diff --git a/compiler/src/dotty/tools/dotc/core/Definitions.scala b/compiler/src/dotty/tools/dotc/core/Definitions.scala
index a81f4be9068a..8aacbee09bc0 100644
--- a/compiler/src/dotty/tools/dotc/core/Definitions.scala
+++ b/compiler/src/dotty/tools/dotc/core/Definitions.scala
@@ -958,6 +958,7 @@ class Definitions {
   def TupleClass(using Context): ClassSymbol = TupleTypeRef.symbol.asClass
     @tu lazy val Tuple_cons: Symbol = TupleClass.requiredMethod("*:")
   @tu lazy val TupleModule: Symbol = requiredModule("scala.Tuple")
+    @tu lazy val Tuple_Elem: Symbol = TupleModule.requiredType("Elem")
   @tu lazy val EmptyTupleClass: Symbol = requiredClass("scala.EmptyTuple")
   @tu lazy val EmptyTupleModule: Symbol = requiredModule("scala.EmptyTuple")
   @tu lazy val NonEmptyTupleTypeRef: TypeRef = requiredClassRef("scala.NonEmptyTuple")
@@ -1270,6 +1271,32 @@ class Definitions {
       else None
   }
 
+  // Pattern matcher of tuple selectors at the type level
+  // Matches Tuple.Elem[x, constant] and x._1.type
+  object TupleSelectorOf:
+    def unapply(tp: Type)(using Context): Option[(Type, Int)] =
+      if tp.isRef(Tuple_Elem) then
+        // get the arg infos for tuple elem
+        tp.argInfos match
+          case tupleType :: ConstantType(c) :: Nil
+            if c.isIntRange && (isTupleNType(tupleType) || tupleType.isRef(PairClass)) =>
+              Some((tupleType, c.intValue))
+          // we should probably report an error here, but its probably handled elsewhere
+          case _ => None
+      else
+        tp.dealias match
+          // very explicitly ONLY check for isTupleNType
+          // pair class doesn't have selector fields
+          case TermRef(tupleType, field) if isTupleNType(tupleType) =>
+            field match
+              case name: SimpleName =>
+                name.toString match
+                  case s"_$id" =>
+                    id.toIntOption.map(it => (tupleType, it - 1))
+                  case _ => None
+              case _ => None
+          case _ => None
+
   object ArrayOf {
     def apply(elem: Type)(using Context): Type =
       if (ctx.erasedTypes) JavaArrayType(elem)
@@ -1473,7 +1500,7 @@ class Definitions {
   def patchStdLibClass(denot: ClassDenotation)(using Context): Unit =
     // Do not patch the stdlib files if we explicitly disable it
     // This is only to be used during the migration of the stdlib
-    if ctx.settings.YnoStdlibPatches.value then 
+    if ctx.settings.YnoStdlibPatches.value then
       return
 
     def patch2(denot: ClassDenotation, patchCls: Symbol): Unit =
diff --git a/compiler/src/dotty/tools/dotc/typer/Synthesizer.scala b/compiler/src/dotty/tools/dotc/typer/Synthesizer.scala
index 8df2fc1ed4b7..36fe7c0c3a78 100644
--- a/compiler/src/dotty/tools/dotc/typer/Synthesizer.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Synthesizer.scala
@@ -20,6 +20,7 @@ import ast.tpd.*
 import Synthesizer.*
 import sbt.ExtractDependencies.*
 import xsbti.api.DependencyContext.*
+import dotty.tools.dotc.core.Definitions.MaxTupleArity
 
