diff --git a/matcher/shared/src/main/scala/org/specs2/matcher/TryMatchers.scala b/matcher/shared/src/main/scala/org/specs2/matcher/TryMatchers.scala
index 847302ed57..8b84e1191f 100644
--- a/matcher/shared/src/main/scala/org/specs2/matcher/TryMatchers.scala
+++ b/matcher/shared/src/main/scala/org/specs2/matcher/TryMatchers.scala
@@ -3,6 +3,7 @@ package matcher
 
 import scala.reflect.ClassTag
 import util.*
+import execute.{Result, AsResult}
 import execute.ResultImplicits.*
 import org.specs2.matcher.describe.Diffable
 import text.NotNullStrings.*
@@ -45,11 +46,17 @@ trait TryMatchers:
 
 object TryeMatchers extends TryMatchers
 
-case class TrySuccessMatcher[T]() extends OptionLikeMatcher[Try[T], T]("a Success", (_: Try[T]).toOption):
-  def withValue(t: ValueCheck[T]) = TrySuccessCheckedMatcher(t)
+case class TrySuccessMatcher[T]() extends Matcher[Try[T]]:
+  def apply[S <: Try[T]](value: Expectable[S]): Result = checkSuccess(value, ValueCheck.alwaysOk)
 
-case class TrySuccessCheckedMatcher[T](check: ValueCheck[T])
-    extends OptionLikeCheckedMatcher[Try[T], T]("a Success", (_: Try[T]).toOption, check)
+  def withValue(t: ValueCheck[T]): Matcher[Try[T]] = TrySuccessCheckedMatcher(t)
+
+  def which[R: AsResult](f: T => R): Matcher[Try[T]] = new TrySuccessCheckedMatcher(f)
+
+  def like[R: AsResult](f: PartialFunction[T, R]): Matcher[Try[T]] = new TrySuccessCheckedMatcher(f)
+
+case class TrySuccessCheckedMatcher[T](check: ValueCheck[T]) extends Matcher[Try[T]]:
+  def apply[S <: Try[T]](value: Expectable[S]): Result = checkSuccess(value, check)
 
 case class TryFailureMatcher[T]()
     extends OptionLikeMatcher[Try[T], Throwable]("a Failure", (_: Try[T]).failed.toOption):
@@ -65,3 +72,15 @@ case class TryFailureMatcher[T]()
   })
 case class TryFailureCheckedMatcher[T](check: ValueCheck[Throwable])
     extends OptionLikeCheckedMatcher[Try[T], Throwable]("a Failure", (_: Try[T]).failed.toOption, check)
+
+private def checkSuccess[T](value: Expectable[Try[T]], check: ValueCheck[T]): Result = value.value match
+  case Success(v) =>
+    val r = check.check(v)
+    val koMessage = s"${value.description} is a Success but ${r.message}"
+    r match
+      case execute.Failure(_, _, _, details) => Result.result(false, koMessage, details)
+      case _                                 => Result.result(r.isSuccess, koMessage)
+  case Failure(e) =>
+    execute.Failure(
+      s"${value.description} is not a Success\n\nFailed with ${e.getMessage}:\n\n${e.getStackTrace.mkString("\n")}"
+    )
diff --git a/tests/shared/src/test/scala/org/specs2/matcher/TryMatchersSpec.scala b/tests/shared/src/test/scala/org/specs2/matcher/TryMatchersSpec.scala
index d77910ea53..695a31e34b 100644
--- a/tests/shared/src/test/scala/org/specs2/matcher/TryMatchersSpec.scala
+++ b/tests/shared/src/test/scala/org/specs2/matcher/TryMatchersSpec.scala
@@ -18,14 +18,14 @@ class TryMatchersSpec extends Spec with TryMatchers with ResultMatchers {
   ${(Succeeded(1) must beASuccessfulTry.which(_ > 0))}
   ${(Succeeded(1) must beASuccessfulTry
     .which(_ < 0)) returns "Success(1) is a Success but the function returns 'false' on '1'"}
-  ${(Failed[I](e) must beASuccessfulTry.which(_ > 0)) returns "Failure(boom) is not a Success"}
+  ${(Failed[I](e) must beASuccessfulTry.which(_ > 0)) returns "Failure(boom) is not a Success\n\nFailed with boom:\n\n"}
 
   ${Succeeded(1) must beASuccessfulTry[Int].like { case a if a > 0 => ok }}
   ${(Succeeded(1) must not(beASuccessfulTry[Int].like { case a => a must be_>=(0) })) returns "Expectation failed: 'Success(1) is a Success but 1 is strictly less than 0'"}
   ${Succeeded(1) must not(beASuccessfulTry.withValue(2))}
   ${Failed[I](e) must not(beASuccessfulTry)}
   ${Failed[I](e) must not(beASuccessfulTry.withValue(2))}
-  ${(Failed[I](e) must beSuccessfulTry) returns "Failure(boom) is not a Success"}
+  ${(Failed[I](e) must beSuccessfulTry) returns "Failure(boom) is not a Success\n\nFailed with boom:\n\n"}
   ${(Succeeded(1) must beSuccessfulTry.withValue(2)) returns "Success(1) is a Success but 1 != 2"}
 
   beAFailure checks if an element is Failure(_)