diff --git a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
index 99d8bb2238d5..eb46876f10f8 100644
--- a/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
+++ b/compiler/src/dotty/tools/dotc/core/TypeComparer.scala
@@ -1575,7 +1575,7 @@ class TypeComparer(@constructorOnly initctx: Context) extends ConstraintHandling
    *  Note: It would be legal to do the lifting also if M does not contain opaque types,
    *  but in this case the retries in tryLiftedToThis would be redundant.
    */
-  private def liftToThis(tp: Type): Type = {
+  def liftToThis(tp: Type): Type = {
 
     def findEnclosingThis(moduleClass: Symbol, from: Symbol): Type =
       if ((from.owner eq moduleClass) && from.isPackageObject && from.is(Opaque)) from.thisType
diff --git a/compiler/src/dotty/tools/dotc/typer/Typer.scala b/compiler/src/dotty/tools/dotc/typer/Typer.scala
index f1db302e958c..96e3cc05c70d 100644
--- a/compiler/src/dotty/tools/dotc/typer/Typer.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Typer.scala
@@ -688,72 +688,92 @@ class Typer(@constructorOnly nestingLevel: Int = 0) extends Namer
     val tree = cpy.Select(tree0)(qual, selName)
     val superAccess = qual.isInstanceOf[Super]
     val rawType = selectionType(tree, qual)
-    val checkedType = accessibleType(rawType, superAccess)
-
-    def finish(tree: untpd.Select, qual: Tree, checkedType: Type): Tree =
-      val select = toNotNullTermRef(assignType(tree, checkedType), pt)
-      if selName.isTypeName then checkStable(qual.tpe, qual.srcPos, "type prefix")
-      checkLegalValue(select, pt)
-      ConstFold(select)
-
-    if checkedType.exists then
-      finish(tree, qual, checkedType)
-    else if selName == nme.apply && qual.tpe.widen.isInstanceOf[MethodType] then
-      // Simplify `m.apply(...)` to `m(...)`
-      qual
-    else if couldInstantiateTypeVar(qual.tpe.widen) then
-       // there's a simply visible type variable in the result; try again with a more defined qualifier type
-       // There's a second trial where we try to instantiate all type variables in `qual.tpe.widen`,
-       // but that is done only after we search for extension methods or conversions.
-      typedSelect(tree, pt, qual)
-    else if qual.tpe.isSmallGenericTuple then
-      val elems = qual.tpe.widenTermRefExpr.tupleElementTypes.getOrElse(Nil)
-      typedSelect(tree, pt, qual.cast(defn.tupleType(elems)))
-    else
-      val tree1 = tryExtensionOrConversion(
-          tree, pt, IgnoredProto(pt), qual, ctx.typerState.ownedVars, this, inSelect = true)
-        .orElse {
-          if ctx.gadt.isNarrowing then
-            // try GADT approximation if we're trying to select a member
-            // Member lookup cannot take GADTs into account b/c of cache, so we
-            // approximate types based on GADT constraints instead. For an example,
-            // see MemberHealing in gadt-approximation-interaction.scala.
-            val wtp = qual.tpe.widen
-            gadts.println(i"Trying to heal member selection by GADT-approximating $wtp")
-            val gadtApprox = Inferencing.approximateGADT(wtp)
-            gadts.println(i"GADT-approximated $wtp ~~ $gadtApprox")
-            val qual1 = qual.cast(gadtApprox)
-            val tree1 = cpy.Select(tree0)(qual1, selName)
-            val checkedType1 = accessibleType(selectionType(tree1, qual1), superAccess = false)
-            if checkedType1.exists then
-              gadts.println(i"Member selection healed by GADT approximation")
-              finish(tree1, qual1, checkedType1)
-            else if qual1.tpe.isSmallGenericTuple then
-              gadts.println(i"Tuple member selection healed by GADT approximation")
-              typedSelect(tree, pt, qual1)
-            else
-              tryExtensionOrConversion(tree1, pt, IgnoredProto(pt), qual1, ctx.typerState.ownedVars, this, inSelect = true)
-          else EmptyTree
-        }
-      if !tree1.isEmpty then
-        tree1
-      else if canDefineFurther(qual.tpe.widen) then
-        typedSelect(tree, pt, qual)
-      else if qual.tpe.derivesFrom(defn.DynamicClass)
-        && selName.isTermName && !isDynamicExpansion(tree)
-      then
-        val tree2 = cpy.Select(tree0)(untpd.TypedSplice(qual), selName)
-        if pt.isInstanceOf[FunOrPolyProto] || pt == LhsProto then
-          assignType(tree2, TryDynamicCallType)
+
+    def tryType(tree: untpd.Select, qual: Tree, rawType: Type) =
+      val checkedType = accessibleType(rawType, superAccess)
+      if checkedType.exists then
+        val select = toNotNullTermRef(assignType(tree, checkedType), pt)
+        if selName.isTypeName then checkStable(qual.tpe, qual.srcPos, "type prefix")
+        checkLegalValue(select, pt)
+        ConstFold(select)
+      else EmptyTree
+
+    def trySmallGenericTuple(tree: untpd.Select, qual: Tree, withCast: Boolean) =
+      if qual.tpe.isSmallGenericTuple then
+        if withCast then
+          val elems = qual.tpe.widenTermRefExpr.tupleElementTypes.getOrElse(Nil)
+          typedSelect(tree, pt, qual.cast(defn.tupleType(elems)))
         else
-          typedDynamicSelect(tree2, Nil, pt)
-      else
-        assignType(tree,
-          rawType match
-            case rawType: NamedType =>
-              inaccessibleErrorType(rawType, superAccess, tree.srcPos)
-            case _ =>
-              notAMemberErrorType(tree, qual, pt))
+          typedSelect(tree, pt, qual)
+      else EmptyTree
+
+    def tryExt(tree: untpd.Select, qual: Tree) =
+      tryExtensionOrConversion(
+        tree, pt, IgnoredProto(pt), qual, ctx.typerState.ownedVars, this, inSelect = true)
+
+    def tryGadt(tree: untpd.Select) =
+      if ctx.gadt.isNarrowing then
+        // try GADT approximation if we're trying to select a member
+        // Member lookup cannot take GADTs into account b/c of cache, so we
+        // approximate types based on GADT constraints instead. For an example,
+        // see MemberHealing in gadt-approximation-interaction.scala.