 /** Synthesize terms for special classes */
 class Synthesizer(typer: Typer)(using @constructorOnly c: Context):
@@ -105,29 +106,89 @@ class Synthesizer(typer: Typer)(using @constructorOnly c: Context):
   val synthesizedTupleFunction: SpecialHandler = (formal, span) =>
     formal match
       case AppliedType(_, funArgs @ fun :: tupled :: Nil) =>
+        def doesFunctionTupleInto(baseFun: Type, actualArgs: List[Type],
+            actualRet: Type, tupled: Type) =
+          tupled =:= constructDependentTupleType(actualArgs, actualRet, defn.isContextFunctionType(baseFun))
+        def doesFunctionUntupleTo(baseFun: Type, actualArgs: List[Type],
+            actualRet: Type, untupled: Type) =
+              untupled =:= untupleDependentTupleType(actualArgs, actualRet, defn.isContextFunctionType(baseFun))
+
         def functionTypeEqual(baseFun: Type, actualArgs: List[Type],
             actualRet: Type, expected: Type) =
-          expected =:= defn.FunctionNOf(actualArgs, actualRet,
-            defn.isContextFunctionType(baseFun))
+          expected =:= defn.FunctionNOf(actualArgs, actualRet, defn.isContextFunctionType(baseFun))
+        def untupleDependentTupleType(args: List[Type], ret: Type, contextual: Boolean): Type =
+          val methodKind = if contextual then ContextualMethodType else MethodType
+
+          val arity = args.length
+          methodKind(args.indices.map(nme.syntheticParamName).toList)(
+            mt => args,
+            mt =>
+              val tpeMap = new TypeMap:
+                def apply(tp: Type): Type =
+                  tp match
+                    case defn.TupleSelectorOf(TermParamRef(_, paramNum), fieldNum) =>
+                      if fieldNum >= arity then
+                        NoType
+                      else
+                        mt.paramRefs(fieldNum)
+                    case _ => mapOver(tp)
+              tpeMap(ret)
+          )
+
+        def constructDependentTupleType(args: List[Type], ret: Type, contextual: Boolean): Type =
+          val methodKind = if contextual then ContextualMethodType else MethodType
+
+          methodKind(List(nme.syntheticParamName(0)))(
+            mt => List(defn.tupleType(args)),
+            mt =>
+              val tpeMap = new TypeMap:
+                def apply(tp: Type): Type =
+                  tp match
+                    case TermParamRef(binder, paramNum) =>
+                      mt.paramRefs(0).select(nme.selectorName(paramNum))
+                    case _ =>
+                      mapOver(tp)
+              tpeMap(ret)
+          ).toFunctionType()
+
         val arity: Int =
           if defn.isFunctionNType(fun) then
             // TupledFunction[(...) => R, ?]
-            fun.functionArgInfos match
-              case funArgs :+ funRet
-              if functionTypeEqual(fun, defn.tupleType(funArgs) :: Nil, funRet, tupled) =>
-                // TupledFunction[(...funArgs...) => funRet, ?]
-                funArgs.size
-              case _ => -1
+            // dont use functionArgInfos it dealiases and drops dependents
+
+            fun.dealias match
+              case defn.RefinedFunctionOf(method: MethodType) if doesFunctionTupleInto(fun, method.paramInfos, method.resType, tupled) =>
+                method.paramInfos.size
+              // poly types are unsupported
+              case defn.RefinedFunctionOf(_) => -1
+              case _ =>
+                fun.functionArgInfos match
+                  case funArgs :+ funRet
+                  if functionTypeEqual(fun, defn.tupleType(funArgs) :: Nil, funRet, tupled) =>
+                    // TupledFunction[(...funArgs...) => funRet, ?]
+                    funArgs.size
+                  case _ => -1
           else if defn.isFunctionNType(tupled) then
             // TupledFunction[?, (...) => R]
-            tupled.functionArgInfos match
-              case tupledArgs :: funRet :: Nil =>
-                tupledArgs.tupleElementTypes match
-                  case Some(funArgs) if functionTypeEqual(tupled, funArgs, funRet, fun) =>
-                    // TupledFunction[?, ((...funArgs...)) => funRet]
-                    funArgs.size
+            tupled.dealias match
+              case defn.RefinedFunctionOf(method: MethodType) =>
+                method.argInfos match
+                  case tupledArgs :: funRet :: Nil =>
+                    // TupledFunction[?, ((...)) => R]
+                    tupledArgs.tupleElementTypes match
+                      case Some(args) if doesFunctionUntupleTo(tupled, args, funRet, fun) =>
+                        args.size
+                      case _ => -1
+                  case _ => -1
+              case _ =>
+                tupled.functionArgInfos match
+                  case tupledArgs :: funRet :: Nil =>
+                    // TupledFunction[?, ((...)) => R]
+                    tupledArgs.tupleElementTypes match
+                        case Some(args) if functionTypeEqual(tupled, args, funRet, fun) =>
+                          args.size
+                        case _ => -1
                   case _ => -1
-              case _ => -1
           else
             // TupledFunction[?, ?]
             -1
diff --git a/tests/neg/i21808a.check b/tests/neg/i21808a.check
new file mode 100644
index 000000000000..89dd43c92752
--- /dev/null
+++ b/tests/neg/i21808a.check
@@ -0,0 +1,4 @@
+-- [E172] Type Error: tests/neg/i21808a.scala:9:63 ---------------------------------------------------------------------
+9 |  summon[TupledFunction[(x: T, y: T) => x.type, ((T, T)) => T]] // error
+  |                                                               ^
+  |                                 (x: Test.T, y: Test.T) => x.type cannot be tupled as ((Test.T, Test.T)) => Test.T
diff --git a/tests/neg/i21808a.scala b/tests/neg/i21808a.scala
new file mode 100644
index 000000000000..df4cf3d5cb90
--- /dev/null
+++ b/tests/neg/i21808a.scala
@@ -0,0 +1,10 @@
+//> using options -experimental
+
+import scala.util.TupledFunction
+import scala.util.NotGiven
+
+object Test {
+  type T
+
+  summon[TupledFunction[(x: T, y: T) => x.type, ((T, T)) => T]] // error
+}
\ No newline at end of file
diff --git a/tests/neg/i21808b.check b/tests/neg/i21808b.check
new file mode 100644
index 000000000000..02d04b43b977
--- /dev/null
+++ b/tests/neg/i21808b.check
@@ -0,0 +1,4 @@
+-- [E172] Type Error: tests/neg/i21808b.scala:9:63 ---------------------------------------------------------------------
+9 |  summon[TupledFunction[(T, T) => T, (x: (T, T)) => x._1.type]] // error
+  |                                                               ^
+  |                           (Test.T, Test.T) => Test.T cannot be tupled as (x: (Test.T, Test.T)) => (x._1 : Test.T)
diff --git a/tests/neg/i21808b.scala b/tests/neg/i21808b.scala
new file mode 100644
index 000000000000..3042ab16abf0
--- /dev/null
+++ b/tests/neg/i21808b.scala
@@ -0,0 +1,10 @@
+//> using options -experimental
+
+import scala.util.TupledFunction
+import scala.util.NotGiven
+
+object Test {
+  type T
+
+  summon[TupledFunction[(T, T) => T, (x: (T, T)) => x._1.type]] // error
+}
\ No newline at end of file
diff --git a/tests/pos/i21808.scala b/tests/pos/i21808.scala
new file mode 100644
index 000000000000..fde33c858b82
--- /dev/null
+++ b/tests/pos/i21808.scala
@@ -0,0 +1,10 @@
+//> using options -experimental
+
+import scala.util.TupledFunction
+import scala.util.NotGiven
+
+object Test {
+  type T
+
+  summon[TupledFunction[(x: T, y: T) => x.type, (x: (T, T)) => x._1.type]]
+}
\ No newline at end of file