parent.resolve()
+sys.path.insert(0, str(REPO_ROOT))
+
+ROUTES_SRC = (REPO_ROOT / "api" / "routes.py").read_text(encoding="utf-8")
+MESSAGES_JS = (REPO_ROOT / "static" / "messages.js").read_text(encoding="utf-8")
+INDEX_HTML = (REPO_ROOT / "static" / "index.html").read_text(encoding="utf-8")
+
+
+# ---------------------------------------------------------------------------
+# Static-analysis: Python routes
+# ---------------------------------------------------------------------------
+
+def test_submit_pending_appends_to_list():
+    """submit_pending() must append to a list, not overwrite."""
+    # The new wrapper must contain queue.append
+    assert "queue.append(entry)" in ROUTES_SRC, \
+        "submit_pending() must append entry to a list queue, not overwrite _pending[sid]"
+
+
+def test_submit_pending_adds_approval_id():
+    """Each queued entry must get a unique approval_id."""
+    assert "approval_id" in ROUTES_SRC and "uuid.uuid4().hex" in ROUTES_SRC, \
+        "submit_pending() must assign a uuid4 approval_id to each queued entry"
+
+
+def test_handle_approval_pending_returns_count():
+    """_handle_approval_pending must return pending_count in its response."""
+    assert '"pending_count"' in ROUTES_SRC, \
+        "_handle_approval_pending must include pending_count in the JSON response"
+
+
+def test_handle_approval_respond_pops_by_approval_id():
+    """_handle_approval_respond must target entry by approval_id."""
+    assert 'approval_id = body.get("approval_id"' in ROUTES_SRC, \
+        "_handle_approval_respond must read approval_id from request body"
+    assert 'entry.get("approval_id") == approval_id' in ROUTES_SRC, \
+        "_handle_approval_respond must find and pop the matching entry by approval_id"
+
+
+def test_handle_approval_respond_fallback_to_oldest():
+    """When no approval_id is given, fall back to popping the oldest entry (FIFO)."""
+    # The fallback path: queue.pop(0) when approval_id is empty
+    assert "queue.pop(0)" in ROUTES_SRC, \
+        "_handle_approval_respond must fall back to popping the oldest entry when approval_id is absent"
+
+
+def test_backward_compat_legacy_dict_value():
+    """The respond handler must tolerate a legacy single-dict value in _pending."""
+    assert "Legacy single-dict value" in ROUTES_SRC or \
+           "# Legacy single-dict" in ROUTES_SRC or \
+           "elif queue:" in ROUTES_SRC, \
+        "respond handler must handle legacy single-dict _pending values for backward compatibility"
+
+
+# ---------------------------------------------------------------------------
+# Static-analysis: JavaScript frontend
+# ---------------------------------------------------------------------------
+
+def test_respond_sends_approval_id():
+    """respondApproval() must include approval_id in the POST body."""
+    assert "approval_id: approvalId" in MESSAGES_JS, \
+        "respondApproval() must send approval_id in the POST body to /api/approval/respond"
+
+
+def test_show_approval_card_accepts_count():
+    """showApprovalCard must accept a pendingCount parameter."""
+    assert re.search(r"function showApprovalCard\(pending,\s*pendingCount\)", MESSAGES_JS), \
+        "showApprovalCard() must accept a pendingCount argument"
+
+
+def test_show_approval_card_renders_counter():
+    """showApprovalCard must display a '1 of N pending' counter when N > 1."""
+    assert '"1 of " + pendingCount + " pending"' in MESSAGES_JS or \
+           "'1 of ' + pendingCount + ' pending'" in MESSAGES_JS, \
+        "showApprovalCard() must render '1 of N pending' counter for multiple queued approvals"
+
+
+def test_approval_current_id_tracked():
+    """_approvalCurrentId must be set and cleared around each approval."""
