diff --git a/compiler/src/dotty/tools/dotc/config/Settings.scala b/compiler/src/dotty/tools/dotc/config/Settings.scala
index 277833afbd5d..084d79ed4556 100644
--- a/compiler/src/dotty/tools/dotc/config/Settings.scala
+++ b/compiler/src/dotty/tools/dotc/config/Settings.scala
@@ -69,11 +69,11 @@ object Settings:
 
     def updateIn(state: SettingsState, x: Any): SettingsState = x match
       case _: T => state.update(idx, x)
-      case _ => throw IllegalArgumentException(s"found: $x of type ${x.getClass.getName}, required: ${implicitly[ClassTag[T]]}")
+      case _ => throw IllegalArgumentException(s"found: $x of type ${x.getClass.getName}, required: ${summon[ClassTag[T]]}")
 
     def isDefaultIn(state: SettingsState): Boolean = valueIn(state) == default
 
-    def isMultivalue: Boolean = implicitly[ClassTag[T]] == ListTag
+    def isMultivalue: Boolean = summon[ClassTag[T]] == ListTag
 
     def legalChoices: String =
       choices match {
@@ -106,6 +106,11 @@ object Settings:
       def missingArg =
         fail(s"missing argument for option $name", args)
 
+      def setBoolean(argValue: String, args: List[String]) =
+        if argValue.equalsIgnoreCase("true") || argValue.isEmpty then update(true, args)
+        else if argValue.equalsIgnoreCase("false") then update(false, args)
+        else fail(s"$argValue is not a valid choice for boolean setting $name", args)
+
       def setString(argValue: String, args: List[String]) =
         choices match
           case Some(xs) if !xs.contains(argValue) =>
@@ -126,9 +131,9 @@ object Settings:
         catch case _: NumberFormatException =>
           fail(s"$argValue is not an integer argument for $name", args)
 
-      def doSet(argRest: String) = ((implicitly[ClassTag[T]], args): @unchecked) match {
+      def doSet(argRest: String) = ((summon[ClassTag[T]], args): @unchecked) match {
         case (BooleanTag, _) =>
-          update(true, args)
+          setBoolean(argRest, args)
         case (OptionTag, _) =>
           update(Some(propertyClass.get.getConstructor().newInstance()), args)
         case (ListTag, _) =>
@@ -290,6 +295,6 @@ object Settings:
       publish(Setting(name, descr, default))
 
     def OptionSetting[T: ClassTag](name: String, descr: String, aliases: List[String] = Nil): Setting[Option[T]] =
-      publish(Setting(name, descr, None, propertyClass = Some(implicitly[ClassTag[T]].runtimeClass), aliases = aliases))
+      publish(Setting(name, descr, None, propertyClass = Some(summon[ClassTag[T]].runtimeClass), aliases = aliases))
   }
 end Settings
diff --git a/compiler/test/dotty/tools/dotc/SettingsTests.scala b/compiler/test/dotty/tools/dotc/SettingsTests.scala
index e3076f055d51..a42ee38a649a 100644
--- a/compiler/test/dotty/tools/dotc/SettingsTests.scala
+++ b/compiler/test/dotty/tools/dotc/SettingsTests.scala
@@ -179,6 +179,22 @@ class SettingsTests {
       assertEquals(100, foo.value)
     }
 
+  @Test def `Set BooleanSettings correctly`: Unit =
+    object Settings extends SettingGroup:
+      val foo = BooleanSetting("-foo", "foo", false)
+      val bar = BooleanSetting("-bar", "bar", true)
+      val baz = BooleanSetting("-baz", "baz", false)
+    import Settings._
+
+    val args = List("-foo:true", "-bar:false", "-baz")
+    val summary = processArguments(args, processAll = true)
+    assertTrue(s"Setting args errors:\n  ${summary.errors.take(5).mkString("\n  ")}", summary.errors.isEmpty)
+    withProcessedArgs(summary) {
+      assertEquals(true, foo.value)
+      assertEquals(false, bar.value)
+      assertEquals(true, baz.value)
+    }
+
   private def withProcessedArgs(summary: ArgsSummary)(f: SettingsState ?=> Unit) = f(using summary.sstate)
 
   extension [T](setting: Setting[T])