diff --git a/net/ipv4/udp.c b/net/ipv4/udp.c
index d2eeb6fc49b3..8da74dc63061 100644
--- a/net/ipv4/udp.c
+++ b/net/ipv4/udp.c
@@ -985,9 +985,9 @@ static int udp_send_skb(struct sk_buff *skb, struct flowi4 *fl4,
 		const int hlen = skb_network_header_len(skb) +
 				 sizeof(struct udphdr);
 
-		if (hlen + cork->gso_size > cork->fragsize) {
+		if (hlen + min(datalen, cork->gso_size) > cork->fragsize) {
 			kfree_skb(skb);
-			return -EINVAL;
+			return -EMSGSIZE;
 		}
 		if (datalen > cork->gso_size * UDP_MAX_SEGMENTS) {
 			kfree_skb(skb);
diff --git a/net/ipv6/udp.c b/net/ipv6/udp.c
index 896c9c827a28..197d0ac47592 100644
--- a/net/ipv6/udp.c
+++ b/net/ipv6/udp.c
@@ -1294,9 +1294,9 @@ static int udp_v6_send_skb(struct sk_buff *skb, struct flowi6 *fl6,
 		const int hlen = skb_network_header_len(skb) +
 				 sizeof(struct udphdr);
 
-		if (hlen + cork->gso_size > cork->fragsize) {
+		if (hlen + min(datalen, cork->gso_size) > cork->fragsize) {
 			kfree_skb(skb);
-			return -EINVAL;
+			return -EMSGSIZE;
 		}
 		if (datalen > cork->gso_size * UDP_MAX_SEGMENTS) {
 			kfree_skb(skb);
diff --git a/tools/testing/selftests/net/udpgso.c b/tools/testing/selftests/net/udpgso.c
index 3f2fca02fec5..36ff28af4b19 100644
--- a/tools/testing/selftests/net/udpgso.c
+++ b/tools/testing/selftests/net/udpgso.c
@@ -102,6 +102,19 @@ struct testcase testcases_v4[] = {
 		.gso_len = CONST_MSS_V4,
 		.r_num_mss = 1,
 	},
+	{
+		/* datalen <= MSS < gso_len: will fall back to no GSO */
+		.tlen = CONST_MSS_V4,
+		.gso_len = CONST_MSS_V4 + 1,
+		.r_num_mss = 0,
+		.r_len_last = CONST_MSS_V4,
+	},
+	{
+		/* MSS < datalen < gso_len: fail */
+		.tlen = CONST_MSS_V4 + 1,
+		.gso_len = CONST_MSS_V4 + 2,
+		.tfail = true,
+	},
 	{
 		/* send a single MSS + 1B */
 		.tlen = CONST_MSS_V4 + 1,
@@ -205,6 +218,19 @@ struct testcase testcases_v6[] = {
 		.gso_len = CONST_MSS_V6,
 		.r_num_mss = 1,
 	},
+	{
+		/* datalen <= MSS < gso_len: will fall back to no GSO */
+		.tlen = CONST_MSS_V6,
+		.gso_len = CONST_MSS_V6 + 1,
+		.r_num_mss = 0,
+		.r_len_last = CONST_MSS_V6,
+	},
+	{
+		/* MSS < datalen < gso_len: fail */
+		.tlen = CONST_MSS_V6 + 1,
+		.gso_len = CONST_MSS_V6 + 2,
+		.tfail = true
+	},
 	{
 		/* send a single MSS + 1B */
 		.tlen = CONST_MSS_V6 + 1,