diff --git a/compiler/src/dotty/tools/dotc/typer/Typer.scala b/compiler/src/dotty/tools/dotc/typer/Typer.scala
index 4e39335cc216..fd29f323c9fe 100644
--- a/compiler/src/dotty/tools/dotc/typer/Typer.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Typer.scala
@@ -1137,12 +1137,9 @@ class Typer(@constructorOnly nestingLevel: Int = 0) extends Namer
 
             val setter = toSetter(lhsCore)
             if setter.isEmpty then reassignmentToVal
-            else tryEither {
+            else
               val assign = untpd.Apply(setter, tree.rhs :: Nil)
               typed(assign, IgnoredProto(pt))
-            } {
-              (_, _) => reassignmentToVal
-            }
           case _ => lhsCore.tpe match {
             case ref: TermRef =>
               val lhsVal = lhsCore.denot.suchThat(!_.is(Method))
diff --git a/tests/neg/i20338a.check b/tests/neg/i20338a.check
new file mode 100644
index 000000000000..a329492bd990
--- /dev/null
+++ b/tests/neg/i20338a.check
@@ -0,0 +1,7 @@
+-- [E007] Type Mismatch Error: tests/neg/i20338a.scala:10:15 -----------------------------------------------------------
+10 |  test.field = "hello" // error
+   |               ^^^^^^^
+   |               Found:    ("hello" : String)
+   |               Required: Int
+   |
+   | longer explanation available when compiling with `-explain`
diff --git a/tests/neg/i20338a.scala b/tests/neg/i20338a.scala
new file mode 100644
index 000000000000..b91982297d78
--- /dev/null
+++ b/tests/neg/i20338a.scala
@@ -0,0 +1,10 @@
+object types:
+  opaque type Struct = Int
+  val test: Struct = 25
+  extension (s: Struct) 
+    def field: Int = s
+    def field_=(other: Int) = ()
+
+@main def hello = 
+  import types.*
+  test.field = "hello" // error
\ No newline at end of file
diff --git a/tests/neg/i20338b.check b/tests/neg/i20338b.check
new file mode 100644
index 000000000000..382d68a0911c
--- /dev/null
+++ b/tests/neg/i20338b.check
@@ -0,0 +1,7 @@
+-- [E007] Type Mismatch Error: tests/neg/i20338b.scala:10:8 ------------------------------------------------------------
+10 |  f.x = 42 // error
+   |        ^^
+   |        Found:    (42 : Int)
+   |        Required: String
+   |
+   | longer explanation available when compiling with `-explain`
diff --git a/tests/neg/i20338b.scala b/tests/neg/i20338b.scala
new file mode 100644
index 000000000000..b8a3463862e0
--- /dev/null
+++ b/tests/neg/i20338b.scala
@@ -0,0 +1,10 @@
+class Foo(_x: Int)
+
+extension (s: Foo)
+  def x_=(x: String): Unit = ()
+  def x: Int = ???
+
+@main
+def Test =
+  val f = Foo(42)
+  f.x = 42 // error
diff --git a/tests/neg/i20338c.check b/tests/neg/i20338c.check
new file mode 100644
index 000000000000..1d19ec0b3042
--- /dev/null
+++ b/tests/neg/i20338c.check
@@ -0,0 +1,6 @@
+-- [E052] Type Error: tests/neg/i20338c.scala:9:6 ----------------------------------------------------------------------
+9 |  f.x = 42 // error
+  |  ^^^^^^^^
+  |  Reassignment to val x
+  |
+  | longer explanation available when compiling with `-explain`
diff --git a/tests/neg/i20338c.scala b/tests/neg/i20338c.scala
new file mode 100644
index 000000000000..cfdf38e73b11
--- /dev/null
+++ b/tests/neg/i20338c.scala
@@ -0,0 +1,9 @@
+class Foo(val x: Int)
+
+extension (s: Foo)
+  def x: Int = 43
+
+@main
+def Test =
+  val f = Foo(42)
+  f.x = 42 // error
\ No newline at end of file