diff --git a/include/fluent-bit/flb_connection.h b/include/fluent-bit/flb_connection.h
index b2d1e48c6a4..46fd80c4bad 100644
--- a/include/fluent-bit/flb_connection.h
+++ b/include/fluent-bit/flb_connection.h
@@ -95,6 +95,14 @@ struct flb_connection {
      */
     int busy_flag;
 
+    /* This flag is used to determine if the connection was shut down to ensure we
+     * don't do it twice when a timeout is detected.
+     *
+     * This is required in order to overcome a limitation in the async read / write
+     * functions that will be addressed as soon as possible.
+     */
+    int shutdown_flag;
+
     /*
      * Recycle: if the connection is keepalive, this flag is always on, but if
      * the caller wants to drop the connection once is released, it can set
diff --git a/src/flb_connection.c b/src/flb_connection.c
index 051a6c9a305..a3ed402651b 100644
--- a/src/flb_connection.c
+++ b/src/flb_connection.c
@@ -24,6 +24,8 @@ int flb_connection_setup(struct flb_connection *connection,
     connection->tls_session             = NULL;
     connection->ts_created              = time(NULL);
     connection->ts_assigned             = time(NULL);
+    connection->busy_flag               = FLB_FALSE;
+    connection->shutdown_flag           = FLB_FALSE;
 
     connection->net = &connection->stream->net;
 
diff --git a/src/flb_upstream.c b/src/flb_upstream.c
index 4701cc3d68f..142f9680396 100644
--- a/src/flb_upstream.c
+++ b/src/flb_upstream.c
@@ -437,6 +437,23 @@ struct flb_upstream *flb_upstream_create_url(struct flb_config *config,
     return u;
 }
 
+/* This function shuts the connection down in order to cause
+ * any client code trying to read or write from it to fail.
+ */
+static void shutdown_connection(struct flb_connection *u_conn)
+{
+    struct flb_upstream *u;
+
+    u = u_conn->upstream;
+
+    if (u_conn->fd > 0 &&
+        !u_conn->shutdown_flag) {
+        shutdown(u_conn->fd, SHUT_RDWR);
+
+        u_conn->shutdown_flag = FLB_TRUE;
+    }
+}
+
 /*
  * This function moves the 'upstream connection' into the queue to be
  * destroyed. Note that the caller is responsible to validate and check
@@ -462,13 +479,18 @@ static int prepare_destroy_conn(struct flb_connection *u_conn)
 #ifdef FLB_HAVE_TLS
         if (u_conn->tls_session != NULL) {
             flb_tls_session_destroy(u_conn->tls_session);
+
+            u_conn->tls_session = NULL;
         }
 #endif
-        shutdown(u_conn->fd, SHUT_RDWR);
+        shutdown_connection(u_conn);
+
         flb_socket_close(u_conn->fd);
+
         u_conn->fd = -1;
         u_conn->event.fd = -1;
     }
+
     /* remove connection from the queue */
     mk_list_del(&u_conn->_head);
 
@@ -843,7 +865,6 @@ int flb_upstream_conn_timeouts(struct mk_list *list)
 {
     time_t now;
     int drop;
-    int inject;
     const char *reason;
     struct mk_list *head;
     struct mk_list *u_head;
@@ -904,18 +925,53 @@ int flb_upstream_conn_timeouts(struct mk_list *list)
                     }
                 }
 
-                inject = FLB_FALSE;
-                if (u_conn->event.status != MK_EVENT_NONE) {
-                    inject = FLB_TRUE;
-                }
                 u_conn->net_error = ETIMEDOUT;
-                prepare_destroy_conn(u_conn);
-                if (inject == FLB_TRUE) {
+
+                /* We need to shut the connection down
+                 * in order to cause some functions that are not
+                 * aware of the connection error signaling
+                 * mechanism to fail and abort.
+                 *
+                 * These functions do not check the net_error field
+                 * in the connection instance upon being awakened
+                 * so we need to ensure that any read/write
+                 * operations on the socket generate an error.
+                 *
+                 * net_io_write_async
+                 * net_io_read_async
+                 * flb_tls_net_write_async
+                 * flb_tls_net_read_async
+                 *
+                 * This operation could be selectively performed for
+                 * connections that have already been established
+                 * with no side effects because the connection
+                 * establishment code honors `net_error` but
+                 * taking in account that the previous version of
+                 * the code did it unconditionally with no noticeable
+                 * side effects leaving it that way is the safest
+                 * choice at the moment.
+                 */
+
+                if (MK_EVENT_IS_REGISTERED((&u_conn->event))) {
+                    shutdown_connection(u_conn);
+
                     mk_event_inject(u_conn->evl,
                                     &u_conn->event,
                                     u_conn->event.mask,
                                     FLB_TRUE);
                 }
+                else {
+                    /* I can't think of a valid reason for this code path
+                     * to be taken but considering that it was previously
+                     * possible for it to happen (maybe wesley can shed
+                     * some light on it if he remembers) I'll leave this
+                     * for the moment.
+                     * In any case, it's proven not to interfere with the
+                     * coroutine awakening issue this change addresses.
+                     */
+
+                    prepare_destroy_conn(u_conn);
+                }
 
                 flb_upstream_decrement_busy_connections_count(u);
             }