diff --git a/ducktape/src/main/scala/io/github/arainko/ducktape/Field.scala b/ducktape/src/main/scala/io/github/arainko/ducktape/Field.scala
index 0e0f23e1..7257c848 100644
--- a/ducktape/src/main/scala/io/github/arainko/ducktape/Field.scala
+++ b/ducktape/src/main/scala/io/github/arainko/ducktape/Field.scala
@@ -26,6 +26,8 @@ object Field {
   @compileTimeOnly("Field.default is only useable as a field configuration for transformations")
   def default[A, B, FieldType](selector: Selector ?=> B => FieldType): Field[A, B] = ???
 
+  def useNones[A, B, FieldType](selector: Selector ?=> B => FieldType): Field[A, B] = ???
+
   @compileTimeOnly("Field.allMatching is only useable as a field configuration for transformations")
   def allMatching[A, B, DestFieldTpe, ProductTpe](selector: Selector ?=> B => DestFieldTpe, product: ProductTpe): Field[A, B] =
     ???
diff --git a/ducktape/src/main/scala/io/github/arainko/ducktape/Playground.scala b/ducktape/src/main/scala/io/github/arainko/ducktape/Playground.scala
new file mode 100644
index 00000000..19690367
--- /dev/null
+++ b/ducktape/src/main/scala/io/github/arainko/ducktape/Playground.scala
@@ -0,0 +1,21 @@
+package io.github.arainko.ducktape
+
+final case class SourceToplevel(level1: SourceLevel1)
+final case class SourceLevel1(str: String)
+
+final case class DestToplevel(extra: Option[Int], level1: DestLevel1)
+final case class DestLevel1(extra: Option[Int], str: String)
+
+object Playground extends App {
+  val source = SourceToplevel(SourceLevel1("str"))
+
+  val dest =
+    source
+      .into[DestToplevel]
+      .transform(
+        Field.const(_.extra, Some(1)),
+        Field.useNones(a => a.level1)
+      )
+
+  println(dest)
+}
diff --git a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Configuration.scala b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Configuration.scala
index d2c0f86b..64100e4b 100644
--- a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Configuration.scala
+++ b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Configuration.scala
@@ -15,12 +15,22 @@ private[ducktape] enum Configuration derives Debug {
 
 private[ducktape] object Configuration {
 
+  trait Modifier {
+    def apply(plan: Plan.Error)(using Quotes): Configuration | plan.type
+  }
+
+  object Modifier {
+    given Debug[Modifier] = new:
+      extension (self: Modifier) def show(using Quotes): String = "Modifier(...)"
+  }
+
   enum At derives Debug {
     def path: Path
     def target: Target
     def span: Span
 
     case Successful(path: Path, target: Target, config: Configuration, span: Span)
+    case Regional(path: Path, target: Target, modifier: Modifier, span: Span)
     case Failed(path: Path, target: Target, message: String, span: Span)
   }
 
@@ -120,6 +130,18 @@ private[ducktape] object Configuration {
             Span.fromPosition(cfg.pos)
           ) :: Nil
 
+        case cfg @ Apply(
+              TypeApply(Select(IdentOfType('[Field.type]), "useNones"), a :: b :: destFieldTpe :: Nil),
+              PathSelector(path) :: Nil
+            ) =>
+          val modifier: Modifier = new:
+            def apply(plan: Plan.Error)(using Quotes): Configuration | plan.type =
+              plan.destTpe match {
+                case tpe @ '[Option[a]] => Configuration.Const('{ None }, tpe)
+                case _                  => plan
+              }
+          Configuration.At.Regional(path, Target.Dest, modifier, Span.fromPosition(cfg.pos)) :: Nil
+
         case DeprecatedConfig(configs) => configs
 
         case oopsie =>
diff --git a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Logger.scala b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Logger.scala
index 019bedb6..469c364c 100644
--- a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Logger.scala
+++ b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Logger.scala
@@ -8,7 +8,7 @@ import scala.quoted.*
 private[ducktape] object Logger {
 
