diff --git a/action-binding-generator/src/test/kotlin/io/github/typesafegithub/workflows/actionbindinggenerator/Utils.kt b/action-binding-generator/src/test/kotlin/io/github/typesafegithub/workflows/actionbindinggenerator/Utils.kt
index 63f2046cd2..acd65820de 100644
--- a/action-binding-generator/src/test/kotlin/io/github/typesafegithub/workflows/actionbindinggenerator/Utils.kt
+++ b/action-binding-generator/src/test/kotlin/io/github/typesafegithub/workflows/actionbindinggenerator/Utils.kt
@@ -1,7 +1,7 @@
 package io.github.typesafegithub.workflows.actionbindinggenerator
 
 import io.github.typesafegithub.workflows.actionbindinggenerator.generation.ActionBinding
-import io.kotest.assertions.fail
+import io.kotest.matchers.Matcher.Companion.failure
 import io.kotest.matchers.shouldBe
 import java.nio.file.Paths
 
@@ -27,10 +27,11 @@ fun List<ActionBinding>.shouldContainAndMatchFile(path: String) {
         actualContent shouldBe expectedContent
     } else if (actualContent != expectedContent) {
         file.writeText(actualContent)
-        fail(
-            "The binding's Kotlin code in ${file.name} doesn't match the expected one.\n" +
-                "The file has been updated to match what's expected.",
-        )
+        actualContent shouldBe
+            failure<Nothing>(
+                "The binding's Kotlin code in ${file.name} doesn't match the expected one.\n" +
+                    "The file has been updated to match what's expected.",
+            )
     }
 }
 
diff --git a/action-binding-generator/src/test/kotlin/io/github/typesafegithub/workflows/actionbindinggenerator/generation/GenerationTest.kt b/action-binding-generator/src/test/kotlin/io/github/typesafegithub/workflows/actionbindinggenerator/generation/GenerationTest.kt
index f7769c10d0..4e08800962 100644
--- a/action-binding-generator/src/test/kotlin/io/github/typesafegithub/workflows/actionbindinggenerator/generation/GenerationTest.kt
+++ b/action-binding-generator/src/test/kotlin/io/github/typesafegithub/workflows/actionbindinggenerator/generation/GenerationTest.kt
@@ -16,6 +16,7 @@ import io.github.typesafegithub.workflows.actionbindinggenerator.typing.IntegerW
 import io.github.typesafegithub.workflows.actionbindinggenerator.typing.ListOfTypings
 import io.github.typesafegithub.workflows.actionbindinggenerator.typing.StringTyping
 import io.github.typesafegithub.workflows.actionbindinggenerator.typing.Typing
+import io.kotest.assertions.assertSoftly
 import io.kotest.core.spec.style.FunSpec
 import io.kotest.matchers.collections.shouldHaveSize
 
@@ -221,8 +222,10 @@ class GenerationTest :
                 )
 
             // then
-            binding.shouldContainAndMatchFile("ActionWithAllTypesOfInputs.kt")
-            binding.shouldContainAndMatchFile("ActionWithAllTypesOfInputs_Untyped.kt")
+            assertSoftly {
+                binding.shouldContainAndMatchFile("ActionWithAllTypesOfInputs.kt")
+                binding.shouldContainAndMatchFile("ActionWithAllTypesOfInputs_Untyped.kt")
+            }
         }
 
         test("action with outputs") {
@@ -471,8 +474,10 @@ class GenerationTest :
                 )
 
             // then
-            binding.shouldContainAndMatchFile("ActionWithPartlyTypings.kt")
-            binding.shouldContainAndMatchFile("ActionWithPartlyTypings_Untyped.kt")
+            assertSoftly {
+                binding.shouldContainAndMatchFile("ActionWithPartlyTypings.kt")
+                binding.shouldContainAndMatchFile("ActionWithPartlyTypings_Untyped.kt")
+            }
         }
     })