diff --git a/compiler/src/dotty/tools/dotc/typer/Applications.scala b/compiler/src/dotty/tools/dotc/typer/Applications.scala
index 35b8b1f9719d..8de3349931b6 100644
--- a/compiler/src/dotty/tools/dotc/typer/Applications.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Applications.scala
@@ -1002,7 +1002,10 @@ trait Applications extends Compatibility {
             case TypeApply(fun, _) => !fun.isInstanceOf[Select]
             case _ => false
           }
-          typedDynamicApply(tree, isInsertedApply, pt)
+          val tree1 = fun1 match
+            case Select(_, nme.apply) => tree
+            case _ => untpd.Apply(fun1, tree.args)
+          typedDynamicApply(tree1, isInsertedApply, pt)
         case _ =>
           if (originalProto.isDropped) fun1
           else if (fun1.symbol == defn.Compiletime_summonFrom)
diff --git a/tests/pos/i16544a.scala b/tests/pos/i16544a.scala
new file mode 100644
index 000000000000..b5afdaec75d0
--- /dev/null
+++ b/tests/pos/i16544a.scala
@@ -0,0 +1,49 @@
+import scala.language.dynamics
+
+object Foo extends Dynamic:
+  def applyDynamic(name: String)(): Foo.type = this
+
+object Test:
+  def test(): Foo.type =
+    Foo.xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
+      .xxx()
diff --git a/tests/pos/i16544b.scala b/tests/pos/i16544b.scala
new file mode 100644
index 000000000000..f8450e6dfa85
--- /dev/null
+++ b/tests/pos/i16544b.scala
@@ -0,0 +1,49 @@
+import scala.language.dynamics
+
+object Foo extends Dynamic:
+  def applyDynamicNamed(name: String)(args: (String, Int)): Foo.type = this
+
+object Test:
+  def test(): Foo.type =
+    Foo.xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
+      .xxx(a = 1)
diff --git a/tests/pos/i16544c.scala b/tests/pos/i16544c.scala
new file mode 100644
index 000000000000..5467d76918c7
--- /dev/null
+++ b/tests/pos/i16544c.scala
@@ -0,0 +1,49 @@
+import scala.language.dynamics
+
+object Foo extends Dynamic:
+  def selectDynamic(name: String): Foo.type = this
+
+object Test:
+  def test(): Foo.type =
+    Foo.xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
+      .xxx
diff --git a/tests/pos/i16544d.scala b/tests/pos/i16544d.scala
new file mode 100644
index 000000000000..1057df65e892
--- /dev/null
+++ b/tests/pos/i16544d.scala
@@ -0,0 +1,49 @@
+import scala.language.dynamics
+
+object Foo extends Dynamic:
+  def applyDynamic(name: String)(): Foo.type = this
+  def applyDynamicNamed(name: String)(args: (String, Int)): Foo.type = this
+  def selectDynamic(name: String): Foo.type = this
+
+object Test:
+  def test(): Foo.type =
+    Foo.xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx
+      .xxx()
+      .xxx(a = 1)
+      .xxx