diff --git a/tests/hil/tests/connection/test.c b/tests/hil/tests/connection/test.c
index 33b4c06c0..3c7ce4a0d 100644
--- a/tests/hil/tests/connection/test.c
+++ b/tests/hil/tests/connection/test.c
@@ -3,22 +3,57 @@
 
 LOG_TAG_DEFINE(test_connect);
 
+static golioth_sys_sem_t _connected_sem = NULL;
+
+static void on_client_event(struct golioth_client *client,
+                            enum golioth_client_event event,
+                            void *arg)
+{
+    bool is_connected = (event == GOLIOTH_CLIENT_EVENT_CONNECTED);
+    if (is_connected)
+    {
+        golioth_sys_sem_give(_connected_sem);
+    }
+    GLTH_LOGI(TAG, "Golioth client %s", is_connected ? "connected" : "disconnected");
+}
+
 void hil_test_entry(const struct golioth_client_config *config)
 {
+    _connected_sem = golioth_sys_sem_create(1, 0);
+
     struct golioth_client *client = golioth_client_create(config);
 
-    (void) client;
+    golioth_client_register_event_callback(client, on_client_event, NULL);
+    golioth_sys_sem_take(_connected_sem, GOLIOTH_SYS_WAIT_FOREVER);
 
-    while (1)
-    {
-        golioth_sys_msleep(10 * 1000);
+    /* Pause to ensure we don't have out-of-order logs */
+    golioth_sys_msleep(1 * 1000);
 
-        GLTH_LOGI(TAG, "Stopping client");
-        golioth_client_stop(client);
+    GLTH_LOGI(TAG, "Stopping client");
+    golioth_client_stop(client);
 
-        golioth_sys_msleep(10 * 1000);
+    golioth_sys_msleep(10 * 1000);
 
-        GLTH_LOGI(TAG, "Starting client");
-        golioth_client_start(client);
-    }
+    GLTH_LOGI(TAG, "Starting client");
+    golioth_client_start(client);
+
+    golioth_sys_sem_take(_connected_sem, GOLIOTH_SYS_WAIT_FOREVER);
+
+    /* Pause to ensure we don't have out-of-order logs */
+    golioth_sys_msleep(1 * 1000);
+
+    GLTH_LOGI(TAG, "Destroying client");
+    golioth_client_destroy(client);
+    client = NULL;
+
+    golioth_sys_msleep(10 * 1000);
+
+    GLTH_LOGI(TAG, "Starting client");
+    client = golioth_client_create(config);
+    golioth_client_start(client);
+
+    golioth_sys_sem_take(_connected_sem, GOLIOTH_SYS_WAIT_FOREVER);
+
+    /* Pause to ensure logs are show */
+    golioth_sys_msleep(1 * 1000);
 }
diff --git a/tests/hil/tests/connection/test_connection.py b/tests/hil/tests/connection/test_connection.py
index 0d692f56d..8e8781ebc 100644
--- a/tests/hil/tests/connection/test_connection.py
+++ b/tests/hil/tests/connection/test_connection.py
@@ -10,7 +10,12 @@ async def test_connect(board, device):
     # Confirm connection to Golioth
     assert None != board.wait_for_regex_in_line('Golioth CoAP client connected', timeout_s=120)
 
-    # Wait for reconnection
-    assert None != board.wait_for_regex_in_line('Stopping client', timeout_s=10)
+    # Wait for reconnection after golioth_client_stop();
+    assert None != board.wait_for_regex_in_line('Stopping client', timeout_s=15)
+    assert None != board.wait_for_regex_in_line('Starting client', timeout_s=120)
+    assert None != board.wait_for_regex_in_line('Golioth CoAP client connected', timeout_s=120)
+
+    # Wait for reconnection after golioth_client_destroy();
+    assert None != board.wait_for_regex_in_line('Destroying client', timeout_s=15)
     assert None != board.wait_for_regex_in_line('Starting client', timeout_s=120)
     assert None != board.wait_for_regex_in_line('Golioth CoAP client connected', timeout_s=120)