   // Logger Config
-  private[ducktape] transparent inline given level: Level = Level.Off
+  private[ducktape] transparent inline given level: Level = Level.Info
   private val output = Output.StdOut
   private def filter(msg: String, meta: Metainformation) = true
 
diff --git a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Plan.scala b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Plan.scala
index 6899968c..443f153d 100644
--- a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Plan.scala
+++ b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Plan.scala
@@ -6,9 +6,7 @@ import io.github.arainko.ducktape.internal.*
 import scala.collection.immutable.ListMap
 import scala.quoted.*
 
-private[ducktape] type PlanError = Plan.Error
-
-private[ducktape] enum Plan[+E <: PlanError] {
+private[ducktape] sealed trait Plan[+E <: Plan.Error] {
   import Plan.*
 
   def sourceTpe: Type[?]
@@ -22,15 +20,17 @@ private[ducktape] enum Plan[+E <: PlanError] {
   final def configureAll(configs: List[Configuration.At])(using Quotes): Plan.Reconfigured = PlanConfigurer.run(this, configs)
 
   final def refine: Either[NonEmptyList[Plan.Error], Plan[Nothing]] = PlanRefiner.run(this)
+}
 
-  case Upcast(
+private[ducktape] object Plan {
+  case class Upcast(
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
     destContext: Path
   ) extends Plan[Nothing]
 
-  case UserDefined(
+  case class UserDefined(
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
@@ -38,7 +38,7 @@ private[ducktape] enum Plan[+E <: PlanError] {
     transformer: Expr[Transformer[?, ?]]
   ) extends Plan[Nothing]
 
-  case Derived(
+  case class Derived(
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
@@ -46,7 +46,7 @@ private[ducktape] enum Plan[+E <: PlanError] {
     transformer: Expr[Transformer.Derived[?, ?]]
   ) extends Plan[Nothing]
 
-  case Configured(
+  case class Configured(
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
@@ -54,7 +54,7 @@ private[ducktape] enum Plan[+E <: PlanError] {
     config: Configuration
   ) extends Plan[Nothing]
 
-  case BetweenProductFunction(
+  case class BetweenProductFunction[+E <: Plan.Error](
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
@@ -63,14 +63,14 @@ private[ducktape] enum Plan[+E <: PlanError] {
     function: Function
   ) extends Plan[E]
 
-  case BetweenUnwrappedWrapped(
+  case class BetweenUnwrappedWrapped(
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
     destContext: Path
   ) extends Plan[Nothing]
 
-  case BetweenWrappedUnwrapped(
+  case class BetweenWrappedUnwrapped(
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
@@ -78,7 +78,7 @@ private[ducktape] enum Plan[+E <: PlanError] {
     fieldName: String
   ) extends Plan[Nothing]
 
-  case BetweenSingletons(
+  case class BetweenSingletons(
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
@@ -86,7 +86,7 @@ private[ducktape] enum Plan[+E <: PlanError] {
     expr: Expr[Any]
   ) extends Plan[Nothing]
 
-  case BetweenProducts(
+  case class BetweenProducts[+E <: Plan.Error](
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
@@ -94,7 +94,7 @@ private[ducktape] enum Plan[+E <: PlanError] {
     fieldPlans: Map[String, Plan[E]]
   ) extends Plan[E]
 
-  case BetweenCoproducts(
+  case class BetweenCoproducts[+E <: Plan.Error](
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
@@ -102,7 +102,7 @@ private[ducktape] enum Plan[+E <: PlanError] {
     casePlans: Vector[Plan[E]]
   ) extends Plan[E]
 
-  case BetweenOptions(
+  case class BetweenOptions[+E <: Plan.Error](
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
@@ -110,7 +110,7 @@ private[ducktape] enum Plan[+E <: PlanError] {
     plan: Plan[E]
   ) extends Plan[E]
 
-  case BetweenNonOptionOption(
+  case class BetweenNonOptionOption[+E <: Plan.Error](
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
@@ -118,7 +118,7 @@ private[ducktape] enum Plan[+E <: PlanError] {
     plan: Plan[E]
   ) extends Plan[E]
 
