diff --git a/json/pickler/src/main/scala/sttp/tapir/json/pickler/CreateDerivedEnumerationPickler.scala b/json/pickler/src/main/scala/sttp/tapir/json/pickler/CreateDerivedEnumerationPickler.scala
index dd015f25ba..d1302c64aa 100644
--- a/json/pickler/src/main/scala/sttp/tapir/json/pickler/CreateDerivedEnumerationPickler.scala
+++ b/json/pickler/src/main/scala/sttp/tapir/json/pickler/CreateDerivedEnumerationPickler.scala
@@ -39,14 +39,14 @@ class CreateDerivedEnumerationPickler[T: ClassTag](
     val tapirPickle = new TapirPickle[T] {
       override lazy val reader: Reader[T] = {
         val readersForPossibleValues: Seq[TaggedReader[T]] =
-          validator.possibleValues.zip(childReadWriters.map(_._1)).map { case (enumValue, reader) =>
-            TaggedReader.Leaf[T](encode(enumValue).toString, reader.asInstanceOf[LeafWrapper[_]].r.asInstanceOf[Reader[T]])
+          childReadWriters.map { case (enumValue, reader, _) =>
+            TaggedReader.Leaf[T](encode(enumValue.asInstanceOf[T]).toString, reader.asInstanceOf[LeafWrapper[_]].r.asInstanceOf[Reader[T]])
           }
         new TaggedReader.Node[T](readersForPossibleValues: _*)
       }
 
       override lazy val writer: Writer[T] =
-        new TaggedWriter.Node[T](childReadWriters.map(_._2.asInstanceOf[TaggedWriter[T]]): _*) {
+        new TaggedWriter.Node[T](childReadWriters.map(_._3.asInstanceOf[TaggedWriter[T]]): _*) {
           override def findWriterWithKey(v: Any): (String, String, ObjectWriter[T]) =
             val (tagKey, tagValue, writer) = super.findWriterWithKey(v)
             // Here our custom encoding transforms the value of a singleton object
@@ -57,15 +57,17 @@ class CreateDerivedEnumerationPickler[T: ClassTag](
     new Pickler[T](tapirPickle, schema)
   }
 
-  private inline def buildEnumerationReadWriters[T: ClassTag, Cases <: Tuple]: List[(Types#Reader[_], Types#Writer[_])] =
+  private inline def buildEnumerationReadWriters[T: ClassTag, Cases <: Tuple]: List[(Any, Types#Reader[_], Types#Writer[_])] =
     inline erasedValue[Cases] match {
       case _: (enumerationCase *: enumerationCasesTail) =>
-        val processedHead = readWriterForEnumerationCase[enumerationCase]
+        val (reader, writer) = readWriterForEnumerationCase[enumerationCase]
         val processedTail = buildEnumerationReadWriters[T, enumerationCasesTail]
-        (processedHead +: processedTail)
+        ((productValue[enumerationCase], reader, writer) +: processedTail)
       case _: EmptyTuple.type => Nil
     }
 
+  private inline def productValue[E] = summonFrom { case m: Mirror.ProductOf[E] => m.fromProduct(EmptyTuple) }
+
   /** Enumeration cases and case objects in an enumeration need special writers and readers, which are generated here, instead of being
     * taken from child picklers. For example, for enum Color and case values Red and Blue, a Writer should just use the object Red or Blue
     * and serialize it to "Red" or "Blue". If user needs to encode the singleton object using a custom function, this happens on a higher
diff --git a/json/pickler/src/test/scala/sttp/tapir/json/pickler/Fixtures.scala b/json/pickler/src/test/scala/sttp/tapir/json/pickler/Fixtures.scala
index 5878fe2622..167de23212 100644
--- a/json/pickler/src/test/scala/sttp/tapir/json/pickler/Fixtures.scala
+++ b/json/pickler/src/test/scala/sttp/tapir/json/pickler/Fixtures.scala
@@ -90,3 +90,7 @@ object Fixtures:
   sealed trait NotAllSealedVariant
   case object NotAllSealedVariantA extends NotAllSealedVariant
   case class NotAllSealedVariantB(innerField: Int) extends NotAllSealedVariant
+
+  enum NotAlphabetical:
+    case Xyz
+    case Fgh
diff --git a/json/pickler/src/test/scala/sttp/tapir/json/pickler/PicklerEnumTest.scala b/json/pickler/src/test/scala/sttp/tapir/json/pickler/PicklerEnumTest.scala
index 0ebf26ce5d..ac3ef40c17 100644
--- a/json/pickler/src/test/scala/sttp/tapir/json/pickler/PicklerEnumTest.scala
+++ b/json/pickler/src/test/scala/sttp/tapir/json/pickler/PicklerEnumTest.scala
@@ -107,4 +107,18 @@ class PicklerEnumTest extends AnyFlatSpec with Matchers {
           18 -> picklerMagenta
         )""")
   }
+
+  it should "encode and decode an enum where the cases are not alphabetically sorted" in {
+    // given
+    import generic.auto.* // for Pickler auto-derivation
+
+    // when
+    val testPickler = Pickler.derived[NotAlphabetical]
+    val codec = testPickler.toCodec
+    val encoded = codec.encode(NotAlphabetical.Xyz)
+
+    // then
+    encoded shouldBe """"Xyz""""
+    codec.decode(encoded) shouldBe Value(NotAlphabetical.Xyz)
+  }
 }