diff --git a/test-tests/shared/src/test/scala/zio/test/DefaultTestReporterSpec.scala b/test-tests/shared/src/test/scala/zio/test/DefaultTestReporterSpec.scala
index 33436f25382a..5b756b6a1fec 100644
--- a/test-tests/shared/src/test/scala/zio/test/DefaultTestReporterSpec.scala
+++ b/test-tests/shared/src/test/scala/zio/test/DefaultTestReporterSpec.scala
@@ -40,6 +40,11 @@ object DefaultTestReporterSpec extends ZIOBaseSpec {
       test("correctly reports labeled failures") {
         assertM(runLog(test7))(equalTo(test7Expected.mkString + "\n" + reportStats(0, 0, 1)))
       },
+      test("correctly reports labeled failures for assertTrue") {
+        for {
+          log <- runLog(test9)
+        } yield assertTrue(log.contains("""?? "third""""), log.contains("""?? "fourth""""))
+      },
       test("correctly reports negated failures") {
         assertM(runLog(test8))(equalTo(test8Expected.mkString + "\n" + reportStats(0, 0, 1)))
       }
diff --git a/test-tests/shared/src/test/scala/zio/test/ReportingTestUtils.scala b/test-tests/shared/src/test/scala/zio/test/ReportingTestUtils.scala
index 99a4a72c6bab..add6650ccd57 100644
--- a/test-tests/shared/src/test/scala/zio/test/ReportingTestUtils.scala
+++ b/test-tests/shared/src/test/scala/zio/test/ReportingTestUtils.scala
@@ -156,6 +156,13 @@ object ReportingTestUtils {
     withOffset(2)(assertSourceLocation() + "\n")
   )
 
+  def test9(implicit trace: ZTraceElement): ZSpec[Any, Nothing] = test("labeled failures") {
+    assertTrue(1 == 1).map(_.label("first")) &&
+    assertTrue(1 == 1).map(_.label("second")) &&
+    assertTrue(1 == 0).map(_.label("third")) &&
+    assertTrue(1 == 0).map(_.label("fourth"))
+  }
+
   def suite1(implicit trace: ZTraceElement): Spec[Any, TestFailure[Nothing], TestSuccess] =
     suite("Suite1")(test1, test2)
   def suite1Expected(implicit trace: ZTraceElement): Vector[String] = Vector(
diff --git a/test/shared/src/main/scala/zio/test/AssertionResult.scala b/test/shared/src/main/scala/zio/test/AssertionResult.scala
index e8d938f1945f..1baef150e87d 100644
--- a/test/shared/src/main/scala/zio/test/AssertionResult.scala
+++ b/test/shared/src/main/scala/zio/test/AssertionResult.scala
@@ -12,7 +12,7 @@ sealed trait AssertionResult { self =>
       case result: FailureDetailsResult =>
         result.copy(failureDetails = result.failureDetails.label(label))
       case result: AssertionResult.TraceResult =>
-        result
+        result.copy(label = Some(label))
     }
 
   def setGenFailureDetails(details: GenFailureDetails): AssertionResult =
@@ -27,6 +27,9 @@ sealed trait AssertionResult { self =>
 object AssertionResult {
   case class FailureDetailsResult(failureDetails: FailureDetails, genFailureDetails: Option[GenFailureDetails] = None)
       extends AssertionResult
-  case class TraceResult(trace: Trace[Boolean], genFailureDetails: Option[GenFailureDetails] = None)
-      extends AssertionResult
+  case class TraceResult(
+    trace: Trace[Boolean],
+    genFailureDetails: Option[GenFailureDetails] = None,
+    label: Option[String] = None
+  ) extends AssertionResult
 }
diff --git a/test/shared/src/main/scala/zio/test/DefaultTestReporter.scala b/test/shared/src/main/scala/zio/test/DefaultTestReporter.scala
index 5a1e385a77ea..11b125937b9a 100644
--- a/test/shared/src/main/scala/zio/test/DefaultTestReporter.scala
+++ b/test/shared/src/main/scala/zio/test/DefaultTestReporter.scala
@@ -85,10 +85,10 @@ object DefaultTestReporter {
               result
                 .fold[Option[TestResult]] {
                   case result: AssertionResult.FailureDetailsResult => Some(BoolAlgebra.success(result))
-                  case AssertionResult.TraceResult(trace, genFailureDetails) =>
+                  case AssertionResult.TraceResult(trace, genFailureDetails, label) =>
                     Trace
                       .prune(trace, false)
-                      .map(a => BoolAlgebra.success(AssertionResult.TraceResult(a, genFailureDetails)))
+                      .map(a => BoolAlgebra.success(AssertionResult.TraceResult(a, genFailureDetails, label)))
                 }(
                   {
                     case (Some(a), Some(b)) => Some(a && b)
@@ -185,12 +185,12 @@ object DefaultTestReporter {
 
   def renderAssertionResult(assertionResult: AssertionResult, offset: Int): Message =
     assertionResult match {
-      case AssertionResult.TraceResult(trace, genFailureDetails) =>
+      case AssertionResult.TraceResult(trace, genFailureDetails, label) =>
         val failures = FailureCase.fromTrace(trace)
         failures
           .map(fc =>
             renderGenFailureDetails(genFailureDetails, offset) ++
-              Message(renderFailureCase(fc, offset))
+              Message(renderFailureCase(fc, offset, label))
           )
           .foldLeft(Message.empty)(_ ++ _)
 
@@ -199,7 +199,7 @@ object DefaultTestReporter {
           renderFailureDetails(failureDetails, offset)
     }
 
-  def renderFailureCase(failureCase: FailureCase, offset: Int): Chunk[Line] =
+  def renderFailureCase(failureCase: FailureCase, offset: Int, testLabel: Option[String]): Chunk[Line] =
     failureCase match {
       case FailureCase(errorMessage, codeString, location, path, _, nested, _) =>
         val errorMessageLines =
@@ -210,8 +210,8 @@ object DefaultTestReporter {
 
         val result =
           errorMessageLines ++
-            Chunk(Line.fromString(codeString)) ++
-            nested.flatMap(renderFailureCase(_, offset)).map(_.withOffset(1)) ++
+            Chunk(Line.fromString(testLabel.fold(codeString)(l => s"""$codeString ?? "$l""""))) ++
+            nested.flatMap(renderFailureCase(_, offset, None)).map(_.withOffset(1)) ++
             Chunk.fromIterable(path.flatMap { case (label, value) =>
               Chunk.fromIterable(PrettyPrint(value).split("\n").map(primary(_).toLine)) match {
                 case head +: lines => (dim(s"${label.trim} = ") +: head) +: lines