diff --git a/ports/esp32/modsocket.c b/ports/esp32/modsocket.c
index fe76b5f760..cacc52dec5 100644
--- a/ports/esp32/modsocket.c
+++ b/ports/esp32/modsocket.c
@@ -82,6 +82,8 @@ typedef struct _socket_obj_t {
     #endif
 } socket_obj_t;
 
+STATIC const char *TAG = "modsocket";
+
 void _socket_settimeout(socket_obj_t *sock, uint64_t timeout_ms);
 
 #if MICROPY_PY_SOCKET_EVENTS
@@ -364,16 +366,96 @@ STATIC MP_DEFINE_CONST_FUN_OBJ_1(socket_accept_obj, socket_accept);
 STATIC mp_obj_t socket_connect(const mp_obj_t arg0, const mp_obj_t arg1) {
     socket_obj_t *self = MP_OBJ_TO_PTR(arg0);
     struct addrinfo *res;
+    bool blocking = false;
+    int flags;
+    int raise_err = 0;
+
     _socket_getaddrinfo(arg1, &res);
     MP_THREAD_GIL_EXIT();
     self->state = SOCKET_STATE_CONNECTED;
-    int r = lwip_connect(self->fd, res->ai_addr, res->ai_addrlen);
-    MP_THREAD_GIL_ENTER();
-    lwip_freeaddrinfo(res);
-    if (r != 0) {
-        mp_raise_OSError(errno);
+
+    flags = fcntl(self->fd, F_GETFL);
+
+    blocking = (flags & O_NONBLOCK) == 0;
+
+    if (blocking) {
+        // For blocking sockets, make the socket temporarily non-blocking and emulate
+        // blocking using select.
+        //
+        // This has two benefits:
+        //
+        // - Allows handling external exceptions while waiting for connect.
+        //
+        // - Allows emulating a connect timeout, which is not supported by LWIP or
+        //   required by POSIX but is normal behaviour for CPython.
+        if (fcntl(self->fd, F_SETFL, flags | O_NONBLOCK) < 0) {
+            ESP_LOGE(TAG, "fcntl set failed %d", errno); // Unexpected internal failure
+            raise_err = errno;
+        }
     }
 
+    if (raise_err == 0) {
+        // Try performing the actual connect. Expected to always return immediately.
+        int r = lwip_connect(self->fd, res->ai_addr, res->ai_addrlen);
+        if (r != 0) {
+            raise_err = errno;
+        }
+    }
+
+    if (blocking) {
+        // Set the socket back to blocking. We can still pass it to select() in this state.
+        int r = fcntl(self->fd, F_SETFL, flags);
+        if (r != 0 && (raise_err == 0 || raise_err == EINPROGRESS)) {
+            ESP_LOGE(TAG, "fcntl restore failed %d", errno); // Unexpected internal failure
+            raise_err = errno;
+        }
+    }
+
+    lwip_freeaddrinfo(res);
+
+    if (blocking && raise_err == EINPROGRESS) {
+        // Keep calling select() until the socket is marked writable (i.e. connected),
+        // or an error or a timeout occurs
+
+        // Note: _socket_settimeout() always sets self->retries != 0 on blocking sockets.
+
+        for (unsigned int i = 0; i <= self->retries; i++) {
+            struct timeval timeout = {
+                .tv_sec = 0,
+                .tv_usec = SOCKET_POLL_US,
+            };
+            fd_set wfds;
+            FD_ZERO(&wfds);
+            FD_SET(self->fd, &wfds);
+
+            int r = select(self->fd + 1, NULL, &wfds, NULL, &timeout);
+            if (r < 0) {
+                // Error condition
+                raise_err = errno;
+                break;
+            } else if (r > 0) {
+                // Select indicated the socket is writable. Check for any error.
+                socklen_t socklen = sizeof(raise_err);
+                r = getsockopt(self->fd, SOL_SOCKET, SO_ERROR, &raise_err, &socklen);
+                if (r < 0) {
+                    raise_err = errno;
+                }
+                break;
+            } else {
+                // Select timed out
+                raise_err = ETIMEDOUT;
+
+                MP_THREAD_GIL_ENTER();
+                check_for_exceptions();
+                MP_THREAD_GIL_EXIT();
+            }
+        }
+    }
+
+    MP_THREAD_GIL_ENTER();
+    if (raise_err) {
+        mp_raise_OSError(raise_err);
+    }
     return mp_const_none;
 }
 STATIC MP_DEFINE_CONST_FUN_OBJ_2(socket_connect_obj, socket_connect);
@@ -847,7 +929,7 @@ STATIC MP_DEFINE_CONST_FUN_OBJ_VAR_BETWEEN(esp_socket_getaddrinfo_obj, 2, 6, esp
 STATIC mp_obj_t esp_socket_initialize() {
     static int initialized = 0;
     if (!initialized) {
-        ESP_LOGI("modsocket", "Initializing");
+        ESP_LOGI(TAG, "Initializing");
         esp_netif_init();
         initialized = 1;
     }