diff --git a/include/fluent-bit/flb_config.h b/include/fluent-bit/flb_config.h
index e1360e8fdef..f7cc224dac5 100644
--- a/include/fluent-bit/flb_config.h
+++ b/include/fluent-bit/flb_config.h
@@ -45,6 +45,7 @@ struct flb_config {
 
     int support_mode;         /* enterprise support mode ?      */
     int is_ingestion_active;  /* date ingestion active/allowed  */
+    int is_shutting_down;     /* is the service shutting down ? */
     int is_running;           /* service running ?              */
     double flush;             /* Flush timeout                  */
     int grace;                /* Maximum grace time on shutdown */
diff --git a/include/fluent-bit/flb_upstream.h b/include/fluent-bit/flb_upstream.h
index b7f67802aad..0393c35f6fd 100644
--- a/include/fluent-bit/flb_upstream.h
+++ b/include/fluent-bit/flb_upstream.h
@@ -82,9 +82,16 @@ struct flb_upstream {
     struct flb_tls *tls;
 #endif
 
+    struct flb_config *config;
     struct mk_list _head;
 };
 
+
+static inline int flb_upstream_is_shutting_down(struct flb_upstream *u)
+{
+    return u->config->is_shutting_down;
+}
+
 void flb_upstream_queue_init(struct flb_upstream_queue *uq);
 struct flb_upstream_queue *flb_upstream_queue_get(struct flb_upstream *u);
 void flb_upstream_list_set(struct mk_list *list);
diff --git a/src/flb_engine.c b/src/flb_engine.c
index 99f5920df5e..4ae9663a390 100644
--- a/src/flb_engine.c
+++ b/src/flb_engine.c
@@ -234,7 +234,7 @@ static inline int handle_output_event(flb_pipefd_t fd, uint64_t ts,
         flb_task_retry_clean(task, ins);
         flb_task_users_dec(task, FLB_TRUE);
     }
-    else if (ret == FLB_RETRY) {
+    else if (ret == FLB_RETRY && config->is_running && !config->is_shutting_down) {
         if (ins->retry_limit == FLB_OUT_RETRY_NONE) {
             /* cmetrics: output_dropped_records_total */
             cmt_counter_add(ins->cmt_dropped_records, ts, task->records,
@@ -859,6 +859,7 @@ int flb_engine_exit(struct flb_config *config)
     uint64_t val = FLB_ENGINE_EV_STOP;
 
     config->is_ingestion_active = FLB_FALSE;
+    config->is_shutting_down = FLB_TRUE;
 
     flb_input_pause_all(config);
 
diff --git a/src/flb_network.c b/src/flb_network.c
index d25ab457470..8036a113145 100644
--- a/src/flb_network.c
+++ b/src/flb_network.c
@@ -444,6 +444,16 @@ static int net_connect_async(int fd,
     /* Save the mask before the event handler do a reset */
     mask = u_conn->event.mask;
 
+    /*
+     * If the socket has been invalidated (e.g: timeout or shutdown), just
+     * print a debug message and return.
+     */
+    if (u_conn->fd == -1) {
+        flb_debug("[net] TCP connection not longer available: %s:%i",
+                  u->tcp_host, u->tcp_port);
+        return -1;
+    }
+
     /* We got a notification, remove the event registered */
     ret = mk_event_del(u_conn->evl, &u_conn->event);
     if (ret == -1) {
@@ -1208,7 +1218,7 @@ flb_sockfd_t flb_net_tcp_connect(const char *host, unsigned long port,
     }
 
     if (fd == -1) {
-        flb_error("[net] could not connect to %s:%s",
+        flb_debug("[net] could not connect to %s:%s",
                   host, _port);
     }
 
diff --git a/src/flb_upstream.c b/src/flb_upstream.c
index bbc83556fce..99ff826a2bc 100644
--- a/src/flb_upstream.c
+++ b/src/flb_upstream.c
@@ -209,6 +209,7 @@ struct flb_upstream *flb_upstream_create(struct flb_config *config,
         flb_errno();
         return NULL;
     }
+    u->config = config;
 
     /* Set default networking setup values */
     flb_net_setup_init(&u->net);
@@ -254,7 +255,6 @@ struct flb_upstream *flb_upstream_create(struct flb_config *config,
     u->flags         |= FLB_IO_ASYNC;
     u->thread_safe    = FLB_FALSE;
 
-
     /* Initialize queues */
     flb_upstream_queue_init(&u->queue);
 
@@ -429,15 +429,19 @@ static int prepare_destroy_conn(struct flb_upstream_conn *u_conn)
 static inline int prepare_destroy_conn_safe(struct flb_upstream_conn *u_conn)
 {
     int ret;
+    int locked = FLB_FALSE;
     struct flb_upstream *u = u_conn->u;
 
     if (u->thread_safe == FLB_TRUE) {
-        pthread_mutex_lock(&u->mutex_lists);
+        ret = pthread_mutex_trylock(&u->mutex_lists);
+        if (ret == 0) {
+            locked = FLB_TRUE;
+        }
     }
 
     ret = prepare_destroy_conn(u_conn);
 
-    if (u->thread_safe == FLB_TRUE) {
+    if (locked) {
         pthread_mutex_unlock(&u->mutex_lists);
     }
 
@@ -791,10 +795,13 @@ int flb_upstream_conn_timeouts(struct mk_list *list)
                 u_conn->ts_connect_timeout > 0 &&
                 u_conn->ts_connect_timeout <= now) {
                 drop = FLB_TRUE;
-                flb_error("[upstream] connection #%i to %s:%i timed out after "
-                          "%i seconds",
-                          u_conn->fd,
-                          u->tcp_host, u->tcp_port, u->net.connect_timeout);
+
+                if (!flb_upstream_is_shutting_down(u)) {
+                    flb_error("[upstream] connection #%i to %s:%i timed out after "
+                              "%i seconds",
+                              u_conn->fd,
+                              u->tcp_host, u->tcp_port, u->net.connect_timeout);
+                }
             }
 
             if (drop == FLB_TRUE) {