diff --git a/compiler/src/dotty/tools/dotc/reporting/ErrorMessageID.scala b/compiler/src/dotty/tools/dotc/reporting/ErrorMessageID.scala
index ff0aac879752..c3cad8cbfea5 100644
--- a/compiler/src/dotty/tools/dotc/reporting/ErrorMessageID.scala
+++ b/compiler/src/dotty/tools/dotc/reporting/ErrorMessageID.scala
@@ -216,6 +216,10 @@ enum ErrorMessageID(val isActive: Boolean = true) extends java.lang.Enum[ErrorMe
   case FinalLocalDefID // errorNumber: 200
   case NonNamedArgumentInJavaAnnotationID // errorNumber: 201 - unused in LTS
   case QuotedTypeMissingID // errorNumber: 202
+  case DeprecatedAssignmentSyntaxID // errorNumber: 203
+  case DeprecatedInfixNamedArgumentSyntaxID // errorNumber: 204
+  case GivenSearchPriorityID // errorNumber: 205
+  case EnumMayNotBeValueClassesID // errorNumber: 206
 
   def errorNumber = ordinal - 1
 
diff --git a/compiler/src/dotty/tools/dotc/reporting/messages.scala b/compiler/src/dotty/tools/dotc/reporting/messages.scala
index de59c21896b6..8acf237e8e7c 100644
--- a/compiler/src/dotty/tools/dotc/reporting/messages.scala
+++ b/compiler/src/dotty/tools/dotc/reporting/messages.scala
@@ -1812,12 +1812,12 @@ class NotAPath(tp: Type, usage: String)(using Context) extends TypeMsg(NotAPathI
     if sym.isAllOf(Flags.InlineParam) then
       i"""
          |Inline parameters are not considered immutable paths and cannot be used as
-         |singleton types. 
-         | 
+         |singleton types.
+         |
          |Hint: Removing the `inline` qualifier from the `${sym.name}` parameter
          |may help resolve this issue."""
     else ""
-    
+
 
 class WrongNumberOfParameters(tree: untpd.Tree, foundCount: Int, pt: Type, expectedCount: Int)(using Context)
   extends SyntaxMsg(WrongNumberOfParametersID) {
@@ -3173,15 +3173,21 @@ final class QuotedTypeMissing(tpe: Type)(using Context) extends StagingMessage(Q
 
   private def witness = defn.QuotedTypeClass.typeRef.appliedTo(tpe)
 
-  override protected def msg(using Context): String = 
+  override protected def msg(using Context): String =
     i"Reference to $tpe within quotes requires a given ${witness} in scope"
 
   override protected def explain(using Context): String =
-    i"""Referencing `$tpe` inside a quoted expression requires a `${witness}` to be in scope. 
+    i"""Referencing `$tpe` inside a quoted expression requires a `${witness}` to be in scope.
         |Since Scala is subject to erasure at runtime, the type information will be missing during the execution of the code.
-        |`${witness}` is therefore needed to carry `$tpe`'s type information into the quoted code. 
-        |Without an implicit `${witness}`, the type `$tpe` cannot be properly referenced within the expression. 
+        |`${witness}` is therefore needed to carry `$tpe`'s type information into the quoted code.
+        |Without an implicit `${witness}`, the type `$tpe` cannot be properly referenced within the expression.
         |To resolve this, ensure that a `${witness}` is available, either through a context-bound or explicitly.
         |"""
 
 end QuotedTypeMissing
+
+final class EnumMayNotBeValueClasses(sym: Symbol)(using Context) extends SyntaxMsg(EnumMayNotBeValueClassesID):
+    def msg(using Context): String = i"$sym may not be a value class"
+
+    def explain(using Context) = ""
+end EnumMayNotBeValueClasses
diff --git a/compiler/src/dotty/tools/dotc/typer/Checking.scala b/compiler/src/dotty/tools/dotc/typer/Checking.scala
index cd00ca9340c6..bf99def353b0 100644
--- a/compiler/src/dotty/tools/dotc/typer/Checking.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Checking.scala
@@ -715,11 +715,16 @@ object Checking {
       case _ =>
         report.error(ValueClassesMayNotContainInitalization(clazz), stat.srcPos)
     }
-    if (clazz.isDerivedValueClass) {
+    // We don't check synthesised enum anonymous classes that are generated from
+    // enum extending a value class type (AnyVal or an alias of it)
+    // The error message 'EnumMayNotBeValueClassesID' will take care of generating the error message (See #22236)
+    if (clazz.isDerivedValueClass && !clazz.isEnumAnonymClass) {
       if (clazz.is(Trait))
         report.error(CannotExtendAnyVal(clazz), clazz.srcPos)
       if clazz.is(Module) then
         report.error(CannotExtendAnyVal(clazz), clazz.srcPos)
+      if (clazz.is(Enum))
+        report.error(EnumMayNotBeValueClasses(clazz), clazz.srcPos)
       if (clazz.is(Abstract))
         report.error(ValueClassesMayNotBeAbstract(clazz), clazz.srcPos)
       if (!clazz.isStatic)
diff --git a/compiler/src/dotty/tools/dotc/typer/Namer.scala b/compiler/src/dotty/tools/dotc/typer/Namer.scala
index c1a6861102fb..d98790b89600 100644
--- a/compiler/src/dotty/tools/dotc/typer/Namer.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Namer.scala
@@ -1581,7 +1581,8 @@ class Namer { typer: Typer =>
           }
           else {
             val pclazz = pt.typeSymbol
-            if pclazz.is(Final) then
+            // The second condition avoids generating a useless message (See #22236 for more details)
+            if pclazz.is(Final) && !(pclazz.is(Enum) && pclazz.isDerivedValueClass) then
               report.error(ExtendFinalClass(cls, pclazz), cls.srcPos)
             else if pclazz.isEffectivelySealed && pclazz.associatedFile != cls.associatedFile then
               if pclazz.is(Sealed) && !pclazz.is(JavaDefined) then
diff --git a/tests/neg/i21944.check b/tests/neg/i21944.check
new file mode 100644
index 000000000000..591447c6a510
--- /dev/null
+++ b/tests/neg/i21944.check
@@ -0,0 +1,4 @@
+-- [E206] Syntax Error: tests/neg/i21944.scala:1:5 ---------------------------------------------------------------------
+1 |enum Orientation extends AnyVal: // error
+  |     ^
+  |     class Orientation may not be a value class
diff --git a/tests/neg/i21944.scala b/tests/neg/i21944.scala
new file mode 100644
index 000000000000..bf335e56c671
--- /dev/null
+++ b/tests/neg/i21944.scala
@@ -0,0 +1,2 @@
+enum Orientation extends AnyVal: // error
+    case North, South, East, West