diff --git a/compiler/src/dotty/tools/dotc/ast/MainProxies.scala b/compiler/src/dotty/tools/dotc/ast/MainProxies.scala
index 81612b8276a0..bbac310470c1 100644
--- a/compiler/src/dotty/tools/dotc/ast/MainProxies.scala
+++ b/compiler/src/dotty/tools/dotc/ast/MainProxies.scala
@@ -39,6 +39,13 @@ object MainProxies {
     mainMethods(stats).flatMap(mainProxy)
   }
 
+  private def checkNoShadowing(mainFun: Symbol)(using Context) =
+    val cls = ctx.typer.findRef(mainFun.name.toTypeName, WildcardType, EmptyFlags, mainFun).typeSymbol
+    if cls.exists && cls.owner != ctx.owner then
+      report.warning(
+        i"""The class `${ctx.printer.fullNameString(mainFun)}` generated from `@main` will shadow the existing ${cls.showLocated}.
+           |The existing definition might no longer be found on recompile.""", mainFun)
+
   import untpd._
   def mainProxy(mainFun: Symbol)(using Context): List[TypeDef] = {
     val mainAnnotSpan = mainFun.getAnnotation(defn.MainAnnot).get.tree.span
@@ -86,6 +93,7 @@ object MainProxies {
         case _ =>
           report.error(s"@main can only annotate a method", pos)
       }
+      checkNoShadowing(mainFun)
       val errVar = Ident(nme.error)
       val handler = CaseDef(
         Typed(errVar, TypeTree(defn.CLP_ParseError.typeRef)),
diff --git a/compiler/src/dotty/tools/dotc/printing/RefinedPrinter.scala b/compiler/src/dotty/tools/dotc/printing/RefinedPrinter.scala
index 3da41b003adb..e214677a7b98 100644
--- a/compiler/src/dotty/tools/dotc/printing/RefinedPrinter.scala
+++ b/compiler/src/dotty/tools/dotc/printing/RefinedPrinter.scala
@@ -84,7 +84,7 @@ class RefinedPrinter(_ctx: Context) extends PlainPrinter(_ctx) {
     nameString(if (ctx.property(XprintMode).isEmpty) sym.initial.name else sym.name)
 
   override def fullNameString(sym: Symbol): String =
-    if (isEmptyPrefix(sym.maybeOwner)) nameString(sym)
+    if !sym.exists || isEmptyPrefix(sym.effectiveOwner) then nameString(sym)
     else super.fullNameString(sym)
 
   override protected def fullNameOwner(sym: Symbol): Symbol = {
diff --git a/compiler/src/dotty/tools/dotc/typer/Typer.scala b/compiler/src/dotty/tools/dotc/typer/Typer.scala
index a8ae701e3a27..dac701f4d53e 100644
--- a/compiler/src/dotty/tools/dotc/typer/Typer.scala
+++ b/compiler/src/dotty/tools/dotc/typer/Typer.scala
@@ -2241,11 +2241,12 @@ class Typer extends Namer
     val pkg = pid1.symbol
     pid1 match
       case pid1: RefTree if pkg.is(Package) =>
-        val packageCtx = ctx.packageContext(tree, pkg)
-        var stats1 = typedStats(tree.stats, pkg.moduleClass)(using packageCtx)._1
-        if (!ctx.isAfterTyper)
-          stats1 = stats1 ++ typedBlockStats(MainProxies.mainProxies(stats1))(using packageCtx)._1
-        cpy.PackageDef(tree)(pid1, stats1).withType(pkg.termRef)
+        inContext(ctx.packageContext(tree, pkg)) {
+          var stats1 = typedStats(tree.stats, pkg.moduleClass)._1
+          if (!ctx.isAfterTyper)
+            stats1 = stats1 ++ typedBlockStats(MainProxies.mainProxies(stats1))._1
+          cpy.PackageDef(tree)(pid1, stats1).withType(pkg.termRef)
+        }
       case _ =>
         // Package will not exist if a duplicate type has already been entered, see `tests/neg/1708.scala`
         errorTree(tree,
diff --git a/tests/neg-custom-args/fatal-warnings/i10137.check b/tests/neg-custom-args/fatal-warnings/i10137.check
new file mode 100644
index 000000000000..15361f8dbed2
--- /dev/null
+++ b/tests/neg-custom-args/fatal-warnings/i10137.check
@@ -0,0 +1,10 @@
+-- Error: tests/neg-custom-args/fatal-warnings/i10137.scala:2:12 -------------------------------------------------------
+2 |  @main def main(): Unit = println("Hello, World!") // error
+  |            ^
+  |            The class `foo.main` generated from `@main` will shadow the existing class main in package scala.
+  |            The existing definition might no longer be found on recompile.
+-- Error: tests/neg-custom-args/fatal-warnings/i10137.scala:4:10 -------------------------------------------------------
+4 |@main def List(): Unit = println("List") // error
+  |          ^
+  |          The class `List` generated from `@main` will shadow the existing type List in package scala.
+  |          The existing definition might no longer be found on recompile.
diff --git a/tests/neg-custom-args/fatal-warnings/i10137.scala b/tests/neg-custom-args/fatal-warnings/i10137.scala
new file mode 100644
index 000000000000..3272c3434e07
--- /dev/null
+++ b/tests/neg-custom-args/fatal-warnings/i10137.scala
@@ -0,0 +1,4 @@
+package foo:
+  @main def main(): Unit = println("Hello, World!") // error
+
+@main def List(): Unit = println("List") // error
diff --git a/tests/pending/pos/i10161.scala b/tests/pending/pos/i10161.scala
new file mode 100644
index 000000000000..0bbc78b1b354
--- /dev/null
+++ b/tests/pending/pos/i10161.scala
@@ -0,0 +1,18 @@
+object Incompat2 {
+  trait Context { type Out }
+
+  object Context {
+    def foo(implicit ctx: Context): Option[ctx.Out] = ???
+
+    def bar(implicit ctx: Context): (Option[ctx.Out], String) = (foo, "foo")
+  }
+}
+object Incompat3 {
+  trait Context { type Out }
+
+  object Context {
+    given foo(using ctx: Context) as Option[ctx.Out] = ???
+
+    given bar(using ctx: Context) as (Option[ctx.Out], String) = (foo, "foo")
+  }
+}
\ No newline at end of file