diff --git a/compiler/src/dotty/tools/dotc/ast/tpd.scala b/compiler/src/dotty/tools/dotc/ast/tpd.scala
index 1b4f982e9b0d..e0b282e2d8db 100644
--- a/compiler/src/dotty/tools/dotc/ast/tpd.scala
+++ b/compiler/src/dotty/tools/dotc/ast/tpd.scala
@@ -45,21 +45,19 @@ object tpd extends Trees.Instance[Type] with TypedTreeInfo {
   def Apply(fn: Tree, args: List[Tree])(using Context): Apply = fn match
     case Block(Nil, expr) =>
       Apply(expr, args)
+    case _: RefTree | _: GenericApply | _: Inlined | _: Hole =>
+      ta.assignType(untpd.Apply(fn, args), fn, args)
     case _ =>
-      assert(
-        fn.isInstanceOf[RefTree | GenericApply | Inlined | Hole] || ctx.reporter.errorsReported,
-        s"Illegal Apply function prefix: $fn"
-      )
+      assert(ctx.reporter.errorsReported)
       ta.assignType(untpd.Apply(fn, args), fn, args)
 
   def TypeApply(fn: Tree, args: List[Tree])(using Context): TypeApply = fn match
     case Block(Nil, expr) =>
       TypeApply(expr, args)
+    case _: RefTree | _: GenericApply =>
+      ta.assignType(untpd.TypeApply(fn, args), fn, args)
     case _ =>
-      assert(
-        fn.isInstanceOf[RefTree | GenericApply] || ctx.reporter.errorsReported,
-        s"Illegal TypeApply function prefix: $fn"
-      )
+      assert(ctx.reporter.errorsReported, s"unexpected tree for type application: $fn")
       ta.assignType(untpd.TypeApply(fn, args), fn, args)
 
   def Literal(const: Constant)(using Context): Literal =
diff --git a/compiler/src/dotty/tools/dotc/typer/Typer.scala b/compiler/src/dotty/tools/dotc/typer/Typer.scala
index 6a726432a4b0..6b10bedef532 100644
--- a/compiler/src/dotty/tools/dotc/typer/Typer.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Typer.scala
@@ -4366,7 +4366,13 @@ class Typer(@constructorOnly nestingLevel: Int = 0) extends Namer
             case _ =>
               adaptOverloaded(ref)
           }
-        case poly: PolyType if !(ctx.mode is Mode.Type) =>
+        case poly: PolyType
+        if !(ctx.mode is Mode.Type) && dummyTreeOfType.unapply(tree).isEmpty =>
+            // If we are in a conversion from a TermRef with polymorphic underlying
+        	  // type, give up. In this case the typed `null` literal cannot be instantiated.
+            // Test case was but i18695.scala, but it got fixed by a different tweak in #18719.
+            // We leave test for this condition in as a defensive measure in case
+            // it arises somewhere else.
           if isApplyProxy(tree) then newExpr
           else if pt.isInstanceOf[PolyProto] then tree
           else
diff --git a/tests/neg-macros/i18695.scala b/tests/neg-macros/i18695.scala
new file mode 100644
index 000000000000..7427839cdbe3
--- /dev/null
+++ b/tests/neg-macros/i18695.scala
@@ -0,0 +1,75 @@
+import scala.annotation.{tailrec, unused}
+import scala.deriving.Mirror
+import scala.quoted.*
+
+trait TypeLength[A] {
+  type Length <: Int
+  def length: Length
+}
+object TypeLength extends TypeLengthLowPriority:
+  type Aux[A, Length0 <: Int] = TypeLength[A] {
+    type Length = Length0
+  }
+
+  transparent inline given fromMirror[A](using m: Mirror.Of[A]): TypeLength[A] =
+    ${ macroImpl[A, m.MirroredElemTypes] }
+
+  @tailrec
+  private def typesOfTuple(
+      using q: Quotes
+  )(tpe: q.reflect.TypeRepr, acc: List[q.reflect.TypeRepr]): List[q.reflect.TypeRepr] =
+    import q.reflect.*
+    val cons = Symbol.classSymbol("scala.*:")
+    tpe.widenTermRefByName.dealias match
+      case AppliedType(fn, tpes) if defn.isTupleClass(fn.typeSymbol) =>
+        tpes.reverse_:::(acc)
+      case AppliedType(tp, List(headType, tailType)) if tp.derivesFrom(cons) =>
+        typesOfTuple(tailType, headType :: acc)
+      case tpe =>
+        if tpe.derivesFrom(Symbol.classSymbol("scala.EmptyTuple")) then acc.reverse
+        else report.errorAndAbort(s"Unknown type encountered in tuple ${tpe.show}")
+
+  def macroImpl[A: Type, T <: Tuple: scala.quoted.Type](
+      using q: scala.quoted.Quotes
+  ): scala.quoted.Expr[TypeLength[A]] =
+    import q.reflect.*
+    val l = typesOfTuple(TypeRepr.of[T], Nil).length
+    ConstantType(IntConstant(l)).asType match
+      case '[lt] =>
+        val le = Expr[Int](l).asExprOf[lt & Int]
+        '{
+          val r: TypeLength.Aux[A, lt & Int] = new TypeLength[A] {
+            type Length = lt & Int
+            val length: Length = ${ le }
+          }
+          r
+        }
+
+  transparent inline given fromTuple[T <: Tuple]: TypeLength[T] =
+    ${ macroImpl[T, T] }
+
+trait TypeLengthLowPriority:
+  self: TypeLength.type =>
+  given tupleFromMirrorAndLength[A, T <: Tuple](
+      using @unused m: Mirror.Of[A] { type MirroredElemTypes = T },
+      length: TypeLength[A]
+  ): TypeLength.Aux[T, length.Length] = length.asInstanceOf[TypeLength.Aux[T, length.Length]]
+
+trait HKDSumGeneric[A]
+object HKDSumGeneric:
+  type NotZero[N <: Int] = N match
+    case 0 => false
+    case _ => true
+
+  transparent inline given derived[A](using m: Mirror.SumOf[A], typeLength: TypeLength[A])(
+      using NotZero[typeLength.Length] =:= true
+  ): HKDSumGeneric[A] =
+    derivedImpl[A, m.MirroredElemTypes, m.MirroredLabel] // error
+
+  def derivedImpl[A, ElemTypes <: Tuple, Label <: String](
+      using m: Mirror.SumOf[A] {
+        type MirroredElemTypes = ElemTypes; type MirroredLabel = Label;
+      },
+      typeLength: TypeLength[ElemTypes],
+      nz: NotZero[typeLength.Length] =:= true
+  ): HKDSumGeneric[A] = ???
\ No newline at end of file
diff --git a/tests/neg/i18695.scala b/tests/neg/i18695.scala
new file mode 100644
index 000000000000..e10f30b26779
--- /dev/null
+++ b/tests/neg/i18695.scala
@@ -0,0 +1,3 @@
+trait Foo { type Num <: Int }
+given derived[A](using foo: Foo): Any = derivedImpl(foo)  // error
+def derivedImpl(foo: Foo)(using bar: foo.Num =:= Int): Any = ???