diff --git a/esphome/components/wifi/wifi_component.cpp b/esphome/components/wifi/wifi_component.cpp
index c4bfdf3c42..e9b78c9225 100644
--- a/esphome/components/wifi/wifi_component.cpp
+++ b/esphome/components/wifi/wifi_component.cpp
@@ -1464,6 +1464,12 @@ void WiFiComponent::check_connecting_finished(uint32_t now) {
 
     this->release_scan_results_();
 
+#ifdef USE_WIFI_CONNECT_STATE_LISTENERS
+    // Notify listeners now that state machine has reached STA_CONNECTED
+    // This ensures wifi.connected condition returns true in listener automations
+    this->notify_connect_state_listeners_();
+#endif
+
     return;
   }
 
@@ -2183,6 +2189,21 @@ void WiFiComponent::release_scan_results_() {
   }
 }
 
+#ifdef USE_WIFI_CONNECT_STATE_LISTENERS
+void WiFiComponent::notify_connect_state_listeners_() {
+  if (!this->pending_.connect_state)
+    return;
+  this->pending_.connect_state = false;
+  // Get current SSID and BSSID from the WiFi driver
+  char ssid_buf[SSID_BUFFER_SIZE];
+  const char *ssid = this->wifi_ssid_to(ssid_buf);
+  bssid_t bssid = this->wifi_bssid();
+  for (auto *listener : this->connect_state_listeners_) {
+    listener->on_wifi_connect_state(StringRef(ssid, strlen(ssid)), bssid);
+  }
+}
+#endif  // USE_WIFI_CONNECT_STATE_LISTENERS
+
 void WiFiComponent::check_roaming_(uint32_t now) {
   // Guard: not for hidden networks (may not appear in scan)
   const WiFiAP *selected = this->get_selected_sta_();
diff --git a/esphome/components/wifi/wifi_component.h b/esphome/components/wifi/wifi_component.h
index 4bdc253f66..98f339809a 100644
--- a/esphome/components/wifi/wifi_component.h
+++ b/esphome/components/wifi/wifi_component.h
@@ -632,6 +632,11 @@ class WiFiComponent : public Component {
   /// Free scan results memory unless a component needs them
   void release_scan_results_();
 
+#ifdef USE_WIFI_CONNECT_STATE_LISTENERS
+  /// Notify connect state listeners (called after state machine reaches STA_CONNECTED)
+  void notify_connect_state_listeners_();
+#endif
+
 #ifdef USE_ESP8266
   static void wifi_event_callback(System_Event_t *event);
   void wifi_scan_done_callback_(void *arg, STATUS status);
@@ -739,6 +744,16 @@ class WiFiComponent : public Component {
   SemaphoreHandle_t high_performance_semaphore_{nullptr};
 #endif
 
+#ifdef USE_WIFI_CONNECT_STATE_LISTENERS
+  // Pending listener notifications deferred until state machine reaches appropriate state.
+  // Listeners are notified after state transitions complete so conditions like
+  // wifi.connected return correct values in automations.
+  // Uses bitfields to minimize memory; more flags may be added as needed.
+  struct {
+    bool connect_state : 1;  // Notify connect state listeners after STA_CONNECTED
+  } pending_{};
+#endif
+
 #ifdef USE_WIFI_CONNECT_TRIGGER
   Trigger<> connect_trigger_;
 #endif
diff --git a/esphome/components/wifi/wifi_component_esp8266.cpp b/esphome/components/wifi/wifi_component_esp8266.cpp
index c714afaad3..c6bd40037d 100644
--- a/esphome/components/wifi/wifi_component_esp8266.cpp
+++ b/esphome/components/wifi/wifi_component_esp8266.cpp
@@ -500,6 +500,10 @@ const LogString *get_disconnect_reason_str(uint8_t reason) {
   }
 }
 
