diff --git a/net/ipv4/tcp_output.c b/net/ipv4/tcp_output.c
index dda42f0bd7a3..f5263c840338 100644
--- a/net/ipv4/tcp_output.c
+++ b/net/ipv4/tcp_output.c
@@ -663,10 +663,14 @@ static int tcp_transmit_skb(struct sock *sk, struct sk_buff *skb, int clone_it,
 	th->urg_ptr		= 0;
 
 	/* The urg_mode check is necessary during a below snd_una win probe */
-	if (unlikely(tcp_urg_mode(tp) &&
-		     between(tp->snd_up, tcb->seq + 1, tcb->seq + 0xFFFF))) {
-		th->urg_ptr		= htons(tp->snd_up - tcb->seq);
-		th->urg			= 1;
+	if (unlikely(tcp_urg_mode(tp) && before(tcb->seq, tp->snd_up))) {
+		if (before(tp->snd_up, tcb->seq + 0x10000)) {
+			th->urg_ptr = htons(tp->snd_up - tcb->seq);
+			th->urg = 1;
+		} else if (after(tcb->seq + 0xFFFF, tp->snd_nxt)) {
+			th->urg_ptr = 0xFFFF;
+			th->urg = 1;
+		}
 	}
 
 	tcp_options_write((__be32 *)(th + 1), tp, &opts, &md5_hash_location);