diff --git a/modules/build/src/test/scala/scala/build/tests/BuildTests.scala b/modules/build/src/test/scala/scala/build/tests/BuildTests.scala
index 47a9ed9ca8..b940c103ae 100644
--- a/modules/build/src/test/scala/scala/build/tests/BuildTests.scala
+++ b/modules/build/src/test/scala/scala/build/tests/BuildTests.scala
@@ -625,10 +625,24 @@ abstract class BuildTests(server: Boolean) extends TestUtil.ScalaCliBuildSuite {
   }
 
   test("cli scalac options shadowing using directives") {
-    val cliScalacOptions            = Seq("-Xmaxwarns", "4", "-g:source")
-    val usingDirectiveScalacOptions = Seq("-nobootcp", "-Xmaxwarns", "5", "-g:none")
+    val cliScalacOptions = Seq("-Xmaxwarns", "4", "-g:source", "-language:no2AutoTupling")
+    val usingDirectiveScalacOptions = Seq(
+      "-nobootcp",
+      "-Xmaxwarns",
+      "5",
+      "-g:none",
+      "-language:no2AutoTupling",
+      "-language:strictEquality"
+    )
 
-    val expectedOptions = Seq("-Xmaxwarns", "4", "-g:source", "-nobootcp")
+    val expectedOptions = Seq(
+      "-Xmaxwarns",
+      "4",
+      "-g:source",
+      "-language:no2AutoTupling",
+      "-nobootcp",
+      "-language:strictEquality"
+    )
 
     val inputs = TestInputs(
       os.rel / "foo.scala" ->
@@ -650,7 +664,7 @@ abstract class BuildTests(server: Boolean) extends TestUtil.ScalaCliBuildSuite {
       assert(maybeBuild.isRight)
       val build         = maybeBuild.toOption.get
       val scalacOptions = build.options.scalaOptions.scalacOptions.toSeq.map(_.value.value)
-      expect(scalacOptions == expectedOptions)
+      assertEquals(scalacOptions, expectedOptions)
     }
   }
 
diff --git a/modules/options/src/main/scala/scala/build/options/ScalacOpt.scala b/modules/options/src/main/scala/scala/build/options/ScalacOpt.scala
index 466142bb62..e1d7b0611f 100644
--- a/modules/options/src/main/scala/scala/build/options/ScalacOpt.scala
+++ b/modules/options/src/main/scala/scala/build/options/ScalacOpt.scala
@@ -8,8 +8,9 @@ final case class ScalacOpt(value: String) {
     else Some("@").filter(value.startsWith)
 
   /** @return raw key for the option (only if the key can be shadowed from the CLI) */
-  private[options] def shadowableKey: Option[String] =
-    key.filterNot(key => ScalacOpt.repeatingKeys.exists(_.startsWith(key)))
+  private[options] def shadowableKey: Option[String] = key match
+    case Some(key) if ScalacOpt.repeatingKeys.exists(_.startsWith(key)) => Some(value)
+    case otherwise                                                      => otherwise
 }
 
 object ScalacOpt {