diff --git a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/ErrorMessage.scala b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/ErrorMessage.scala
index 5ce5d67a..bc9ee190 100644
--- a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/ErrorMessage.scala
+++ b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/ErrorMessage.scala
@@ -94,4 +94,14 @@ private[ducktape] object ErrorMessage {
       "Case config's path should always end with an `.at` segment"
     val side: Side = Side.Source
   }
+
+  case object LoopingTransformerDetected extends ErrorMessage {
+    val side: Side = Side.Dest
+
+    def render(using Quotes): String =
+      "Detected usage of `_.to[B]`, `_.fallibleTo[B]`, `_.into[B].transform()` or `_.into[B].fallible.transform()` in a given Transformer definition which results in a self-looping Transformer. Please use `Transformer.define[A, B]` or `Transformer.define[A, B].fallible` (for some types A and B) to create Transformer definitions"
+
+    val span: Span | None.type = None
+  }
+
 }
diff --git a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Planner.scala b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Planner.scala
index 47b60fe2..98d9f1b3 100644
--- a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Planner.scala
+++ b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/Planner.scala
@@ -1,8 +1,11 @@
 package io.github.arainko.ducktape.internal
 
+import io.github.arainko.ducktape.internal.Plan.{ Derived, UserDefined }
+import io.github.arainko.ducktape.internal.Summoner.UserDefined.{ FallibleTransformer, TotalTransformer }
 import io.github.arainko.ducktape.internal.*
 
 import scala.quoted.*
+import scala.util.boundary
 
 private[ducktape] object Planner {
   import Structure.*
@@ -28,7 +31,7 @@ private[ducktape] object Planner {
           planProductFunctionTransformation(source, dest)
 
         case UserDefinedTransformation(transformer) =>
-          Plan.UserDefined(source, dest, transformer)
+          verifyNotSelfReferential(Plan.UserDefined(source, dest, transformer))
 
         case (source, dest) if source.tpe.repr <:< dest.tpe.repr =>
           Plan.Upcast(source, dest)
@@ -70,7 +73,7 @@ private[ducktape] object Planner {
           Plan.BetweenUnwrappedWrapped(source, dest)
 
         case DerivedTransformation(transformer) =>
-          Plan.Derived(source, dest, transformer)
+          verifyNotSelfReferential(Plan.Derived(source, dest, transformer))
 
         case (source, dest) =>
           Plan.Error(
@@ -157,13 +160,13 @@ private[ducktape] object Planner {
     def unapply[F <: Fallible](structs: (Structure, Structure))(using Quotes, Depth, TransformationSite, Summoner[F]) = {
       val (src, dest) = structs
 
-      def summonTransformer =
+      def summonTransformer(using Quotes) =
         (src.tpe -> dest.tpe) match {
           case '[src] -> '[dest] => Summoner[F].summonUserDefined[src, dest]
         }
 
       // if current depth is lower or equal to 1 then that means we're most likely referring to ourselves
-      summon[TransformationSite] match {
+      TransformationSite.current match {
         case TransformationSite.Definition if Depth.current <= 1 => None
         case TransformationSite.Definition                       => summonTransformer
         case TransformationSite.Transformation                   => summonTransformer
@@ -180,4 +183,31 @@ private[ducktape] object Planner {
       }
     }
   }
+
+  private def verifyNotSelfReferential(
+    plan: Plan.Derived[Fallible] | Plan.UserDefined[Fallible]
+  )(using TransformationSite, Depth, Quotes): Plan.Error | plan.type = {
+    import quotes.reflect.*
+
+    val transformerExpr = plan match
+      case UserDefined(source, dest, Summoner.UserDefined.TotalTransformer(t))    => t
+      case UserDefined(source, dest, Summoner.UserDefined.FallibleTransformer(t)) => t
+      case Derived(source, dest, Summoner.Derived.TotalTransformer(t))            => t
+      case Derived(source, dest, Summoner.Derived.FallibleTransformer(t))         => t
+
+    val transformerSymbol = transformerExpr.asTerm.symbol
+
+    TransformationSite.current match
+      case TransformationSite.Transformation if Depth.current == 1 =>
+        boundary[Plan.Error | plan.type]:
+          var owner = Symbol.spliceOwner
+          while (!owner.isNoSymbol) {
+            if owner == transformerSymbol then
+              boundary.break(Plan.Error.from(plan, ErrorMessage.LoopingTransformerDetected, None))
+            owner = owner.maybeOwner
+          }
+          plan
+      case _ => plan
+
+  }
 }
diff --git a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/TransformationSite.scala b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/TransformationSite.scala
index 0329041e..cb4a04d0 100644
--- a/ducktape/src/main/scala/io/github/arainko/ducktape/internal/TransformationSite.scala
+++ b/ducktape/src/main/scala/io/github/arainko/ducktape/internal/TransformationSite.scala
@@ -8,6 +8,8 @@ private[ducktape] enum TransformationSite {
 }
 