-  case BetweenCollections(
+  case class BetweenCollections[+E <: Plan.Error](
     destCollectionTpe: Type[? <: Iterable[?]],
     sourceTpe: Type[?],
     destTpe: Type[?],
@@ -127,7 +127,7 @@ private[ducktape] enum Plan[+E <: PlanError] {
     plan: Plan[E]
   ) extends Plan[E]
 
-  case Error(
+  case class Error(
     sourceTpe: Type[?],
     destTpe: Type[?],
     sourceContext: Path,
@@ -135,9 +135,6 @@ private[ducktape] enum Plan[+E <: PlanError] {
     message: ErrorMessage,
     suppressed: Option[Plan.Error]
   ) extends Plan[Plan.Error]
-}
-
-private[ducktape] object Plan {
 
   object Error {
     def from(plan: Plan[Plan.Error], message: ErrorMessage, suppressed: Option[Plan.Error]): Plan.Error =
diff --git a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/PlanConfigurer.scala b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/PlanConfigurer.scala
index 5af362d9..5aa3b5dd 100644
--- a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/PlanConfigurer.scala
+++ b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/PlanConfigurer.scala
@@ -113,6 +113,9 @@ private[ducktape] object PlanConfigurer {
             )
             .tap(errors.addOne)
 
+      case cfg @ Configuration.At.Regional(path, target, modifier, span) =>
+        regional(current, modifier)
+
       case cfg @ Configuration.At.Failed(path, target, message, span) =>
         Plan.Error.from(current, ErrorMessage.ConfigurationFailed(cfg), None).tap(errors.addOne)
     }
@@ -125,4 +128,51 @@ private[ducktape] object PlanConfigurer {
       case other =>
         Plan.Error.from(plan, ErrorMessage.InvalidPathSegment(segment, config.target, config.span), None)
     }
+
+  def regional(
+    plan: Plan[Plan.Error],
+    modifier: Configuration.Modifier
+  )(using Quotes): Plan[Plan.Error] =
+    plan match {
+      case plan: Upcast => plan
+
+      case plan: UserDefined => plan
+
+      case plan: Derived => plan
+
+      case plan: Configured => plan
+
+      case plan: BetweenProductFunction[Plan.Error] =>
+        plan.copy(argPlans = plan.argPlans.transform((_, plan) => regional(plan, modifier)))
+
+      case plan: BetweenUnwrappedWrapped => plan
+
+      case plan: BetweenWrappedUnwrapped => plan
+
+      case plan: BetweenSingletons => plan
+
+      case plan: BetweenProducts[Plan.Error] =>
+        plan.copy(fieldPlans = plan.fieldPlans.transform((_, plan) => regional(plan, modifier)))
+
+      case plan: BetweenCoproducts[Plan.Error] =>
+        plan.copy(casePlans = plan.casePlans.map(regional(_, modifier)))
+
+      case plan: BetweenOptions[Plan.Error] =>
+        plan.copy(plan = regional(plan.plan, modifier))
+
+      case plan: BetweenNonOptionOption[Plan.Error] =>
+        plan.copy(plan = regional(plan.plan, modifier))
+
+      case plan: BetweenCollections[Plan.Error] =>
+        plan.copy(plan = regional(plan.plan, modifier))
+
+      case plan: Error => 
+        modifier(plan) match {
+          case config: Configuration =>
+            Plan.Configured(plan.sourceTpe, plan.destTpe, plan.sourceContext, plan.destContext, config)
+          case other: plan.type => 
+            other
+        }
+    }
+
 }
diff --git a/tooling/src/main/scala/io/github/arainko/tooling/Debug.scala b/tooling/src/main/scala/io/github/arainko/tooling/Debug.scala
index d7cc4613..60af1dde 100644
--- a/tooling/src/main/scala/io/github/arainko/tooling/Debug.scala
+++ b/tooling/src/main/scala/io/github/arainko/tooling/Debug.scala
@@ -76,10 +76,6 @@ private[ducktape] object Debug {
       s"Deferred(...)"
   }
 
-  given function: Debug[Nothing => Any] with {
-    extension (self: Nothing => Any) def show(using Quotes): String = s"Function(...)"
-  }
-
   given expr[A]: Debug[Expr[A]] with {
     extension (value: Expr[A]) def show(using Quotes): String = {
       import quotes.reflect.*