+    assert "_approvalCurrentId" in MESSAGES_JS, \
+        "_approvalCurrentId must track the approval_id of the currently displayed card"
+    assert "_approvalCurrentId = pending.approval_id" in MESSAGES_JS or \
+           "_approvalCurrentId = pending.approval_id || null" in MESSAGES_JS, \
+        "_approvalCurrentId must be assigned from pending.approval_id"
+    # Must be nulled on respond
+    assert "_approvalCurrentId = null" in MESSAGES_JS, \
+        "_approvalCurrentId must be cleared when respondApproval() is called"
+
+
+def test_polling_passes_count_to_show():
+    """The poll loop must pass pending_count to showApprovalCard."""
+    assert "showApprovalCard(data.pending, data.pending_count" in MESSAGES_JS, \
+        "Poll loop must pass data.pending_count to showApprovalCard"
+
+
+# ---------------------------------------------------------------------------
+# HTML: counter element present
+# ---------------------------------------------------------------------------
+
+def test_approval_counter_element_exists():
+    """index.html must contain an approvalCounter element."""
+    assert 'id="approvalCounter"' in INDEX_HTML, \
+        "index.html must contain an element with id='approvalCounter' for the '1 of N' display"
+
+
+# ---------------------------------------------------------------------------
+# Functional: multiple entries behave correctly (via routes module directly)
+# ---------------------------------------------------------------------------
+
+def test_multiple_approvals_both_surfaced():
+    """Two submit_pending calls must produce two queued entries, not one."""
+    import threading
+    from api import routes as r
+
+    # Reset state
+    sid = "test-multi-approval-sid"
+    with r._lock:
+        r._pending.pop(sid, None)
+
+    r.submit_pending(sid, {"command": "cmd1", "pattern_key": "p1", "pattern_keys": ["p1"], "description": "d1"})
+    r.submit_pending(sid, {"command": "cmd2", "pattern_key": "p2", "pattern_keys": ["p2"], "description": "d2"})
+
+    with r._lock:
+        queue = r._pending.get(sid)
+
+    assert isinstance(queue, list), "After two submit_pending calls, _pending[sid] must be a list"
+    assert len(queue) == 2, f"Expected 2 queued entries, got {len(queue)}"
+    assert queue[0]["command"] == "cmd1"
+    assert queue[1]["command"] == "cmd2"
+    assert queue[0].get("approval_id"), "First entry must have an approval_id"
+    assert queue[1].get("approval_id"), "Second entry must have an approval_id"
+    assert queue[0]["approval_id"] != queue[1]["approval_id"], "Each entry must have a unique approval_id"
+
+    # Cleanup
+    with r._lock:
+        r._pending.pop(sid, None)
+
+
+def test_respond_by_approval_id_pops_correct_entry():
+    """Responding with approval_id must remove only the targeted entry."""
+    from api import routes as r
+
+    sid = "test-respond-by-id-sid"
+    with r._lock:
+        r._pending.pop(sid, None)
+
+    r.submit_pending(sid, {"command": "cmd1", "pattern_key": "p1", "pattern_keys": ["p1"], "description": "d1"})
+    r.submit_pending(sid, {"command": "cmd2", "pattern_key": "p2", "pattern_keys": ["p2"], "description": "d2"})
+
+    with r._lock:
+        queue = r._pending.get(sid, [])
+        aid2 = queue[1]["approval_id"] if len(queue) > 1 else None
+
+    assert aid2, "Second entry must have an approval_id"
+
+    # Respond to the SECOND entry by its approval_id
+    # We call the handler internals directly (no HTTP)
+    with r._lock:
+        queue = r._pending.get(sid, [])
+        popped = None
+        for i, entry in enumerate(queue):
+            if entry.get("approval_id") == aid2:
+                popped = queue.pop(i)
+                break
+
+    assert popped is not None, "Should have found and popped entry by approval_id"
+    assert popped["command"] == "cmd2", "Popped the wrong entry"
+
+    with r._lock:
+        remaining = r._pending.get(sid, [])
+
+    assert len(remaining) == 1, "One entry should remain after popping the second"
+    assert remaining[0]["command"] == "cmd1", "The remaining entry should be cmd1"
+
+    # Cleanup
+    with r._lock:
+        r._pending.pop(sid, None)