diff --git a/lib/web/app/transport.go b/lib/web/app/transport.go
index a25e8c0c9b8a8..408cf0a24c8da 100644
--- a/lib/web/app/transport.go
+++ b/lib/web/app/transport.go
@@ -386,12 +386,18 @@ func (t *transport) DialContext(ctx context.Context, _, _ string) (conn net.Conn
 		break
 	}
 
-	// eliminate any servers from the head of the list that were unreachable
 	t.mu.Lock()
-	if i < len(servers) {
-		t.c.servers = t.c.servers[i:]
-	} else {
-		t.c.servers = nil
+	// Only attempt to tidy up the list of servers if they weren't altered
+	// while the dialing happened. Since the lock is only held initially when
+	// making the servers copy and released during the dials, another dial attempt
+	// may have already happened and modified the list of servers.
+	if len(servers) == len(t.c.servers) {
+		// eliminate any servers from the head of the list that were unreachable
+		if i < len(t.c.servers) {
+			t.c.servers = t.c.servers[i:]
+		} else {
+			t.c.servers = nil
+		}
 	}
 	t.mu.Unlock()