diff --git a/web/backend/api/gateway.go b/web/backend/api/gateway.go
index ce3a9ca1e..1e2520920 100644
--- a/web/backend/api/gateway.go
+++ b/web/backend/api/gateway.go
@@ -59,6 +59,16 @@ func refreshPicoTokensLocked(configPath string) {
 	gateway.picoToken = cfg.Channels.Pico.Token.String()
 }
 
+// ensurePicoTokenCachedLocked lazily fills the in-memory pico token cache when
+// the launcher has already discovered a running gateway via pidData, but has
+// not yet refreshed the token into memory.
+func ensurePicoTokenCachedLocked(configPath string) {
+	if gateway.picoToken != "" {
+		return
+	}
+	refreshPicoTokensLocked(configPath)
+}
+
 const (
 	protocolKey = "Sec-Websocket-Protocol"
 	tokenPrefix = "token."
diff --git a/web/backend/api/pico.go b/web/backend/api/pico.go
index 0e8cd07fc..c8ef47308 100644
--- a/web/backend/api/pico.go
+++ b/web/backend/api/pico.go
@@ -56,6 +56,7 @@ func (h *Handler) createWsProxy(origProtocol string, token string) *httputil.Rev
 func (h *Handler) handleWebSocketProxy() http.HandlerFunc {
 	return func(w http.ResponseWriter, r *http.Request) {
 		gateway.mu.Lock()
+		ensurePicoTokenCachedLocked(h.configPath)
 		gatewayAvailable := gateway.pidData != nil
 		gateway.mu.Unlock()
 
diff --git a/web/backend/api/pico_test.go b/web/backend/api/pico_test.go
index beff4d77f..ee5586746 100644
--- a/web/backend/api/pico_test.go
+++ b/web/backend/api/pico_test.go
@@ -377,6 +377,55 @@ func TestHandleWebSocketProxyReloadsGatewayTargetFromConfig(t *testing.T) {
 	}
 }
 
+func TestHandleWebSocketProxyLoadsCachedPicoTokenWhenMissing(t *testing.T) {
+	configPath := filepath.Join(t.TempDir(), "config.json")
+	h := NewHandler(configPath)
+	handler := h.handleWebSocketProxy()
+
+	server := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		if r.URL.Path != "/pico/ws" {
+			t.Fatalf("path = %q, want %q", r.URL.Path, "/pico/ws")
+		}
+		w.WriteHeader(http.StatusOK)
+		_, _ = io.WriteString(w, "proxied")
+	}))
+	defer server.Close()
+
+	cfg := config.DefaultConfig()
+	cfg.Gateway.Host = "127.0.0.1"
+	cfg.Gateway.Port = mustGatewayTestPort(t, server.URL)
+	cfg.Channels.Pico.Enabled = true
+	cfg.Channels.Pico.SetToken("cached-token")
+	if err := config.SaveConfig(configPath, cfg); err != nil {
+		t.Fatalf("SaveConfig() error = %v", err)
+	}
+
+	origPidData := gateway.pidData
+	origPicoToken := gateway.picoToken
+	t.Cleanup(func() {
+		gateway.pidData = origPidData
+		gateway.picoToken = origPicoToken
+	})
+
+	gateway.pidData = &ppid.PidFileData{}
+	gateway.picoToken = ""
+
+	req := httptest.NewRequest(http.MethodGet, "/pico/ws?session_id=test-session", nil)
+	req.Header.Set(protocolKey, tokenPrefix+"cached-token")
+	rec := httptest.NewRecorder()
+	handler(rec, req)
+
+	if rec.Code != http.StatusOK {
+		t.Fatalf("status = %d, want %d", rec.Code, http.StatusOK)
+	}
+	if body := rec.Body.String(); body != "proxied" {
+		t.Fatalf("body = %q, want %q", body, "proxied")
+	}
+	if gateway.picoToken != "cached-token" {
+		t.Fatalf("gateway.picoToken = %q, want %q", gateway.picoToken, "cached-token")
+	}
+}
+
 func mustGatewayTestPort(t *testing.T, rawURL string) int {
 	t.Helper()