diff --git a/components/wifi/esp8266-driver/ESP8266Interface.cpp b/components/wifi/esp8266-driver/ESP8266Interface.cpp
index 9fc7fe10432..c1bec64ff43 100644
--- a/components/wifi/esp8266-driver/ESP8266Interface.cpp
+++ b/components/wifi/esp8266-driver/ESP8266Interface.cpp
@@ -184,13 +184,20 @@ void ESP8266Interface::_connect_async()
         return;
     }
     _connect_retval = _esp.connect(ap_ssid, ap_pass);
+    int timeleft_ms = ESP8266_INTERFACE_CONNECT_TIMEOUT_MS - _conn_timer.read_ms();
     if (_connect_retval == NSAPI_ERROR_OK || _connect_retval == NSAPI_ERROR_AUTH_FAILURE
-            || _connect_retval == NSAPI_ERROR_NO_SSID) {
+            || _connect_retval == NSAPI_ERROR_NO_SSID
+            || ((_if_blocking == true) && (timeleft_ms <= 0))) {
         _connect_event_id = 0;
+        _conn_timer.stop();
+        if (timeleft_ms <= 0) {
+            _connect_retval = NSAPI_ERROR_CONNECTION_TIMEOUT;
+        }
         _if_connected.notify_all();
     } else {
         // Postpone to give other stuff time to run
-        _connect_event_id = _global_event_queue->call_in(ESP8266_CONNECT_TIMEOUT, callback(this, &ESP8266Interface::_connect_async));
+        _connect_event_id = _global_event_queue->call_in(ESP8266_INTERFACE_CONNECT_INTERVAL_MS,
+                                                         callback(this, &ESP8266Interface::_connect_async));
         if (!_connect_event_id) {
             MBED_ERROR(MBED_MAKE_ERROR(MBED_MODULE_DRIVER, MBED_ERROR_CODE_ENOMEM), \
                        "ESP8266Interface::_connect_async(): unable to add event to queue. Increase \"events.shared-eventsize\"\n");
@@ -233,6 +240,9 @@ int ESP8266Interface::connect()
 
     _connect_retval = NSAPI_ERROR_NO_CONNECTION;
     MBED_ASSERT(!_connect_event_id);
+    _conn_timer.stop();
+    _conn_timer.reset();
+    _conn_timer.start();
     _connect_event_id = _global_event_queue->call(callback(this, &ESP8266Interface::_connect_async));
 
     if (!_connect_event_id) {
@@ -315,7 +325,7 @@ int ESP8266Interface::disconnect()
     _initialized = false;
 
     nsapi_error_t status = _conn_status_to_error();
-    if (status == NSAPI_ERROR_NO_CONNECTION || !get_ip_address()) {
+    if (status == NSAPI_ERROR_NO_CONNECTION) {
         return NSAPI_ERROR_NO_CONNECTION;
     }
 
diff --git a/components/wifi/esp8266-driver/ESP8266Interface.h b/components/wifi/esp8266-driver/ESP8266Interface.h
index 1166f6892e2..1f8dfb11c3d 100644
--- a/components/wifi/esp8266-driver/ESP8266Interface.h
+++ b/components/wifi/esp8266-driver/ESP8266Interface.h
@@ -19,6 +19,7 @@
 
 #if DEVICE_SERIAL && DEVICE_INTERRUPTIN && defined(MBED_CONF_EVENTS_PRESENT) && defined(MBED_CONF_NSAPI_PRESENT) && defined(MBED_CONF_RTOS_PRESENT)
 #include "drivers/DigitalOut.h"
+#include "drivers/Timer.h"
 #include "ESP8266/ESP8266.h"
 #include "events/EventQueue.h"
 #include "events/mbed_shared_queues.h"
@@ -34,6 +35,9 @@
 
 #define ESP8266_SOCKET_COUNT 5
 
+#define ESP8266_INTERFACE_CONNECT_INTERVAL_MS (5000)
+#define ESP8266_INTERFACE_CONNECT_TIMEOUT_MS (2 * ESP8266_CONNECT_TIMEOUT + ESP8266_INTERFACE_CONNECT_INTERVAL_MS)
+
 #ifdef TARGET_FF_ARDUINO
 #ifndef MBED_CONF_ESP8266_TX
 #define MBED_CONF_ESP8266_TX D1
@@ -94,6 +98,9 @@ class ESP8266Interface : public NetworkStack, public WiFiInterface {
      *
      *  Attempts to connect to a WiFi network.
      *
+     *  If interface is configured blocking it will timeout after up to
+     *  ESP8266_INTERFACE_CONNECT_TIMEOUT_MS + ESP8266_CONNECT_TIMEOUT ms.
+     *
      *  @param ssid      Name of the network to connect to
      *  @param pass      Security passphrase to connect to the network
      *  @param security  Type of encryption for connection (Default: NSAPI_SECURITY_NONE)
@@ -408,6 +415,7 @@ class ESP8266Interface : public NetworkStack, public WiFiInterface {
 
     // connect status reporting
     nsapi_error_t _conn_status_to_error();
+    mbed::Timer _conn_timer;
 
     // Drivers's socket info
     struct _sock_info {