diff --git a/esphome/components/socket/lwip_raw_tcp_impl.cpp b/esphome/components/socket/lwip_raw_tcp_impl.cpp
index 3d1679553e..cfd8cf0daa 100644
--- a/esphome/components/socket/lwip_raw_tcp_impl.cpp
+++ b/esphome/components/socket/lwip_raw_tcp_impl.cpp
@@ -857,16 +857,16 @@ err_t LWIPRawListenImpl::accept_fn_(struct tcp_pcb *newpcb, err_t err) {
   tcp_err(newpcb, LWIPRawListenImpl::s_queued_err_fn);
   tcp_recv(newpcb, LWIPRawListenImpl::s_queued_recv_fn);
   LWIP_LOG("Accepted connection, queue size: %d", this->accepted_socket_count_);
-  // Wake the main loop immediately so it can accept the new connection.
-  esphome::wake_loop_any_context();
 #ifdef USE_OTA
   // Mark the OTA component loop to be re-enabled if it disabled itself while idle.
-  // This only sets pending-enable flags; the wake_loop_any_context() call above has
-  // already woken the main loop, which will process the pending enable on its next
-  // iteration. Safe to call from RP2040's low-priority user IRQ context — it only
-  // writes volatile bools, no heap or locks.
+  // This MUST happen before wake_loop_any_context() below — otherwise the main loop
+  // could wake, run a full iteration, and finish before we set the pending-enable
+  // flags, losing the wake event. Safe from RP2040's low-priority user IRQ context:
+  // it only writes volatile bools, no heap or locks.
   esphome::App.wake_ota_component_any_context();
 #endif
+  // Wake the main loop immediately so it can accept the new connection.
+  esphome::wake_loop_any_context();
   return ERR_OK;
 }
 
diff --git a/esphome/core/application.cpp b/esphome/core/application.cpp
index 9b7091f59a..9311b9fbf0 100644
--- a/esphome/core/application.cpp
+++ b/esphome/core/application.cpp
@@ -450,9 +450,10 @@ void Application::enable_pending_loops_() {
 }
 
 #if defined(USE_OTA) && defined(USE_LWIP_FAST_SELECT)
-// Called from the LwIP TCP/IP task via esphome_socket_event_callback() on NETCONN_EVT_RCVPLUS.
-// Only marks the OTA component as pending loop-enable; the fast-select callback itself has
-// already woken the main task via xTaskNotifyGive().
+// Called from the LwIP TCP/IP task via esphome_socket_event_callback() on NETCONN_EVT_RCVPLUS,
+// BEFORE the callback calls xTaskNotifyGive() — the flag-set must happen before the wake,
+// otherwise the main task could wake, run a full iteration, and miss the pending-enable.
+// Only marks the OTA component as pending loop-enable; does not itself wake the main task.
 extern "C" void esphome_wake_ota_component_any_context() { App.wake_ota_component_any_context(); }
 #endif
 
diff --git a/esphome/core/lwip_fast_select.c b/esphome/core/lwip_fast_select.c
index 32b79f288d..96eddf00ff 100644
--- a/esphome/core/lwip_fast_select.c
+++ b/esphome/core/lwip_fast_select.c
@@ -180,16 +180,17 @@ static void esphome_socket_event_callback(struct netconn *conn, enum netconn_evt
   // (rcvevent++ with a NULL pbuf or error in recvmbox), so error conditions
   // already wake the main loop through the RCVPLUS path.
   if (evt == NETCONN_EVT_RCVPLUS) {
+#ifdef USE_OTA
+    // Mark the OTA component loop to be re-enabled if it disabled itself while idle.
+    // This MUST happen before xTaskNotifyGive below — otherwise the main task could
+    // wake, run a full iteration, and finish before we set the pending-enable flags,
+    // causing the wake event to be lost until the next unrelated socket activity.
+    esphome_wake_ota_component_any_context();
+#endif
     TaskHandle_t task = esphome_main_task_handle;
     if (task != NULL) {
       xTaskNotifyGive(task);
     }
-#ifdef USE_OTA
-    // Mark the OTA component loop to be re-enabled if it disabled itself while idle.
-    // Only sets pending-enable flags — the xTaskNotifyGive above has already woken
-    // the main task, which will process the pending enable on its next iteration.
-    esphome_wake_ota_component_any_context();
-#endif
   }
 }