diff --git a/net/ipv4/udp.c b/net/ipv4/udp.c
index 3f9c4b74fdc0c7246faa62eec09feb2b0b60a4d3..88da11922d677d927f8c4b78ec554113f22ae17a 100644
--- a/net/ipv4/udp.c
+++ b/net/ipv4/udp.c
@@ -939,9 +939,9 @@ 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 f55d08d2096ae9d7a8b152c7d63bac0a2f469699..4b063aa37e389963ddda8f07da2a3222012063cd 100644
--- a/net/ipv6/udp.c
+++ b/net/ipv6/udp.c
@@ -1256,9 +1256,9 @@ 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 b02080d09fbc057e2e7e136a1de345e51ae52042..d0fba50bd6ef085440de8ce800b0fc6216c5c6aa 100644
--- a/tools/testing/selftests/net/udpgso.c
+++ b/tools/testing/selftests/net/udpgso.c
@@ -94,6 +94,19 @@ 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,
@@ -197,6 +210,19 @@ 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,