diff --git a/core/src/main/scala-2/sttp/tapir/macros/LowPrioSchemaMacrosVersionSpecific.scala b/core/src/main/scala-2/sttp/tapir/macros/LowPrioSchemaMacrosVersionSpecific.scala
deleted file mode 100644
index 7c77e3bbc2..0000000000
--- a/core/src/main/scala-2/sttp/tapir/macros/LowPrioSchemaMacrosVersionSpecific.scala
+++ /dev/null
@@ -1,4 +0,0 @@
-package sttp.tapir
-package macros
-
-trait LowPrioSchemaMacrosVersionSpecific
diff --git a/core/src/main/scala-2/sttp/tapir/macros/SchemaCompanionMacrosExtensions.scala b/core/src/main/scala-2/sttp/tapir/macros/SchemaCompanionMacrosExtensions.scala
new file mode 100644
index 0000000000..a302d1a4be
--- /dev/null
+++ b/core/src/main/scala-2/sttp/tapir/macros/SchemaCompanionMacrosExtensions.scala
@@ -0,0 +1,4 @@
+package sttp.tapir
+package macros
+
+trait SchemaCompanionMacrosExtensions
diff --git a/core/src/main/scala-3/sttp/tapir/macros/CodecMacros.scala b/core/src/main/scala-3/sttp/tapir/macros/CodecMacros.scala
index c63d9dac46..45b50d5c7c 100644
--- a/core/src/main/scala-3/sttp/tapir/macros/CodecMacros.scala
+++ b/core/src/main/scala-3/sttp/tapir/macros/CodecMacros.scala
@@ -3,6 +3,10 @@ package sttp.tapir.macros
 import sttp.tapir.CodecFormat.TextPlain
 import sttp.tapir.{Codec, SchemaAnnotations, Validator}
 import sttp.tapir.internal.CodecValueClassMacro
+import sttp.tapir.Mapping
+import sttp.tapir.DecodeResult
+import sttp.tapir.DecodeResult.Value
+import sttp.tapir.Schema
 
 trait CodecMacros {
 
@@ -36,6 +40,11 @@ trait CodecMacros {
   inline def derivedEnumerationValueCustomise[L, T <: scala.Enumeration#Value]: CreateDerivedEnumerationCodec[L, T] =
     new CreateDerivedEnumerationCodec(derivedEnumerationValueValidator[T], SchemaAnnotations.derived[T])
 
+  inline given derivedStringBasedUnionEnumeration[T](using IsUnionOf[String, T]): Codec[String, T, TextPlain] =
+    lazy val values = UnionDerivation.constValueUnionTuple[String, T]
+    lazy val validator = Validator.enumeration(values.toList.asInstanceOf[List[T]])
+    Codec.string.validate(validator.asInstanceOf[Validator[String]]).map(_.asInstanceOf[T])(_.asInstanceOf[String])
+
   /** A default codec for enumerations, which returns a string-based enumeration codec, using the enum's `.toString` to encode values, and
     * performing a case-insensitive search through the possible values, converted to strings using `.toString`.
     *
diff --git a/core/src/main/scala-3/sttp/tapir/macros/LowPrioSchemaMacrosVersionSpecific.scala b/core/src/main/scala-3/sttp/tapir/macros/LowPrioSchemaMacrosVersionSpecific.scala
deleted file mode 100644
index c0634480fd..0000000000
--- a/core/src/main/scala-3/sttp/tapir/macros/LowPrioSchemaMacrosVersionSpecific.scala
+++ /dev/null
@@ -1,21 +0,0 @@
-package sttp.tapir
-package macros
-
-import sttp.tapir.Schema.SName
-
-import scala.compiletime.*
-import scala.compiletime.ops.any.IsConst
-
-trait LowPrioSchemaMacrosVersionSpecific:
-  inline given derivedStringBasedUnionEnumeration[S](using IsUnionOf[String, S]): Schema[S] =
-    val values = UnionDerivation.constValueUnionTuple[String, S]
-    Schema
-      .string[S]
-      .name(SName(values.toList.mkString("_or_")))
-      .validate(Validator.enumeration(values.toList.asInstanceOf[List[S]]))
-
-  inline given constStringToEnum[S <: String](using IsConst[S] =:= true): Schema[S] =
-    Schema
-      .string[S]
-      .name(SName(constValue[S]))
-      .validate(Validator.enumeration(List(constValue[S]).asInstanceOf[List[S]]))
diff --git a/core/src/main/scala-3/sttp/tapir/macros/SchemaCompanionMacrosExtensions.scala b/core/src/main/scala-3/sttp/tapir/macros/SchemaCompanionMacrosExtensions.scala
new file mode 100644
index 0000000000..2e71be73e6
--- /dev/null
+++ b/core/src/main/scala-3/sttp/tapir/macros/SchemaCompanionMacrosExtensions.scala
@@ -0,0 +1,15 @@
+package sttp.tapir
+package macros
+
+import sttp.tapir.Schema.SName
+
+object SchemaCompanionMacrosExtensions extends SchemaCompanionMacrosExtensions
+
+trait SchemaCompanionMacrosExtensions:
+  inline given derivedStringBasedUnionEnumeration[S](using IsUnionOf[String, S]): Schema[S] =
+    lazy val values = UnionDerivation.constValueUnionTuple[String, S]
+    lazy val validator = Validator.enumeration(values.toList.asInstanceOf[List[S]])
+    Schema
+      .string[S]
+      .name(SName(values.toList.mkString("_or_")))
+      .validate(validator)
diff --git a/core/src/main/scala-3/sttp/tapir/macros/union_derivation.scala b/core/src/main/scala-3/sttp/tapir/macros/union_derivation.scala
index 2bd64a3129..47e9c46124 100644
--- a/core/src/main/scala-3/sttp/tapir/macros/union_derivation.scala
+++ b/core/src/main/scala-3/sttp/tapir/macros/union_derivation.scala
@@ -5,9 +5,9 @@ import scala.deriving.*
 import scala.quoted.*
 
