diff --git a/compiler/src/dotty/tools/dotc/printing/PlainPrinter.scala b/compiler/src/dotty/tools/dotc/printing/PlainPrinter.scala
index d9059bab77af..6d72cebf54c5 100644
--- a/compiler/src/dotty/tools/dotc/printing/PlainPrinter.scala
+++ b/compiler/src/dotty/tools/dotc/printing/PlainPrinter.scala
@@ -513,14 +513,29 @@ class PlainPrinter(_ctx: Context) extends Printer {
   def toTextPrefixOf(tp: NamedType): Text = controlled {
       homogenize(tp.prefix) match {
         case NoPrefix => ""
-        case tp: SingletonType => toTextRef(tp) ~ "."
-        case tp => trimPrefix(toTextLocal(tp)) ~ "#"
+        case prefix: SingletonType => toTextRef(prefix) ~ "."
+        case prefix =>
+          // Use "." for Java nested classes (e.g., java.util.Map.Entry)
+          // Use "#" for Scala type projections (e.g., Outer#Inner)
+          val separator = if (isJavaNestedClass(tp)) "." else "#"
+          trimPrefix(toTextLocal(prefix)) ~ separator
       }
   }
 
   protected def isEmptyPrefix(sym: Symbol): Boolean =
     sym.isEffectiveRoot || sym.isAnonymousClass || sym.name.isReplWrapperName
 
+  /** Check if tp represents a Java nested class that should use "." separator. */
+  protected def isJavaNestedClass(tp: NamedType)(using Context): Boolean = {
+    val sym = tp.symbol
+    sym.exists &&
+    sym.is(JavaDefined) &&
+    sym.isClass &&
+    sym.owner.exists &&
+    sym.owner.is(JavaDefined) &&
+    sym.owner.isClass
+  }
+
   /** String representation of a definition's type following its name,
    *  if symbol is completed, ": ?" otherwise.
    */
diff --git a/tests/neg/i24711-java-nested-types.check b/tests/neg/i24711-java-nested-types.check
new file mode 100644
index 000000000000..005a0ab71e52
--- /dev/null
+++ b/tests/neg/i24711-java-nested-types.check
@@ -0,0 +1,21 @@
+-- [E007] Type Mismatch Error: tests/neg/i24711-java-nested-types.scala:2:20 -------------------------------------------
+2 |  val test1: Int = (??? : java.util.Map.Entry[String, Int])  // error
+  |                    ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+  |                    Found:    java.util.Map.Entry[String, Int]
+  |                    Required: Int
+  |
+  | longer explanation available when compiling with `-explain`
+-- [E007] Type Mismatch Error: tests/neg/i24711-java-nested-types.scala:4:38 -------------------------------------------
+4 |  val test2: Int = java.util.Map.entry("key", 1)  // error
+  |                   ^^^^^^^^^^^^^^^^^^^^^^^^^^^^^
+  |                   Found:    java.util.Map.Entry[String, Int]
+  |                   Required: Int
+  |
+  | longer explanation available when compiling with `-explain`
+-- [E007] Type Mismatch Error: tests/neg/i24711-java-nested-types.scala:7:20 -------------------------------------------
+7 |  val test4: Int = (??? : Outer#Inner)  // error
+  |                    ^^^^^^^^^^^^^^^^^
+  |                    Found:    Test.this.Outer#Inner
+  |                    Required: Int
+  |
+  | longer explanation available when compiling with `-explain`
diff --git a/tests/neg/i24711-java-nested-types.scala b/tests/neg/i24711-java-nested-types.scala
new file mode 100644
index 000000000000..bb27a15df245
--- /dev/null
+++ b/tests/neg/i24711-java-nested-types.scala
@@ -0,0 +1,8 @@
+class Test {
+  val test1: Int = (??? : java.util.Map.Entry[String, Int])  // error
+
+  val test2: Int = java.util.Map.entry("key", 1)  // error
+
+  trait Outer { type Inner }
+  val test4: Int = (??? : Outer#Inner)  // error
+}