diff --git a/plugin/transfer/transfer.go b/plugin/transfer/transfer.go
index 5adf1c1e2..bbd91b5eb 100644
--- a/plugin/transfer/transfer.go
+++ b/plugin/transfer/transfer.go
@@ -209,7 +209,7 @@ func longestMatch(xfrs []*xfr, name string) *xfr {
 	zone := "" // longest zone match wins
 	for _, xfr := range xfrs {
 		if z := plugin.Zones(xfr.Zones).Matches(name); z != "" {
-			if z > zone {
+			if len(z) > len(zone) || (len(z) == len(zone) && z > zone) {
 				zone = z
 				x = xfr
 			}
diff --git a/plugin/transfer/transfer_test.go b/plugin/transfer/transfer_test.go
index 04ea6f8b5..2bf75ce07 100644
--- a/plugin/transfer/transfer_test.go
+++ b/plugin/transfer/transfer_test.go
@@ -369,3 +369,22 @@ func TestAXFRZoneMatchCaseInsensitive(t *testing.T) {
 
 	validateAXFRResponse(t, w)
 }
+
+func TestLongestMatchMostSpecificZone(t *testing.T) {
+	x1 := &xfr{Zones: []string{"example.org."}}
+	x2 := &xfr{Zones: []string{"a.example.org."}}
+
+	got := longestMatch([]*xfr{x1, x2}, "host.a.example.org.")
+	if got != x2 {
+		t.Fatalf("expected most specific zone (a.example.org.) to match, got %+v", got)
+	}
+}
+
+func TestLongestMatchNilWhenNoMatch(t *testing.T) {
+	x1 := &xfr{Zones: []string{"example.org."}}
+
+	got := longestMatch([]*xfr{x1}, "other.net.")
+	if got != nil {
+		t.Fatalf("expected nil when no zones match, got %+v", got)
+	}
+}