diff --git a/compiler/src/dotty/tools/dotc/typer/TypeAssigner.scala b/compiler/src/dotty/tools/dotc/typer/TypeAssigner.scala
index 1ce0f6376b95..be6a43de3976 100644
--- a/compiler/src/dotty/tools/dotc/typer/TypeAssigner.scala
+++ b/compiler/src/dotty/tools/dotc/typer/TypeAssigner.scala
@@ -140,9 +140,19 @@ trait TypeAssigner {
     val name = tree.name
     val pre = maybeSkolemizePrefix(qualType, name)
     val mbr = qualType.findMember(name, pre)
+    def isDynamicExpansion(tree: untpd.RefTree): Boolean = {
+      Dynamic.isDynamicMethod(name) || (
+        tree match
+          case Select(Apply(fun: untpd.RefTree, _), nme.apply) if defn.isContextFunctionClass(fun.symbol.owner) =>
+            isDynamicExpansion(fun)
+          case  Select(qual, nme.apply) =>
+            Dynamic.isDynamicMethod(qual.symbol.name) && tree.span.isSynthetic
+          case _ => false
+      )
+    }
     if (reallyExists(mbr))
       qualType.select(name, mbr)
-    else if (qualType.derivesFrom(defn.DynamicClass) && name.isTermName && !Dynamic.isDynamicMethod(name))
+    else if (qualType.derivesFrom(defn.DynamicClass) && name.isTermName && !isDynamicExpansion(tree))
       TryDynamicCallType
     else if (qualType.isErroneous || name.toTermName == nme.ERROR)
       UnspecifiedErrorType
diff --git a/tests/neg/i9295a.scala b/tests/neg/i9295a.scala
new file mode 100644
index 000000000000..86acc959f931
--- /dev/null
+++ b/tests/neg/i9295a.scala
@@ -0,0 +1,9 @@
+import scala.language.dynamics
+
+class Foo extends Dynamic {
+  def applyDynamic(arg: Any): Foo = ???
+}
+object F {
+  val foo = new Foo
+  def baz = foo.blah(43) // error: method applyDynamic in class Foo does not take more parameters
+}
diff --git a/tests/neg/i9295b.scala b/tests/neg/i9295b.scala
new file mode 100644
index 000000000000..24a5c81eaede
--- /dev/null
+++ b/tests/neg/i9295b.scala
@@ -0,0 +1,14 @@
+import scala.language.dynamics
+
+class Foo extends Dynamic {
+  def applyDynamic(arg: Any): Bar = ???
+}
+class Bar extends Dynamic {
+  def applyDynamic(arg: Any)(x: Int): Int = ???
+}
+object F {
+  val foo = new Foo
+  def baz = foo.blah(43) // error: method applyDynamic in class Foo does not take more parameters
+  def qux = foo.blah.blah(43) // error: value selectDynamic is not a member of Foo
+  def quxx = foo.blah().blah(43) // error: method applyDynamic in class Foo does not take more parameters
+}
diff --git a/tests/neg/i9295c.scala b/tests/neg/i9295c.scala
new file mode 100644
index 000000000000..701b84fa4bcc
--- /dev/null
+++ b/tests/neg/i9295c.scala
@@ -0,0 +1,12 @@
+import scala.language.dynamics
+
+class Foo extends Dynamic {
+  def selectDynamic(name: String)(using DummyImplicit): Bar = ???
+}
+
+class Bar extends Dynamic {
+  def applyDynamic(name: String)(x: Int) = ???
+}
+
+val foo = new Foo
+def baz = foo.blah(42) // error
diff --git a/tests/neg/i9295d.scala b/tests/neg/i9295d.scala
new file mode 100644
index 000000000000..28c64d8fb77a
--- /dev/null
+++ b/tests/neg/i9295d.scala
@@ -0,0 +1,12 @@
+import scala.language.dynamics
+
+class Foo extends Dynamic {
+  def applyDynamic(name: String)(): DummyImplicit ?=> Bar = ???
+}
+
+class Bar extends Dynamic {
+  def applyDynamic(name: String)(x: Int) = ???
+}
+
+val foo = new Foo
+def baz = foo.blah()(42) // error
diff --git a/tests/pos/i9295.scala b/tests/pos/i9295.scala
new file mode 100644
index 000000000000..654ff1dc00d5
--- /dev/null
+++ b/tests/pos/i9295.scala
@@ -0,0 +1,12 @@
+import scala.language.dynamics
+
+class Foo extends Dynamic {
+  def applyDynamic(name: String)(): Bar = ???
+}
+
+class Bar extends Dynamic {
+  def applyDynamic(name: String)(x: Int) = ???
+}
+
+val foo = new Foo
+def baz = foo.blah().apply(42)
diff --git a/tests/pos/i9295b.scala b/tests/pos/i9295b.scala
new file mode 100644
index 000000000000..071875b7fa24
--- /dev/null
+++ b/tests/pos/i9295b.scala
@@ -0,0 +1,12 @@
+import scala.language.dynamics
+
+class Foo extends Dynamic {
+  def applyDynamic(name: String)()(using DummyImplicit): Bar = ???
+}
+
+class Bar extends Dynamic {
+  def applyDynamic(name: String)(x: Int) = ???
+}
+
+val foo = new Foo
+def baz = foo.blah().apply(42)
diff --git a/tests/pos/i9295c.scala b/tests/pos/i9295c.scala
new file mode 100644
index 000000000000..f0e86339bf4c
--- /dev/null
+++ b/tests/pos/i9295c.scala
@@ -0,0 +1,12 @@
+import scala.language.dynamics
+
+class Foo extends Dynamic {
+  def selectDynamic(name: String)(using DummyImplicit): Bar = ???
+}
+
+class Bar extends Dynamic {
+  def applyDynamic(name: String)(x: Int) = ???
+}
+
+val foo = new Foo
+def baz = foo.blah.apply(42)
diff --git a/tests/pos/i9295d.scala b/tests/pos/i9295d.scala
new file mode 100644
index 000000000000..8488d71cc067
--- /dev/null
+++ b/tests/pos/i9295d.scala
@@ -0,0 +1,12 @@
+import scala.language.dynamics
+
+class Foo extends Dynamic {
+  def applyDynamic(name: String)(): DummyImplicit ?=> DummyImplicit ?=> Bar = ???
+}
+
+class Bar extends Dynamic {
+  def applyDynamic(name: String)(x: Int) = ???
+}
+
+val foo = new Foo
+def baz = foo.blah().apply(42)