diff --git a/caddyconfig/httpcaddyfile/directives.go b/caddyconfig/httpcaddyfile/directives.go
index f411aabe3..e8ad62d22 100644
--- a/caddyconfig/httpcaddyfile/directives.go
+++ b/caddyconfig/httpcaddyfile/directives.go
@@ -465,6 +465,15 @@ func sortRoutes(routes []ConfigValue, order []string) {
 			return dirPositions[iDir] < dirPositions[jDir]
 		}
 
+		// some directives involve setting values which can overwrite
+		// each other, so it makes most sense to reverse the order so
+		// that the least-specific matcher is first, allowing the last
+		// matching one to win; we swap i and j instead of using !,
+		// so matchers that can't be compared keep their order
+		if iDir == "vars" {
+			i, j = j, i
+		}
+
 		// directives are the same; sub-sort by path matcher length if there's
 		// only one matcher set and one path (this is a very common case and
 		// usually -- but not always -- helpful/expected, oh well; user can
@@ -535,15 +544,7 @@ func sortRoutes(routes []ConfigValue, order []string) {
 			return len(iRoute.MatcherSetsRaw) > 0 && len(jRoute.MatcherSetsRaw) == 0
 		}()
 
-		// some directives involve setting values which can overwrite
-		// each other, so it makes most sense to reverse the order so
-		// that the least-specific matcher is first, allowing the last
-		// matching one to win
-		if iDir == "vars" {
-			return !sortByPath
-		}
-
-		// everything else is most-specific matcher first
+		// most-specific matcher first (or last for vars, see above)
 		return sortByPath
 	})
 }
diff --git a/caddytest/integration/caddyfile_adapt/map_and_vars_with_raw_types.caddyfiletest b/caddytest/integration/caddyfile_adapt/map_and_vars_with_raw_types.caddyfiletest
index 8b872635d..6c9ade715 100644
--- a/caddytest/integration/caddyfile_adapt/map_and_vars_with_raw_types.caddyfiletest
+++ b/caddytest/integration/caddyfile_adapt/map_and_vars_with_raw_types.caddyfiletest
@@ -101,16 +101,16 @@ vars {
 													],
 													"source": "{http.request.host}"
 												},
+												{
+													"foo": "bar",
+													"handler": "vars"
+												},
 												{
 													"abc": true,
 													"def": 1,
 													"ghi": 2.3,
 													"handler": "vars",
 													"jkl": "mn op"
-												},
-												{
-													"foo": "bar",
-													"handler": "vars"
 												}
 											]
 										}
diff --git a/caddytest/integration/caddyfile_adapt/sort_vars_named_matchers_keep_order.caddyfiletest b/caddytest/integration/caddyfile_adapt/sort_vars_named_matchers_keep_order.caddyfiletest
new file mode 100644
index 000000000..724804180
--- /dev/null
+++ b/caddytest/integration/caddyfile_adapt/sort_vars_named_matchers_keep_order.caddyfiletest
@@ -0,0 +1,63 @@
+:80
+
+@first header X-Test a
+@second header X-Test a
+@third header X-Other b
+
+vars @first value first
+vars @second value second
+vars @third value third
+----------
+{
+	"apps": {
+		"http": {
+			"servers": {
+				"srv0": {
+					"listen": [
+						":80"
+					],
+					"routes": [
+						{
+							"match": [
+								{
+									"header": {
+										"X-Test": [
+											"a"
+										]
+									}
+								}
+							],
+							"handle": [
+								{
+									"handler": "vars",
+									"value": "first"
+								},
+								{
+									"handler": "vars",
+									"value": "second"
+								}
+							]
+						},
+						{
+							"match": [
+								{
+									"header": {
+										"X-Other": [
+											"b"
+										]
+									}
+								}
+							],
+							"handle": [
+								{
+									"handler": "vars",
+									"value": "third"
+								}
+							]
+						}
+					]
+				}
+			}
+		}
+	}
+}