diff --git a/lionweb/src/main/kotlin/com/strumenta/kolasu/lionweb/LionWebModelConverter.kt b/lionweb/src/main/kotlin/com/strumenta/kolasu/lionweb/LionWebModelConverter.kt
index 92dbbce9..35649f64 100644
--- a/lionweb/src/main/kotlin/com/strumenta/kolasu/lionweb/LionWebModelConverter.kt
+++ b/lionweb/src/main/kotlin/com/strumenta/kolasu/lionweb/LionWebModelConverter.kt
@@ -247,6 +247,10 @@ class LionWebModelConverter(
                                             setOriginalNode(lwNode, targetID)
                                         }
                                         setPlaceholderNodeType(instance, origin.javaClass.kotlin)
+                                        instance.setPropertyValue(
+                                            StarLasuLWLanguage.PlaceholderNodeMessageProperty,
+                                            origin.message
+                                        )
                                         lwNode.addAnnotation(instance)
                                     } else {
                                         throw Exception(
@@ -399,7 +403,7 @@ class LionWebModelConverter(
                 throw RuntimeException("Issue instantiating $kClass from LionWeb node $lwNode", e)
             }
         }
-        val placeholderNodes = mutableListOf<KNode>()
+        val placeholderNodes = mutableMapOf<KNode, (KNode) -> Unit>()
         lwTree.thisAndAllDescendants().forEach { lwNode ->
             val kNode = nodesMapping.byB(lwNode)!!
             if (kNode is KNode) {
@@ -419,7 +423,34 @@ class LionWebModelConverter(
                     it.classifier == StarLasuLWLanguage.PlaceholderNode
                 }
                 if (placeholderNodeAnnotation != null) {
-                    placeholderNodes.add(kNode)
+                    val placeholderType = (
+                        placeholderNodeAnnotation.getPropertyValue(
+                            StarLasuLWLanguage.PlaceholderNodeTypeProperty
+                        ) as EnumerationValue
+                        ).enumerationLiteral
+                    val placeholderMessage = placeholderNodeAnnotation.getPropertyValue(
+                        StarLasuLWLanguage.PlaceholderNodeMessageProperty
+                    ) as String
+                    when (placeholderType.name) {
+                        "MissingASTTransformation" -> {
+                            placeholderNodes[kNode] = { kNode ->
+                                kNode.origin = MissingASTTransformation(
+                                    origin = kNode.origin,
+                                    transformationSource = kNode.origin as? KNode,
+                                    expectedType = null
+                                )
+                            }
+                        }
+                        "FailingASTTransformation" -> {
+                            placeholderNodes[kNode] = { kNode ->
+                                kNode.origin = FailingASTTransformation(
+                                    origin = kNode.origin,
+                                    message = placeholderMessage
+                                )
+                            }
+                        }
+                        else -> TODO()
+                    }
                 }
                 val transpiledNodes = lwNode.getReferenceValues(StarLasuLWLanguage.ASTNodeTranspiledNodes)
                 if (transpiledNodes.isNotEmpty()) {
@@ -429,12 +460,10 @@ class LionWebModelConverter(
             }
         }
         referencesPostponer.populateReferences(nodesMapping, externalNodeResolver)
-        placeholderNodes.forEach {
-            it.origin = MissingASTTransformation(
-                origin = it.origin,
-                transformationSource = it.origin as com.strumenta.kolasu.model.Node,
-                expectedType = null
-            )
+        // We want to handle the origin for placeholder nodes AFTER references, to override the origins
+        // set during the population of references
+        placeholderNodes.entries.forEach { entry ->
+            entry.value.invoke(entry.key)
         }
         return nodesMapping.byB(lwTree)!!
     }
diff --git a/lionweb/src/main/kotlin/com/strumenta/kolasu/lionweb/StarLasuLWLanguage.kt b/lionweb/src/main/kotlin/com/strumenta/kolasu/lionweb/StarLasuLWLanguage.kt
index 30dbfcd5..1bf09be4 100644
--- a/lionweb/src/main/kotlin/com/strumenta/kolasu/lionweb/StarLasuLWLanguage.kt
+++ b/lionweb/src/main/kotlin/com/strumenta/kolasu/lionweb/StarLasuLWLanguage.kt
@@ -144,6 +144,14 @@ object StarLasuLWLanguage : Language("com.strumenta.StarLasu") {
             this.setOptional(false)
         }
         placeholderNodeAnnotation.addFeature(type)
+        val message = Property().apply {
+            this.name = "message"
+            this.id = "${placeholderNodeAnnotation.id!!.removeSuffix("-id")}-$name-id"
+            this.key = "${placeholderNodeAnnotation.key!!.removeSuffix("-key")}-$name-key"
+            this.type = LionCoreBuiltins.getString()
+            this.setOptional(false)
+        }
+        placeholderNodeAnnotation.addFeature(message)
         addElement(placeholderNodeAnnotation)
     }
 
@@ -177,6 +185,9 @@ object StarLasuLWLanguage : Language("com.strumenta.StarLasu") {
     val PlaceholderNodeTypeProperty: Property
         get() = PlaceholderNode.getPropertyByName("type")!!
 