 @scala.annotation.implicitNotFound("${A} is not a union of ${T}")
-sealed trait IsUnionOf[T, A]
+private[tapir] sealed trait IsUnionOf[T, A]
 
-object IsUnionOf:
+private[tapir] object IsUnionOf:
 
   private val singleton: IsUnionOf[Any, Any] = new IsUnionOf[Any, Any] {}
 
@@ -31,9 +31,11 @@ object IsUnionOf:
       case o: OrType =>
         validateTypes(o)
         ('{ IsUnionOf.singleton.asInstanceOf[IsUnionOf[T, A]] }).asExprOf[IsUnionOf[T, A]]
-      case other => report.errorAndAbort(s"${tpe.show} is not a Union")
+      case o =>
+        if o <:< bound then ('{ IsUnionOf.singleton.asInstanceOf[IsUnionOf[T, A]] }).asExprOf[IsUnionOf[T, A]]
+        else report.errorAndAbort(s"${tpe.show} is not a Union")
 
-object UnionDerivation:
+private[tapir] object UnionDerivation:
   transparent inline def constValueUnionTuple[T, A](using IsUnionOf[T, A]): Tuple = ${ constValueUnionTupleImpl[T, A] }
 
   private def constValueUnionTupleImpl[T: Type, A: Type](using Quotes): Expr[Tuple] =
diff --git a/core/src/main/scala/sttp/tapir/Schema.scala b/core/src/main/scala/sttp/tapir/Schema.scala
index 9844d360a1..1826df96c8 100644
--- a/core/src/main/scala/sttp/tapir/Schema.scala
+++ b/core/src/main/scala/sttp/tapir/Schema.scala
@@ -5,7 +5,7 @@ import sttp.tapir.Schema.{SName, Title}
 import sttp.tapir.SchemaType._
 import sttp.tapir.generic.{Configuration, Derived}
 import sttp.tapir.internal.{ValidatorSyntax, isBasicValue}
-import sttp.tapir.macros.{LowPrioSchemaMacrosVersionSpecific, SchemaCompanionMacros, SchemaMacros}
+import sttp.tapir.macros.{SchemaCompanionMacrosExtensions, SchemaCompanionMacros, SchemaMacros}
 import sttp.tapir.model.Delimited
 
 import java.io.InputStream
@@ -422,6 +422,6 @@ object Schema extends LowPrioritySchema with SchemaCompanionMacros {
   def anyObject[T]: Schema[T] = Schema(SProduct(Nil), None)
 }
 
