diff --git a/compiler/src/dotty/tools/dotc/transform/VCInlineMethods.scala b/compiler/src/dotty/tools/dotc/transform/VCInlineMethods.scala
index fb1dd04bd6ad..55b26d89b5a0 100644
--- a/compiler/src/dotty/tools/dotc/transform/VCInlineMethods.scala
+++ b/compiler/src/dotty/tools/dotc/transform/VCInlineMethods.scala
@@ -7,6 +7,7 @@ import core.*
 import Contexts.*, Trees.*, Types.*
 import DenotTransformers.*, MegaPhase.*
 import ExtensionMethods.*, ValueClasses.*
+import Decorators.*
 
 
 /** This phase inlines calls to methods of value classes.
@@ -58,12 +59,18 @@ class VCInlineMethods extends MiniPhase with IdentityDenotTransformer {
    */
   private def rewire(tree: Tree, mtArgs: List[Tree] = Nil, mArgss: List[List[Tree]] = Nil)
     (using Context): Tree =
+    def noTypeApplyIn(tree: Tree): Boolean = tree match
+      case _: TypeApply => false
+      case Apply(fn, _) => noTypeApplyIn(fn)
+      case _ => true
     tree match {
       case Apply(qual, mArgs) =>
         rewire(qual, mtArgs, mArgs :: mArgss)
       case TypeApply(qual, mtArgs2) =>
-        assert(mtArgs == Nil)
-        rewire(qual, mtArgs2, mArgss)
+        if noTypeApplyIn(qual) then
+          rewire(qual, mtArgs2, mArgss)
+        else
+          rewire(qual, mtArgs, mtArgs2 :: mArgss)
       case sel @ Select(qual, _) =>
         val origMeth = sel.symbol
         val origCls = origMeth.enclosingClass
diff --git a/compiler/test/dotc/pos-test-pickling.excludelist b/compiler/test/dotc/pos-test-pickling.excludelist
index 1a0be6f66183..9706f95cdfb9 100644
--- a/compiler/test/dotc/pos-test-pickling.excludelist
+++ b/compiler/test/dotc/pos-test-pickling.excludelist
@@ -139,7 +139,7 @@ parsercombinators-new-syntax.scala
 hylolib-deferred-given
 hylolib-cb
 hylolib
-i23266.scala
+i23299.scala
 
 # typecheckErrors method unpickling
 i21415.scala
diff --git a/tests/pos/i23266.scala b/tests/pos/i23266.scala
index bc643ac7215d..3ff104c65cd7 100644
--- a/tests/pos/i23266.scala
+++ b/tests/pos/i23266.scala
@@ -1,17 +1,8 @@
+//> using scala 3.7.0
 
-def kek(t: Table, ids: t.Id*) = ???
+class Foo(v: Any) extends AnyVal:
+  def bar[X](bar: X)[Y]: Any = v
 
-trait Table {
-  type Id = String
-}
-
-object Table1 extends Table {
-  val id: Id = "table1_id"
-}
-
-class Table2() extends Table {
-  val id: Id = "table2_id"
-}
-
-val x = kek(Table1, Table1.id)
-val y = kek(Table2(), Table2().id)
\ No newline at end of file
+@main def run: Unit =
+  val f = new Foo("lol")
+  println(f.bar[String]("")[Boolean])
\ No newline at end of file
diff --git a/tests/pos/i23299.scala b/tests/pos/i23299.scala
new file mode 100644
index 000000000000..bc643ac7215d
--- /dev/null
+++ b/tests/pos/i23299.scala
@@ -0,0 +1,17 @@
+
+def kek(t: Table, ids: t.Id*) = ???
+
+trait Table {
+  type Id = String
+}
+
+object Table1 extends Table {
+  val id: Id = "table1_id"
+}
+
+class Table2() extends Table {
+  val id: Id = "table2_id"
+}
+
+val x = kek(Table1, Table1.id)
+val y = kek(Table2(), Table2().id)
\ No newline at end of file