diff --git a/shared/relay/client/client.go b/shared/relay/client/client.go
index acc5fee0a..c851ab329 100644
--- a/shared/relay/client/client.go
+++ b/shared/relay/client/client.go
@@ -681,6 +681,9 @@ func (c *Client) onDatagramTooLarge(conn net.Conn, cause error) {
 	// Without the shared tracker a reconnect would just race QUIC again and
 	// re-fail, so leave the connection up rather than loop.
 	if c.transportFallback == nil {
+		if c.datagramFallbackTriggered.CompareAndSwap(false, true) {
+			c.log.Debugf("%s, but no transport fallback configured, leaving connection up", cause)
+		}
 		return
 	}
 
diff --git a/shared/relay/client/dialer/race_dialer.go b/shared/relay/client/dialer/race_dialer.go
index 16641f6d0..aef1ef464 100644
--- a/shared/relay/client/dialer/race_dialer.go
+++ b/shared/relay/client/dialer/race_dialer.go
@@ -91,6 +91,9 @@ func (r *RaceDial) Dial(ctx context.Context) (net.Conn, error) {
 // falling back to the next on failure.
 func (r *RaceDial) dialSequential(ctx context.Context) (net.Conn, error) {
 	for _, dfn := range r.dialerFns {
+		if err := ctx.Err(); err != nil {
+			return nil, err
+		}
 		attemptCtx, cancel := context.WithTimeout(ctx, r.connectionTimeout)
 		r.log.Infof("dialing Relay server via %s", dfn.Protocol())
 		conn, err := dfn.Dial(attemptCtx, r.serverURL, r.serverName)