-trait LowPrioritySchema extends LowPrioSchemaMacrosVersionSpecific {
+trait LowPrioritySchema extends SchemaCompanionMacrosExtensions {
   implicit def derivedSchema[T](implicit derived: Derived[Schema[T]]): Schema[T] = derived.value
 }
diff --git a/core/src/test/scala-3/sttp/tapir/CodecScala3Test.scala b/core/src/test/scala-3/sttp/tapir/CodecScala3Test.scala
new file mode 100644
index 0000000000..75ba64a0c2
--- /dev/null
+++ b/core/src/test/scala-3/sttp/tapir/CodecScala3Test.scala
@@ -0,0 +1,25 @@
+package sttp.tapir
+
+import org.scalatest.{Assertion, Inside}
+import org.scalatest.flatspec.AnyFlatSpec
+import org.scalatest.matchers.should.Matchers
+import org.scalatestplus.scalacheck.Checkers
+import sttp.tapir.CodecFormat.TextPlain
+import sttp.tapir.DecodeResult.Value
+
+import sttp.tapir.DecodeResult.InvalidValue
+
+class CodecScala3Test extends AnyFlatSpec with Matchers with Checkers with Inside {
+
+  it should "derive a codec for a string-based union type" in {
+    // given
+    val codec = summon[Codec[String, "Apple" | "Banana", TextPlain]]
+
+    // then
+    codec.encode("Apple") shouldBe "Apple"
+    codec.encode("Banana") shouldBe "Banana"
+    codec.decode("Apple") shouldBe Value("Apple")
+    codec.decode("Banana") shouldBe Value("Banana")
+    codec.decode("Orange") should matchPattern { case DecodeResult.InvalidValue(List(ValidationError(_, "Orange", _, _))) => }
+  }
+}
diff --git a/core/src/test/scala-3/sttp/tapir/SchemaMacroScala3Test.scala b/core/src/test/scala-3/sttp/tapir/SchemaMacroScala3Test.scala
index 66279c178f..968104e971 100644
--- a/core/src/test/scala-3/sttp/tapir/SchemaMacroScala3Test.scala
+++ b/core/src/test/scala-3/sttp/tapir/SchemaMacroScala3Test.scala
@@ -101,7 +101,7 @@ class SchemaMacroScala3Test extends AnyFlatSpec with Matchers:
 
   it should "derive schema for a const as a string-based union type" in {
     // when
-    val s: Schema["a"] = Schema.constStringToEnum
+    val s: Schema["a"] = Schema.derivedStringBasedUnionEnumeration
 
     // then
     s.name.map(_.show) shouldBe Some("a")
@@ -110,6 +110,20 @@ class SchemaMacroScala3Test extends AnyFlatSpec with Matchers:
     s.validator should matchPattern { case Validator.Enumeration(List("a"), _, _) => }
   }
 
+  it should "derive a schema for a union of unions when all are string-based constants" in {
+    // when
+    type AorB = "a" | "b"
+    type C = "c"
+    type AorBorC = AorB | C
+    val s: Schema[AorBorC] = Schema.derivedStringBasedUnionEnumeration[AorBorC]
+
+    // then
+    s.name.map(_.show) shouldBe Some("a_or_b_or_c")
+
+    s.schemaType should matchPattern { case SchemaType.SString() => }
+    s.validator should matchPattern { case Validator.Enumeration(List("a", "b", "c"), _, _) => }
+  }
+
 object SchemaMacroScala3Test:
   enum Fruit:
     case Apple, Banana
diff --git a/doc/endpoint/enumerations.md b/doc/endpoint/enumerations.md
index 8099ae921a..06bf3929a4 100644
--- a/doc/endpoint/enumerations.md
+++ b/doc/endpoint/enumerations.md
@@ -263,6 +263,23 @@ enum ColorEnum {
 given Schema[ColorEnum] = Schema.derivedEnumeration.defaultStringBased
 ```
 
+### Scala 3 string-based constant union types to enum
+
+If a union type is a string-based constant union type, it can be auto-derived as field type or manually derived by using the `Schema.derivedStringBasedUnionEnumeration[T]` method.
+
+Constant strings can be derived by using the `Schema.constStringToEnum[T]` method.
+
+Examples:
+```scala
+val aOrB: Schema["a" | "b"] = Schema.derivedStringBasedUnionEnumeration
+```
+```scala
+val a: Schema["a"] = Schema.constStringToEnum
+```
+```scala
+case class Foo(aOrB: "a" | "b", optA: Option["a"]) derives Schema
+```
+
 ### Creating an enum schema by hand
 
 Creating an enumeration [schema](schema.md) by hand is exactly the same as for any other type. The only difference
diff --git a/doc/endpoint/schemas.md b/doc/endpoint/schemas.md
index 53bd6a85cd..f31804d563 100644
--- a/doc/endpoint/schemas.md
+++ b/doc/endpoint/schemas.md
@@ -118,21 +118,9 @@ If any of the components of the union type is a generic type, any of its validat
 the union type, as it's not possible to generate a runtime check for the generic type.
 
 ### Derivation for string-based constant union types
+e.g. `type AorB = "a" | "b"`
 
-If a union type is a string-based constant union type, it can be auto-derived as field type or manually derived by using the `Schema.derivedStringBasedUnionEnumeration[T]` method.
-
-Constant strings can be derived by using the `Schema.constStringToEnum[T]` method.
-
-Examples:
-```scala
-val aOrB: Schema["a" | "b"] = Schema.derivedStringBasedUnionEnumeration
-```
-```scala
-val a: Schema["a"] = Schema.constStringToEnum
-```
-```scala
-case class Foo(aOrB: "a" | "b", optA: Option["a"]) derives Schema
-```
+See [enumerations](enumerations.md#scala-3-string-based-constant-union-types-to-enum) on how to use string-based unions of constant types as enums.
 
 ## Configuring derivation