diff --git a/util/cmpver/version_test.go b/util/cmpver/version_test.go
index b3ab1b028..8f13fabf6 100644
--- a/util/cmpver/version_test.go
+++ b/util/cmpver/version_test.go
@@ -91,6 +91,12 @@ func TestCompare(t *testing.T) {
 			v2:   "0.96-105",
 			want: 1,
 		},
+		{
+			name: "tailscale-three-digits",
+			v1:   "1.100.2",
+			v2:   "1.55.0",
+			want: 1,
+		},
 		{
 			// Though ۱ and ۲ both satisfy unicode.IsNumber, our previous use
 			// of strconv.ParseUint with these characters would have lead us to