+        val wtp = qual.tpe.widen
+        gadts.println(i"Trying to heal member selection by GADT-approximating $wtp")
+        val gadtApprox = Inferencing.approximateGADT(wtp)
+        gadts.println(i"GADT-approximated $wtp ~~ $gadtApprox")
+        val qual1 = qual.cast(gadtApprox)
+        val tree1 = cpy.Select(tree0)(qual1, selName)
+        tryType(tree1, qual1, selectionType(tree1, qual1))
+          .orElse(trySmallGenericTuple(tree, qual1, withCast = false))
+          .orElse(tryExt(tree1, qual1))
+      else EmptyTree
+
+    tryType(tree, qual, rawType)
+      .orElse {
+        if selName == nme.apply && qual.tpe.widen.isInstanceOf[MethodType] then
+          // Simplify `m.apply(...)` to `m(...)`
+          qual
+        else EmptyTree
+      }
+      .orElse {
+        if couldInstantiateTypeVar(qual.tpe.widen) then
+          // there's a simply visible type variable in the result; try again with a more defined qualifier type
+          // There's a second trial where we try to instantiate all type variables in `qual.tpe.widen`,
+          // but that is done only after we search for extension methods or conversions.
+          typedSelect(tree, pt, qual)
+        else EmptyTree
+      }
+      .orElse {
+        val wtp = qual.tpe.widen
+        val liftedTp = comparing(_.liftToThis(wtp))
+        if liftedTp ne wtp then
+          val qual1 = qual.cast(liftedTp)
+          val tree1 = cpy.Select(tree0)(qual1, selName)
+          val rawType1 = selectionType(tree1, qual1)
+          tryType(tree1, qual1, rawType1)
+        else EmptyTree
+      }
+      .orElse(trySmallGenericTuple(tree, qual, withCast = true))
+      .orElse(tryExt(tree, qual))
+      .orElse(tryGadt(tree))
+      .orElse:
+        if canDefineFurther(qual.tpe.widen) then
+          typedSelect(tree, pt, qual)
+        else if qual.tpe.derivesFrom(defn.DynamicClass)
+          && selName.isTermName && !isDynamicExpansion(tree)
+        then
+          val tree2 = cpy.Select(tree0)(untpd.TypedSplice(qual), selName)
+          if pt.isInstanceOf[FunOrPolyProto] || pt == LhsProto then
+            assignType(tree2, TryDynamicCallType)
+          else
+            typedDynamicSelect(tree2, Nil, pt)
+        else
+          assignType(tree,
+            rawType match
+              case rawType: NamedType =>
+                inaccessibleErrorType(rawType, superAccess, tree.srcPos)
+              case _ =>
+                notAMemberErrorType(tree, qual, pt))
   end typedSelect
 
   def typedSelect(tree: untpd.Select, pt: Type)(using Context): Tree = {
diff --git a/tests/pos/i19609.scala b/tests/pos/i19609.scala
new file mode 100644
index 000000000000..0879fa16c7cf
--- /dev/null
+++ b/tests/pos/i19609.scala
@@ -0,0 +1,24 @@
+object o { u =>
+  opaque type T = String
+
+  def st = summon[String =:= T]
+  def su = summon[String =:= u.T]
+  def so = summon[String =:= o.T]
+
+  def ts = summon[T =:= String]
+  def tu = summon[T =:= u.T]
+  def to = summon[T =:= o.T]
+
+  def us = summon[u.T =:= String]
+  def ut = summon[u.T =:= T]
+  def uo = summon[u.T =:= o.T]
+
+  def os = summon[o.T =:= String]
+  def ot = summon[o.T =:= T]
+  def ou = summon[o.T =:= u.T]
+
+  def ms(x: String): Int = x.length // ok
+  def mt(x:      T): Int = x.length // ok
+  def mu(x:    u.T): Int = x.length // ok
+  def mo(x:    o.T): Int = x.length // was: error: value length is not a member of o.T
+}