diff --git a/exercises/practice/matching-brackets/.meta/tests.toml b/exercises/practice/matching-brackets/.meta/tests.toml
index cc9e471a..35a98a04 100644
--- a/exercises/practice/matching-brackets/.meta/tests.toml
+++ b/exercises/practice/matching-brackets/.meta/tests.toml
@@ -1,6 +1,13 @@
-# This is an auto-generated file. Regular comments will be removed when this
-# file is regenerated. Regenerating will not touch any manually added keys,
-# so comments can be added in a "comment" key.
+# This is an auto-generated file.
+#
+# Regenerating this file via `configlet sync` will:
+# - Recreate every `description` key/value pair
+# - Recreate every `reimplements` key/value pair, where they exist in problem-specifications
+# - Remove any `include = true` key/value pair (an omitted `include` key implies inclusion)
+# - Preserve any other key/value pair
+#
+# As user-added comments (using the # character) will be removed when this file
+# is regenerated, comments can be added via a `comment` key.
 
 [81ec11da-38dd-442a-bcf9-3de7754609a5]
 description = "paired square brackets"
@@ -41,12 +48,21 @@ description = "unpaired and nested brackets"
 [a0205e34-c2ac-49e6-a88a-899508d7d68e]
 description = "paired and wrong nested brackets"
 
+[1d5c093f-fc84-41fb-8c2a-e052f9581602]
+description = "paired and wrong nested brackets but innermost are correct"
+
 [ef47c21b-bcfd-4998-844c-7ad5daad90a8]
 description = "paired and incomplete brackets"
 
 [a4675a40-a8be-4fc2-bc47-2a282ce6edbe]
 description = "too many closing brackets"
 
+[a345a753-d889-4b7e-99ae-34ac85910d1a]
+description = "early unexpected brackets"
+
+[21f81d61-1608-465a-b850-baa44c5def83]
+description = "early mismatched brackets"
+
 [99255f93-261b-4435-a352-02bdecc9bdf2]
 description = "math expression"
 
diff --git a/exercises/practice/matching-brackets/matching_brackets_test.cpp b/exercises/practice/matching-brackets/matching_brackets_test.cpp
index c0b4f715..a0d76dfe 100644
--- a/exercises/practice/matching-brackets/matching_brackets_test.cpp
+++ b/exercises/practice/matching-brackets/matching_brackets_test.cpp
@@ -42,6 +42,18 @@ TEST_CASE("unpaired_nested_brackets") {
     REQUIRE(!matching_brackets::check("([{])"));
 }
 
+TEST_CASE("paired_and_wrong_nested_brackets_but_innermost_are_correct") {
+    REQUIRE(!matching_brackets::check("[({}])"));
+}
+
+TEST_CASE("early_unexpected_brackets") {
+    REQUIRE(!matching_brackets::check(")()"));
+}
+
+TEST_CASE("early_mismatched_brackets") {
+    REQUIRE(!matching_brackets::check("{)()"));
+}
+
 TEST_CASE("paired_wrong_nested_brackets") {
     REQUIRE(!matching_brackets::check("[({]})"));
 }