 private[ducktape] object TransformationSite {
+  def current(using ts: TransformationSite): TransformationSite = ts
+
   def fromStringExpr(value: Expr["transformation" | "definition"])(using Quotes): TransformationSite = {
     import quotes.reflect.*
 
diff --git a/ducktape/src/test/scala/io/github/arainko/ducktape/issues/Issue165Suite.scala b/ducktape/src/test/scala/io/github/arainko/ducktape/issues/Issue165Suite.scala
new file mode 100644
index 00000000..41bd1235
--- /dev/null
+++ b/ducktape/src/test/scala/io/github/arainko/ducktape/issues/Issue165Suite.scala
@@ -0,0 +1,57 @@
+package io.github.arainko.ducktape.issues
+
+import io.github.arainko.ducktape.*
+
+class Issue165Suite extends DucktapeSuite {
+  test("rejects _.to in given Transformer definitions") {
+    assertFailsToCompileWith {
+      """
+      case class A(a: Int)
+      case class B(b: Int)
+      given Transformer[A, B] = _.to[B]
+      """
+    }(
+      "Detected usage of `_.to[B]`, `_.fallibleTo[B]`, `_.into[B].transform()` or `_.into[B].fallible.transform()` in a given Transformer definition which results in a self-looping Transformer. Please use `Transformer.define[A, B]` or `Transformer.define[A, B].fallible` (for some types A and B) to create Transformer definitions @ B"
+    )
+  }
+
+  test("rejects _.into.transform() in given Transformer definitions") {
+    assertFailsToCompileWith {
+      """
+      case class A(a: Int)
+      case class B(b: Int)
+      given Transformer[A, B] = _.into[B].transform()
+      """
+    }(
+      "Detected usage of `_.to[B]`, `_.fallibleTo[B]`, `_.into[B].transform()` or `_.into[B].fallible.transform()` in a given Transformer definition which results in a self-looping Transformer. Please use `Transformer.define[A, B]` or `Transformer.define[A, B].fallible` (for some types A and B) to create Transformer definitions @ B"
+    )
+  }
+
+  test("rejects _.falibleTo in given Trasformer.Fallible definitions") {
+    assertFailsToCompileWith {
+      """
+      given Mode.FailFast.Option with {}
+
+      case class A(a: Int)
+      case class B(b: Int)
+      given Transformer.Fallible[Option, A, B] = _.fallibleTo[B]
+      """
+    }(
+      "Detected usage of `_.to[B]`, `_.fallibleTo[B]`, `_.into[B].transform()` or `_.into[B].fallible.transform()` in a given Transformer definition which results in a self-looping Transformer. Please use `Transformer.define[A, B]` or `Transformer.define[A, B].fallible` (for some types A and B) to create Transformer definitions @ B"
+    )
+  }
+
+  test("rejects _.into.falible in given Trasformer.Fallible definitions") {
+    assertFailsToCompileWith {
+      """
+      given Mode.FailFast.Option with {}
+
+      case class A(a: Int)
+      case class B(b: Int)
+      given Transformer.Fallible[Option, A, B] = _.into[B].fallible.transform()
+      """
+    }(
+      "Detected usage of `_.to[B]`, `_.fallibleTo[B]`, `_.into[B].transform()` or `_.into[B].fallible.transform()` in a given Transformer definition which results in a self-looping Transformer. Please use `Transformer.define[A, B]` or `Transformer.define[A, B].fallible` (for some types A and B) to create Transformer definitions @ B"
+    )
+  }
+}