diff --git a/antlr-kotlin-tests/antlr/BracketsParser.g4 b/antlr-kotlin-tests/antlr/BracketsParser.g4
new file mode 100644
index 00000000..4580a3b7
--- /dev/null
+++ b/antlr-kotlin-tests/antlr/BracketsParser.g4
@@ -0,0 +1,15 @@
+parser grammar BracketsParser;
+
+tokens {
+  LEFT, RIGHT
+}
+
+options {
+  TokenLabelType=BracketToken;
+}
+
+@header {
+  import com.strumenta.antlrkotlin.test.BracketToken
+}
+
+matched: left=LEFT matched* left=RIGHT;
\ No newline at end of file
diff --git a/antlr-kotlin-tests/src/commonMain/kotlin/com/strumenta/antlrkotlin/test/BracketToken.kt b/antlr-kotlin-tests/src/commonMain/kotlin/com/strumenta/antlrkotlin/test/BracketToken.kt
new file mode 100644
index 00000000..4305df9d
--- /dev/null
+++ b/antlr-kotlin-tests/src/commonMain/kotlin/com/strumenta/antlrkotlin/test/BracketToken.kt
@@ -0,0 +1,9 @@
+package com.strumenta.antlrkotlin.test
+
+import org.antlr.v4.kotlinruntime.CommonToken
+import org.antlr.v4.kotlinruntime.Token
+
+public sealed interface BracketToken : Token {
+  public class Left(text: String) : CommonToken(1, text), BracketToken
+  public class Right(text: String) : CommonToken(2, text), BracketToken
+}
\ No newline at end of file
diff --git a/antlr-kotlin-tests/src/commonTest/kotlin/com/strumenta/antlrkotlin/test/grammars/BracketsTest.kt b/antlr-kotlin-tests/src/commonTest/kotlin/com/strumenta/antlrkotlin/test/grammars/BracketsTest.kt
new file mode 100644
index 00000000..753e444e
--- /dev/null
+++ b/antlr-kotlin-tests/src/commonTest/kotlin/com/strumenta/antlrkotlin/test/grammars/BracketsTest.kt
@@ -0,0 +1,41 @@
+package com.strumenta.antlrkotlin.test.grammars
+
+import com.strumenta.antlrkotlin.test.BracketToken.Left
+import com.strumenta.antlrkotlin.test.BracketToken.Right
+import com.strumenta.antlrkotlin.test.ThrowingErrorListener
+import com.strumenta.antlrkotlin.test.generated.BracketsParser
+import com.strumenta.antlrkotlin.util.loadResourceText
+import org.antlr.v4.kotlinruntime.ListTokenSource
+import org.antlr.v4.kotlinruntime.UnbufferedTokenStream
+import org.antlr.v4.kotlinruntime.tree.Trees
+import kotlin.test.Test
+import kotlin.test.assertEquals
+
+@Suppress("unused")
+class BracketsTest {
+
+  @Test
+  fun parsesMatched() {
+    // Create the parser
+    val tokenStream = UnbufferedTokenStream(
+      ListTokenSource(
+        listOf(
+          Left("("), Left("["), Right("]"),
+          Left("{"), Right("}"), Right(")")
+        )
+      )
+    )
+    val parser = BracketsParser(tokenStream)
+    parser.addErrorListener(ThrowingErrorListener)
+    val tree = parser.matched()
+    val lispTree = Trees.toStringTree(tree, parser)
+
+    val expectedLispTreeText = loadResourceText("src/commonTest/resources/brackets/matched.tree")
+
+    assertEquals(
+      expected = expectedLispTreeText,
+      actual = lispTree,
+      message = "Outputted LISP tree does not match the expected tree",
+    )
+  }
+}
diff --git a/antlr-kotlin-tests/src/commonTest/resources/brackets/matched.tree b/antlr-kotlin-tests/src/commonTest/resources/brackets/matched.tree
new file mode 100644
index 00000000..fe00111f
--- /dev/null
+++ b/antlr-kotlin-tests/src/commonTest/resources/brackets/matched.tree
@@ -0,0 +1 @@
+(matched ( (matched [ ]) (matched { }) ))
\ No newline at end of file