diff --git a/src/tcp_proxy.c b/src/tcp_proxy.c
index 84d96257..ff81c3a2 100644
--- a/src/tcp_proxy.c
+++ b/src/tcp_proxy.c
@@ -93,13 +93,21 @@ static int send_data(struct proxy_conn* pc, const uint8_t* data, uint16_t len) {
 }
 
 static int send_close(struct proxy_conn* pc) {
-    return proxy_send_msg(pc->proxy->inst, pc->proxy->via_node_id,
-                           TCP_PROXY_SUBCMD_CLOSE, pc->stream_id, NULL, 0);
+    int ret = proxy_send_msg(pc->proxy->inst, pc->proxy->via_node_id,
+                              TCP_PROXY_SUBCMD_CLOSE, pc->stream_id, NULL, 0);
+    if (ret < 0) { pc->close_pending = 1; return -1; }
+    pc->close_pending = 0;
+    pc->close_sent = 1;
+    return 0;
 }
 
 static int send_error(struct proxy_conn* pc) {
-    return proxy_send_msg(pc->proxy->inst, pc->proxy->via_node_id,
-                           TCP_PROXY_SUBCMD_ERROR, pc->stream_id, NULL, 0);
+    int ret = proxy_send_msg(pc->proxy->inst, pc->proxy->via_node_id,
+                              TCP_PROXY_SUBCMD_ERROR, pc->stream_id, NULL, 0);
+    if (ret < 0) { pc->close_pending = 1; return -1; }
+    pc->close_pending = 0;
+    pc->close_sent = 1;
+    return 0;
 }
 
 // ====================================================================
@@ -238,9 +246,8 @@ static err_t proxy_recv_cb(void *arg, struct tcp_pcb *pcb, struct pbuf *p, err_t
         { uint16_t wnd_gap = TCP_WND_MAX(pcb) - pcb->rcv_wnd;
           if (wnd_gap > 0) tcp_recved(pcb, wnd_gap); }
         pc->tun_closed = 1;
-        if (!pc->close_sent) {
+        if (!pc->close_sent && !pc->close_pending) {
             if (send_close(pc) < 0) DEBUG_ERROR(DEBUG_CATEGORY_SOCKET, "PROXY FIN send_close failed sid=%08x", pc->stream_id);
-            pc->close_sent = 1;
         }
         return LERR_OK;
     }
@@ -276,7 +283,6 @@ static void proxy_err_cb(void *arg, err_t err) {
                  err, pc->stream_id, pc->pcb ? pc->pcb->state : 0, pc->tun_closed, pc->rem_closed, pc->connected);
     pc->error = 1;
     if (send_error(pc) < 0) DEBUG_ERROR(DEBUG_CATEGORY_SOCKET, "PROXY send_error failed sid=%08x", pc->stream_id);
-    pc->close_sent = 1;
 }
 
 static err_t proxy_poll_cb(void *arg, struct tcp_pcb *pcb) {
@@ -290,6 +296,12 @@ static err_t proxy_poll_cb(void *arg, struct tcp_pcb *pcb) {
         return LERR_OK;
     }
 
+    /* Retry pending CLOSE/ERROR if previous send failed */
+    if (pc->close_pending) {
+        if (pc->error) send_error(pc);
+        else send_close(pc);
+    }
+
     if (pc->tun_closed && pc->rem_closed && pc->pcb) {
         uint32_t pending = pc->to_lwip ? queue_entry_count(pc->to_lwip) : 0;
         int done = (pending == 0 && pcb->unsent == NULL && pcb->unacked == NULL);
diff --git a/src/tcp_proxy.h b/src/tcp_proxy.h
index 00b6bd8b..f6369fa4 100644
--- a/src/tcp_proxy.h
+++ b/src/tcp_proxy.h
@@ -32,6 +32,7 @@ struct proxy_conn {
     uint8_t  rem_closed;       // exit отправил CLOSE
     uint8_t  error;            // ошибка, немедленная очистка
     uint8_t  close_sent;       // отправили CLOSE/ERROR в exit
+    uint8_t  close_pending;    // CLOSE/ERROR не доставлен, ждём повтора
     uint8_t  connected;        // CONNECTED(OK) получен от exit
 
     uint8_t  dest_ip[4];