diff --git a/server/handlers/validation.go b/server/handlers/validation.go
index da974d1ad9..106f940d31 100644
--- a/server/handlers/validation.go
+++ b/server/handlers/validation.go
@@ -139,10 +139,10 @@ func loadAndValidateTargets(gun string, repo *tuf.Repo, roles map[string]storage
 		}
 	}
 
-	// by sorting, we'll always process shallower targets updates before deeper
+	// N.B. RoleList sorts paths with fewer segments first.
+	// By sorting, we'll always process shallower targets updates before deeper
 	// ones (i.e. we'll load and validate targets before targets/foo). This
 	// helps ensure we only load from storage when necessary in a cleaner way.
-	// RoleList sorts paths with fewer segments first
 	sort.Sort(targetsRoles)
 
 	updatesToApply := make([]storage.MetaUpdate, 0, len(targetsRoles))
diff --git a/tuf/utils/role_sort_test.go b/tuf/utils/role_sort_test.go
index b65320885d..8b98f127f7 100644
--- a/tuf/utils/role_sort_test.go
+++ b/tuf/utils/role_sort_test.go
@@ -16,7 +16,7 @@ func TestRoleListLess(t *testing.T) {
 	rl := RoleList{"foo", "foo/bar", "bar/foo"}
 	assert.True(t, rl.Less(0, 1))
 	assert.False(t, rl.Less(1, 2))
-	assert.False(t, rl.Less(2, 1))
+	assert.True(t, rl.Less(2, 1))
 }
 
 func TestRoleListSwap(t *testing.T) {