--- a/src/hotspot/share/prims/jvmtiRedefineClasses.cpp	Mon Jul 29 11:14:06 2019 +0200
+++ b/src/hotspot/share/prims/jvmtiRedefineClasses.cpp	Mon Jul 29 09:57:37 2019 -0400
@@ -1623,6 +1623,11 @@
     return JVMTI_ERROR_INTERNAL;
   }
 
+  if (old_cp->has_dynamic_constant()) {
+    merge_cp->set_has_dynamic_constant();
+    scratch_cp->set_has_dynamic_constant();
+  }
+
   log_info(redefine, class, constantpool)("merge_cp_len=%d, index_map_len=%d", merge_cp_length, _index_map_count);
 
   if (_index_map_count == 0) {
@@ -3246,6 +3251,10 @@
   // reference to the cp holder is needed for copy_operands()
   smaller_cp->set_pool_holder(scratch_class);
 
+  if (scratch_cp->has_dynamic_constant()) {
+    smaller_cp->set_has_dynamic_constant();
+  }
+
   scratch_cp->copy_cp_to(1, scratch_cp_length - 1, smaller_cp, 1, THREAD);
   if (HAS_PENDING_EXCEPTION) {
     // Exception is handled in the caller

--- /dev/null	Thu Jan 01 00:00:00 1970 +0000
+++ b/test/hotspot/jtreg/serviceability/jvmti/RedefineClasses/RedefineCondy.jasm	Mon Jul 29 09:57:37 2019 -0400
@@ -0,0 +1,43 @@
+/*
+ * Copyright (c) 2019, Oracle and/or its affiliates. All rights reserved.
+ * DO NOT ALTER OR REMOVE COPYRIGHT NOTICES OR THIS FILE HEADER.
+ *
+ * This code is free software; you can redistribute it and/or modify it
+ * under the terms of the GNU General Public License version 2 only, as
+ * published by the Free Software Foundation.
+ *
+ * This code is distributed in the hope that it will be useful, but WITHOUT
+ * ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or
+ * FITNESS FOR A PARTICULAR PURPOSE.  See the GNU General Public License
+ * version 2 for more details (a copy is included in the LICENSE file that
+ * accompanied this code).
+ *
+ * You should have received a copy of the GNU General Public License version
+ * 2 along with this work; if not, write to the Free Software Foundation,
+ * Inc., 51 Franklin St, Fifth Floor, Boston, MA 02110-1301 USA.
+ *
+ * Please contact Oracle, 500 Oracle Parkway, Redwood Shores, CA 94065 USA
+ * or visit www.oracle.com if you need additional information or have any
+ * questions.
+ */
+
+super public class RedefineCondy version 55:0 {
+
+    public Method "<init>":"(Ljava/lang/invoke/MethodHandles$Lookup;Ljava/lang/String;Ljava/lang/Class;)V"
+    stack 3 locals 4 {
+        aload_0;
+        invokespecial   Method java/lang/Object."<init>":"()V";
+        getstatic       Field java/lang/System.out:"Ljava/io/PrintStream;";
+        ldc             String "In RedefineCondy <init> method";
+        invokevirtual   Method java/io/PrintStream.println:"(Ljava/lang/String;)V";
+        return;
+    }
+
+    public static Method main:"([Ljava/lang/String;)V" stack 3 locals 1 {
+        new    class RedefineCondy;
+        dup;
+        ldc    Dynamic REF_newInvokeSpecial:RedefineCondy."<init>":"(Ljava/lang/invoke/MethodHandles$Lookup;Ljava/lang/String;Ljava/lang/Class;)V":RedefineCondy:"Ljava/lang/Object;";
+        return;
+    }
+
+} // end Class RedefineCondy

--- /dev/null	Thu Jan 01 00:00:00 1970 +0000
+++ b/test/hotspot/jtreg/serviceability/jvmti/RedefineClasses/TestRedefineCondy.java	Mon Jul 29 09:57:37 2019 -0400
@@ -0,0 +1,60 @@
+/*
+ * Copyright (c) 2019, Oracle and/or its affiliates. All rights reserved.
+ * DO NOT ALTER OR REMOVE COPYRIGHT NOTICES OR THIS FILE HEADER.
+ *
+ * This code is free software; you can redistribute it and/or modify it
+ * under the terms of the GNU General Public License version 2 only, as
+ * published by the Free Software Foundation.
+ *
+ * This code is distributed in the hope that it will be useful, but WITHOUT
+ * ANY WARRANTY; without even the implied warranty of MERCHANTABILITY or
+ * FITNESS FOR A PARTICULAR PURPOSE.  See the GNU General Public License
+ * version 2 for more details (a copy is included in the LICENSE file that
+ * accompanied this code).
+ *
+ * You should have received a copy of the GNU General Public License version
+ * 2 along with this work; if not, write to the Free Software Foundation,
+ * Inc., 51 Franklin St, Fifth Floor, Boston, MA 02110-1301 USA.
+ *
+ * Please contact Oracle, 500 Oracle Parkway, Redwood Shores, CA 94065 USA
+ * or visit www.oracle.com if you need additional information or have any
+ * questions.
+ */
+
+/*
+ * @test
+ * @bug 8228596
+ * @summary Test redefining a class with a condy in its constant pool
+ * @library /test/lib
+ * @modules java.base/jdk.internal.misc
+ * @modules java.compiler
+ *          java.instrument
+ *          jdk.jartool/sun.tools.jar
+ * @compile RedefineCondy.jasm
+ * @run main RedefineClassHelper
+ * @run main/othervm -javaagent:redefineagent.jar TestRedefineCondy
+ */
+
+import jdk.test.lib.compiler.InMemoryJavaCompiler;
+
+// Test redefining a class that has a constant dynamic in its constant pool
+// to a class that does not have a constant dynamic in its constant pool.
+public class TestRedefineCondy {
+
+    static final String DEST = System.getProperty("test.classes");
+    static String newClass =
+        "public class RedefineCondy { " +
+        "public RedefineCondy(java.lang.invoke.MethodHandles.Lookup l, java.lang.String s, java.lang.Class c) { } " +
+    "public static void main(String argv[]) { } } ";
+
+    public static void main(String[] args) throws Exception  {
+        Class<?> classWithCondy = Class.forName("RedefineCondy");
+
+        try {
+            byte[] classBytes = InMemoryJavaCompiler.compile("RedefineCondy", newClass);
+            RedefineClassHelper.redefineClass(classWithCondy, classBytes);
+        } catch (Exception e) {
+            throw new RuntimeException("Unexpected exception: " + e.getMessage());
+        }
+    }
+}