+// TODO: This callback runs in ESP8266 system context with limited stack (~2KB).
+// All listener notifications should be deferred to wifi_loop_() via pending_ flags
+// to avoid stack overflow. Currently only connect_state is deferred; disconnect,
+// IP, and scan listeners still run in this context and should be migrated.
 void WiFiComponent::wifi_event_callback(System_Event_t *event) {
   switch (event->event) {
     case EVENT_STAMODE_CONNECTED: {
@@ -512,9 +516,9 @@ void WiFiComponent::wifi_event_callback(System_Event_t *event) {
 #endif
       s_sta_connected = true;
 #ifdef USE_WIFI_CONNECT_STATE_LISTENERS
-      for (auto *listener : global_wifi_component->connect_state_listeners_) {
-        listener->on_wifi_connect_state(StringRef(it.ssid, it.ssid_len), it.bssid);
-      }
+      // Defer listener notification until state machine reaches STA_CONNECTED
+      // This ensures wifi.connected condition returns true in listener automations
+      global_wifi_component->pending_.connect_state = true;
 #endif
       // For static IP configurations, GOT_IP event may not fire, so notify IP listeners here
 #if defined(USE_WIFI_IP_STATE_LISTENERS) && defined(USE_WIFI_MANUAL_IP)
diff --git a/esphome/components/wifi/wifi_component_esp_idf.cpp b/esphome/components/wifi/wifi_component_esp_idf.cpp
index a32232a758..22bf4be483 100644
--- a/esphome/components/wifi/wifi_component_esp_idf.cpp
+++ b/esphome/components/wifi/wifi_component_esp_idf.cpp
@@ -710,6 +710,9 @@ void WiFiComponent::wifi_loop_() {
     delete data;  // NOLINT(cppcoreguidelines-owning-memory)
   }
 }
+// Events are processed from queue in main loop context, but listener notifications
+// must be deferred until after the state machine transitions (in check_connecting_finished)
+// so that conditions like wifi.connected return correct values in automations.
 void WiFiComponent::wifi_process_event_(IDFWiFiEvent *data) {
   esp_err_t err;
   if (data->event_base == WIFI_EVENT && data->event_id == WIFI_EVENT_STA_START) {
@@ -743,9 +746,9 @@ void WiFiComponent::wifi_process_event_(IDFWiFiEvent *data) {
 #endif
     s_sta_connected = true;
 #ifdef USE_WIFI_CONNECT_STATE_LISTENERS
-    for (auto *listener : this->connect_state_listeners_) {
-      listener->on_wifi_connect_state(StringRef(it.ssid, it.ssid_len), it.bssid);
-    }
+    // Defer listener notification until state machine reaches STA_CONNECTED
+    // This ensures wifi.connected condition returns true in listener automations
+    this->pending_.connect_state = true;
 #endif
     // For static IP configurations, GOT_IP event may not fire, so notify IP listeners here
 #if defined(USE_WIFI_IP_STATE_LISTENERS) && defined(USE_WIFI_MANUAL_IP)
diff --git a/esphome/components/wifi/wifi_component_libretiny.cpp b/esphome/components/wifi/wifi_component_libretiny.cpp
index af2b82c3c6..285a520ef5 100644
--- a/esphome/components/wifi/wifi_component_libretiny.cpp
+++ b/esphome/components/wifi/wifi_component_libretiny.cpp
@@ -423,7 +423,10 @@ void WiFiComponent::wifi_event_callback_(esphome_wifi_event_id_t event, esphome_
   }
 }
 
-// Process a single event from the queue - runs in main loop context
+// Process a single event from the queue - runs in main loop context.
+// Listener notifications must be deferred until after the state machine transitions
+// (in check_connecting_finished) so that conditions like wifi.connected return
+// correct values in automations.
 void WiFiComponent::wifi_process_event_(LTWiFiEvent *event) {
   switch (event->event_id) {
     case ESPHOME_EVENT_ID_WIFI_READY: {
@@ -456,9 +459,9 @@ void WiFiComponent::wifi_process_event_(LTWiFiEvent *event) {
       // This matches ESP32 IDF behavior where s_sta_connected is set but
       // wifi_sta_connect_status_() also checks got_ipv4_address_
 #ifdef USE_WIFI_CONNECT_STATE_LISTENERS
-      for (auto *listener : this->connect_state_listeners_) {
-        listener->on_wifi_connect_state(StringRef(it.ssid, it.ssid_len), it.bssid);
-      }
+      // Defer listener notification until state machine reaches STA_CONNECTED
+      // This ensures wifi.connected condition returns true in listener automations
+      this->pending_.connect_state = true;
 #endif
       // For static IP configurations, GOT_IP event may not fire, so set connected state here
 #ifdef USE_WIFI_MANUAL_IP
diff --git a/esphome/components/wifi/wifi_component_pico_w.cpp b/esphome/components/wifi/wifi_component_pico_w.cpp
index 84c10d5d43..1ce36c2d93 100644
--- a/esphome/components/wifi/wifi_component_pico_w.cpp
+++ b/esphome/components/wifi/wifi_component_pico_w.cpp
@@ -252,6 +252,10 @@ network::IPAddress WiFiComponent::wifi_dns_ip_(int num) {
   return network::IPAddress(dns_ip);
 }
 
+// Pico W uses polling for connection state detection.
+// Connect state listener notifications are deferred until after the state machine
+// transitions (in check_connecting_finished) so that conditions like wifi.connected
+// return correct values in automations.
 void WiFiComponent::wifi_loop_() {
   // Handle scan completion
   if (this->state_ == WIFI_COMPONENT_STATE_STA_SCANNING && !cyw43_wifi_scan_active(&cyw43_state)) {
@@ -278,11 +282,9 @@ void WiFiComponent::wifi_loop_() {
     s_sta_was_connected = true;
     ESP_LOGV(TAG, "Connected");
 #ifdef USE_WIFI_CONNECT_STATE_LISTENERS
-    String ssid = WiFi.SSID();
-    bssid_t bssid = this->wifi_bssid();
-    for (auto *listener : this->connect_state_listeners_) {
-      listener->on_wifi_connect_state(StringRef(ssid.c_str(), ssid.length()), bssid);
-    }
+    // Defer listener notification until state machine reaches STA_CONNECTED
+    // This ensures wifi.connected condition returns true in listener automations
+    this->pending_.connect_state = true;
 #endif
     // For static IP configurations, notify IP listeners immediately as the IP is already configured
 #if defined(USE_WIFI_IP_STATE_LISTENERS) && defined(USE_WIFI_MANUAL_IP)