diff --git a/caddyconfig/httpcaddyfile/directives.go b/caddyconfig/httpcaddyfile/directives.go
index e93fdd03..d6af97da 100644
--- a/caddyconfig/httpcaddyfile/directives.go
+++ b/caddyconfig/httpcaddyfile/directives.go
@@ -398,6 +398,14 @@ func sortRoutes(routes []ConfigValue) {
 		if len(jPM) > 0 {
 			jPathLen = len(jPM[0])
 		}
+
+		// if both directives have no path matcher, use whichever one
+		// has any kind of matcher defined first.
+		if iPathLen == 0 && jPathLen == 0 {
+			return len(iRoute.MatcherSetsRaw) > 0 && len(jRoute.MatcherSetsRaw) == 0
+		}
+
+		// sort with the most-specific (longest) path first
 		return iPathLen > jPathLen
 	})
 }
diff --git a/caddytest/integration/caddyfile_adapt/sort_directives_with_any_matcher_first.txt b/caddytest/integration/caddyfile_adapt/sort_directives_with_any_matcher_first.txt
new file mode 100644
index 00000000..d15f56bf
--- /dev/null
+++ b/caddytest/integration/caddyfile_adapt/sort_directives_with_any_matcher_first.txt
@@ -0,0 +1,55 @@
+:80
+
+file_server
+
+@untrusted not remote_ip 10.1.1.0/24
+file_server @untrusted
+----------
+{
+	"apps": {
+		"http": {
+			"servers": {
+				"srv0": {
+					"listen": [
+						":80"
+					],
+					"routes": [
+						{
+							"match": [
+								{
+									"not": [
+										{
+											"remote_ip": {
+												"ranges": [
+													"10.1.1.0/24"
+												]
+											}
+										}
+									]
+								}
+							],
+							"handle": [
+								{
+									"handler": "file_server",
+									"hide": [
+										"Caddyfile"
+									]
+								}
+							]
+						},
+						{
+							"handle": [
+								{
+									"handler": "file_server",
+									"hide": [
+										"Caddyfile"
+									]
+								}
+							]
+						}
+					]
+				}
+			}
+		}
+	}
+}
\ No newline at end of file