diff --git a/labels/validate.go b/labels/validate.go
index 1fd527adb..f83b5dde2 100644
--- a/labels/validate.go
+++ b/labels/validate.go
@@ -24,15 +24,18 @@ import (
 
 const (
 	maxSize = 4096
+	// maximum length of key portion of error message if len of key + len of value > maxSize
+	keyMaxLen = 64
 )
 
 // Validate a label's key and value are under 4096 bytes
 func Validate(k, v string) error {
-	if (len(k) + len(v)) > maxSize {
-		if len(k) > 10 {
-			k = k[:10]
+	total := len(k) + len(v)
+	if total > maxSize {
+		if len(k) > keyMaxLen {
+			k = k[:keyMaxLen]
 		}
-		return fmt.Errorf("label key and value greater than maximum size (%d bytes), key: %s: %w", maxSize, k, errdefs.ErrInvalidArgument)
+		return fmt.Errorf("label key and value length (%d bytes) greater than maximum size (%d bytes), key: %s: %w", total, maxSize, k, errdefs.ErrInvalidArgument)
 	}
 	return nil
 }
diff --git a/labels/validate_test.go b/labels/validate_test.go
index 1368fc5b7..628f2fd7a 100644
--- a/labels/validate_test.go
+++ b/labels/validate_test.go
@@ -21,6 +21,7 @@ import (
 	"testing"
 
 	"github.com/containerd/containerd/errdefs"
+	"github.com/stretchr/testify/assert"
 )
 
 func TestValidLabels(t *testing.T) {
@@ -51,3 +52,29 @@ func TestInvalidLabels(t *testing.T) {
 		}
 	}
 }
+
+func TestLongKey(t *testing.T) {
+	key := strings.Repeat("s", keyMaxLen+1)
+	value := strings.Repeat("v", maxSize-len(key))
+
+	err := Validate(key, value)
+	assert.Equal(t, err, nil)
+
+	key = strings.Repeat("s", keyMaxLen+12)
+	value = strings.Repeat("v", maxSize-len(key)+1)
+
+	err = Validate(key, value)
+	assert.ErrorIs(t, err, errdefs.ErrInvalidArgument)
+
+	key = strings.Repeat("s", keyMaxLen-1)
+	value = strings.Repeat("v", maxSize-len(key))
+
+	err = Validate(key, value)
+	assert.Equal(t, err, nil)
+
+	key = strings.Repeat("s", keyMaxLen-1)
+	value = strings.Repeat("v", maxSize-len(key)-1)
+
+	err = Validate(key, value)
+	assert.Equal(t, err, nil)
+}