+    val PlaceholderNodeMessageProperty: Property
+        get() = PlaceholderNode.getPropertyByName("message")!!
+
     val PlaceholderNodeType: Enumeration
         get() = StarLasuLWLanguage.getEnumerationByName("PlaceholderNodeType")!!
 
diff --git a/lionweb/src/test/kotlin/com/strumenta/kolasu/lionweb/LionWebModelConverterTest.kt b/lionweb/src/test/kotlin/com/strumenta/kolasu/lionweb/LionWebModelConverterTest.kt
index 1633b4cb..addb6250 100644
--- a/lionweb/src/test/kotlin/com/strumenta/kolasu/lionweb/LionWebModelConverterTest.kt
+++ b/lionweb/src/test/kotlin/com/strumenta/kolasu/lionweb/LionWebModelConverterTest.kt
@@ -17,7 +17,9 @@ import com.strumenta.kolasu.parsing.KolasuToken
 import com.strumenta.kolasu.parsing.ParsingResult
 import com.strumenta.kolasu.parsing.TokenCategory
 import com.strumenta.kolasu.testing.assertASTsAreEqual
+import com.strumenta.kolasu.transformation.FailingASTTransformation
 import com.strumenta.kolasu.transformation.MissingASTTransformation
+import com.strumenta.kolasu.transformation.dummyInstance
 import com.strumenta.kolasu.validation.Issue
 import com.strumenta.kolasu.validation.IssueSeverity
 import com.strumenta.kolasu.validation.IssueType
@@ -974,6 +976,51 @@ class LionWebModelConverterTest {
             reimported.tokens.map { it.position }
         )
     }
+
+    @Test
+    fun serializeAndDeserializeNodeWithMissingTransformation() {
+        val myOriginalSource = LionWebSource("Some_dummy_original_source")
+        val myMigratedSource = LionWebSource("Some_dummy_migrated_source")
+        val myOriginalNode = NodeWithEnum::class.dummyInstance()
+        val myTransformedNode = NodeWithEnum::class.dummyInstance()
+        myOriginalNode.source = myOriginalSource
+        myTransformedNode.source = myMigratedSource
+        myTransformedNode.origin = MissingASTTransformation(myOriginalNode)
+
+        val converter = LionWebModelConverter()
+        converter.exportLanguageToLionWeb(
+            KolasuLanguage("myLanguage").apply {
+                addClass(NodeWithEnum::class)
+            }
+        )
+        converter.exportModelToLionWeb(myOriginalNode)
+        val lwNode = converter.exportModelToLionWeb(myTransformedNode)
+        val reimportedNode = converter.importModelFromLionWeb(lwNode) as Node
+        assert(reimportedNode.origin is MissingASTTransformation)
+    }
+
+    @Test
+    fun serializeAndDeserializeNodeWithFailingTransformation() {
+        val myOriginalSource = LionWebSource("Some_dummy_original_source")
+        val myMigratedSource = LionWebSource("Some_dummy_migrated_source")
+        val myOriginalNode = NodeWithEnum::class.dummyInstance()
+        val myTransformedNode = NodeWithEnum::class.dummyInstance()
+        myOriginalNode.source = myOriginalSource
+        myTransformedNode.source = myMigratedSource
+        myTransformedNode.origin = FailingASTTransformation(myOriginalNode, "failing because...")
+
+        val converter = LionWebModelConverter()
+        converter.exportLanguageToLionWeb(
+            KolasuLanguage("myLanguage").apply {
+                addClass(NodeWithEnum::class)
+            }
+        )
+        converter.exportModelToLionWeb(myOriginalNode)
+        val lwNode = converter.exportModelToLionWeb(myTransformedNode)
+        val reimportedNode = converter.importModelFromLionWeb(lwNode) as Node
+        assert(reimportedNode.origin is FailingASTTransformation)
+        assertEquals("failing because...", (reimportedNode.origin as FailingASTTransformation).message)
+    }
 }
 
 @ASTRoot(canBeNotRoot = true)