diff --git a/compiler/src/dotty/tools/dotc/core/TypeErasure.scala b/compiler/src/dotty/tools/dotc/core/TypeErasure.scala
index 0474aff4087a..48fb1bab2da1 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeErasure.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeErasure.scala
@@ -751,12 +751,12 @@ class TypeErasure(sourceLanguage: SourceLanguage, semiEraseVCs: Boolean, isConst
   private def checkedSuperType(tp: TypeProxy)(using Context): Type =
     val tp1 = tp.translucentSuperType
     if !tp1.exists then
-      val msg = tp.typeConstructor match
+      val typeErr = tp.typeConstructor match
         case tycon: TypeRef =>
-          MissingType(tycon.prefix, tycon.name).toMessage.message
+          MissingType(tycon.prefix, tycon.name)
         case _ =>
-          i"Cannot resolve reference to $tp"
-      throw FatalError(msg)
+          TypeError(em"Cannot resolve reference to $tp")
+      throw typeErr
     tp1
 
   /** Widen term ref, skipping any `()` parameter of an eventual getter. Used to erase a TermRef.
diff --git a/compiler/src/dotty/tools/dotc/core/TypeErrors.scala b/compiler/src/dotty/tools/dotc/core/TypeErrors.scala
index 240bc4eebd84..13fe02b712bc 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeErrors.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeErrors.scala
@@ -46,7 +46,8 @@ abstract class TypeError(using creationContext: Context) extends Exception(""):
   def toMessage(using Context): Message
 
   /** Uses creationContext to produce the message */
-  override def getMessage: String = toMessage.message
+  override def getMessage: String =
+    try toMessage.message catch case ex: Throwable => "TypeError"
 
 object TypeError:
   def apply(msg: Message)(using Context) = new TypeError:
diff --git a/compiler/src/dotty/tools/dotc/transform/TreeChecker.scala b/compiler/src/dotty/tools/dotc/transform/TreeChecker.scala
index f1f703fb07ee..0515a6978a47 100644
--- a/compiler/src/dotty/tools/dotc/transform/TreeChecker.scala
+++ b/compiler/src/dotty/tools/dotc/transform/TreeChecker.scala
@@ -418,31 +418,35 @@ object TreeChecker {
     }
 
     override def typedUnadapted(tree: untpd.Tree, pt: Type, locked: TypeVars)(using Context): Tree = {
-      val res = tree match {
-        case _: untpd.TypedSplice | _: untpd.Thicket | _: EmptyValDef[?] =>
-          super.typedUnadapted(tree, pt, locked)
-        case _ if tree.isType =>
-          promote(tree)
-        case _ =>
-          val tree1 = super.typedUnadapted(tree, pt, locked)
-          def isSubType(tp1: Type, tp2: Type) =
-            (tp1 eq tp2) || // accept NoType / NoType
-            (tp1 <:< tp2)
-          def divergenceMsg(tp1: Type, tp2: Type) =
-            s"""Types differ
-               |Original type : ${tree.typeOpt.show}
-               |After checking: ${tree1.tpe.show}
-               |Original tree : ${tree.show}
-               |After checking: ${tree1.show}
-               |Why different :
-             """.stripMargin + core.TypeComparer.explained(_.isSubType(tp1, tp2))
-          if (tree.hasType) // it might not be typed because Typer sometimes constructs new untyped trees and resubmits them to typedUnadapted
-            assert(isSubType(tree1.tpe, tree.typeOpt), divergenceMsg(tree1.tpe, tree.typeOpt))
-          tree1
-      }
-      checkNoOrphans(res.tpe)
-      phasesToCheck.foreach(_.checkPostCondition(res))
-      res
+      try
+        val res = tree match
+          case _: untpd.TypedSplice | _: untpd.Thicket | _: EmptyValDef[?] =>
+            super.typedUnadapted(tree, pt, locked)
+          case _ if tree.isType =>
+            promote(tree)
+          case _ =>
+            val tree1 = super.typedUnadapted(tree, pt, locked)
+            def isSubType(tp1: Type, tp2: Type) =
+              (tp1 eq tp2) || // accept NoType / NoType
+              (tp1 <:< tp2)
+            def divergenceMsg(tp1: Type, tp2: Type) =
+              s"""Types differ
+                |Original type : ${tree.typeOpt.show}
+                |After checking: ${tree1.tpe.show}
+                |Original tree : ${tree.show}
+                |After checking: ${tree1.show}
+                |Why different :
+              """.stripMargin + core.TypeComparer.explained(_.isSubType(tp1, tp2))
+            if (tree.hasType) // it might not be typed because Typer sometimes constructs new untyped trees and resubmits them to typedUnadapted
+              assert(isSubType(tree1.tpe, tree.typeOpt), divergenceMsg(tree1.tpe, tree.typeOpt))
+            tree1
+        checkNoOrphans(res.tpe)
+        phasesToCheck.foreach(_.checkPostCondition(res))
+        res
+      catch case NonFatal(ex) if !ctx.run.enrichedErrorMessage =>
+        val treeStr = tree.show(using ctx.withPhase(ctx.phase.prev.megaPhase))
+        println(ctx.run.enrichErrorMessage(s"exception while retyping $treeStr of class ${tree.className} # ${tree.uniqueId}"))
+        throw ex
     }
 
     def checkNotRepeated(tree: Tree)(using Context): tree.type = {
diff --git a/compiler/src/dotty/tools/dotc/typer/ReTyper.scala b/compiler/src/dotty/tools/dotc/typer/ReTyper.scala
index e152b5e6b9c7..9741a366da89 100644
--- a/compiler/src/dotty/tools/dotc/typer/ReTyper.scala
+++ b/compiler/src/dotty/tools/dotc/typer/ReTyper.scala
@@ -170,13 +170,6 @@ class ReTyper(nestingLevel: Int = 0) extends Typer(nestingLevel) with ReChecking
   override def addCanThrowCapabilities(expr: untpd.Tree, cases: List[CaseDef])(using Context): untpd.Tree =
     expr
 
-  override def typedUnadapted(tree: untpd.Tree, pt: Type, locked: TypeVars)(using Context): Tree =
-    try super.typedUnadapted(tree, pt, locked)
-    catch case NonFatal(ex) if ctx.phase != Phases.typerPhase && ctx.phase != Phases.inliningPhase && !ctx.run.enrichedErrorMessage =>
-      val treeStr = tree.show(using ctx.withPhase(ctx.phase.prev.megaPhase))
-      println(ctx.run.enrichErrorMessage(s"exception while retyping $treeStr of class ${tree.className} # ${tree.uniqueId}"))
-      throw ex
-
   override def inlineExpansion(mdef: DefDef)(using Context): List[Tree] = mdef :: Nil
 
   override def inferView(from: Tree, to: Type)(using Context): Implicits.SearchResult =
diff --git a/tests/pos/i19929.scala b/tests/pos/i19929.scala
new file mode 100644
index 000000000000..2e1c691af8f5
--- /dev/null
+++ b/tests/pos/i19929.scala
@@ -0,0 +1,5 @@
+trait A:
+  private type M
+
+def foo(a: A{type M = Int}) =
+  val _: a.M = ??? // was crash