diff --git a/test/hotspot/jtreg/serviceability/sa/TestJmapCoreMetaspace.java b/test/hotspot/jtreg/serviceability/sa/TestJmapCoreMetaspace.java
index 3dd060be231..b8e00e53848 100644
--- a/test/hotspot/jtreg/serviceability/sa/TestJmapCoreMetaspace.java
+++ b/test/hotspot/jtreg/serviceability/sa/TestJmapCoreMetaspace.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2018, 2020, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 2018, 2023, 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
@@ -23,7 +23,7 @@
 
 /**
  * @test TestJmapCoreMetaspace
- * @summary Test verifies that jhsdb jmap could generate heap dump from core when metspace is full
+ * @summary Test verifies that jhsdb jmap could generate heap dump from core when metaspace is full
  * @requires vm.hasSA
  * @library /test/lib
  * @run driver/timeout=480 TestJmapCore run metaspace
diff --git a/test/lib-test/jdk/test/lib/TestMutuallyExclusivePlatformPredicates.java b/test/lib-test/jdk/test/lib/TestMutuallyExclusivePlatformPredicates.java
index 045be5361d7..355cd8ac200 100644
--- a/test/lib-test/jdk/test/lib/TestMutuallyExclusivePlatformPredicates.java
+++ b/test/lib-test/jdk/test/lib/TestMutuallyExclusivePlatformPredicates.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2014, 2022, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 2014, 2023, 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
@@ -53,7 +53,7 @@ public class TestMutuallyExclusivePlatformPredicates {
         IGNORED("isEmulatedClient", "isDebugBuild", "isFastDebugBuild", "isMusl",
                 "isSlowDebugBuild", "hasSA", "isRoot", "isTieredSupported",
                 "areCustomLoadersSupportedForCDS", "isDefaultCDSArchiveSupported",
-                "isHardenedOSX");
+                "isHardenedOSX", "hasOSXPlistEntries");
 
         public final List<String> methodNames;
 
diff --git a/test/lib/jdk/test/lib/Platform.java b/test/lib/jdk/test/lib/Platform.java
index 647c62834aa..c58877c6c5e 100644
--- a/test/lib/jdk/test/lib/Platform.java
+++ b/test/lib/jdk/test/lib/Platform.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2013, 2022, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 2013, 2023, 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
@@ -260,6 +260,36 @@ public class Platform {
         return true;
     }
 
+    private static Process launchCodesignOnJavaBinary() throws IOException {
+        String jdkPath = System.getProperty("java.home");
+        Path javaPath = Paths.get(jdkPath + "/bin/java");
+        String javaFileName = javaPath.toAbsolutePath().toString();
+        if (Files.notExists(javaPath)) {
+            throw new FileNotFoundException("Could not find file " + javaFileName);
+        }
+        ProcessBuilder pb = new ProcessBuilder("codesign", "--display", "--verbose", javaFileName);
+        pb.redirectErrorStream(true); // redirect stderr to stdout
+        Process codesignProcess = pb.start();
+        return codesignProcess;
+    }
+
+    public static boolean hasOSXPlistEntries() throws IOException {
+        Process codesignProcess = launchCodesignOnJavaBinary();
+        BufferedReader is = new BufferedReader(new InputStreamReader(codesignProcess.getInputStream()));
+        String line;
+        while ((line = is.readLine()) != null) {
+            System.out.println("STDOUT: " + line);
+            if (line.indexOf("Info.plist=not bound") != -1) {
+                return false;
+            }
+            if (line.indexOf("Info.plist entries=") != -1) {
+                return true;
+            }
+        }
+        System.out.println("No matching Info.plist entry was found");
+        return false;
+    }
+
     /**
      * Return true if the test JDK is hardened, otherwise false. Only valid on OSX.
      */
@@ -269,19 +299,7 @@ public class Platform {
         if (getOsVersionMajor() == 10 && getOsVersionMinor() < 14) {
             return false; // assume not hardened
         }
-
-        // Find the path to the java binary.
-        String jdkPath = System.getProperty("java.home");
-        Path javaPath = Paths.get(jdkPath + "/bin/java");
-        String javaFileName = javaPath.toAbsolutePath().toString();
-        if (Files.notExists(javaPath)) {
-            throw new FileNotFoundException("Could not find file " + javaFileName);
-        }
-
-        // Run codesign on the java binary.
-        ProcessBuilder pb = new ProcessBuilder("codesign", "--display", "--verbose", javaFileName);
-        pb.redirectErrorStream(true); // redirect stderr to stdout
-        Process codesignProcess = pb.start();
+        Process codesignProcess = launchCodesignOnJavaBinary();
         BufferedReader is = new BufferedReader(new InputStreamReader(codesignProcess.getInputStream()));
         String line;
         boolean isHardened = false;
diff --git a/test/lib/jdk/test/lib/util/CoreUtils.java b/test/lib/jdk/test/lib/util/CoreUtils.java
index f69ef5ce08e..f7a486def2b 100644
--- a/test/lib/jdk/test/lib/util/CoreUtils.java
+++ b/test/lib/jdk/test/lib/util/CoreUtils.java
@@ -1,5 +1,5 @@
 /*
- * Copyright (c) 2020, 2022, Oracle and/or its affiliates. All rights reserved.
+ * Copyright (c) 2020, 2023, 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
@@ -127,6 +127,8 @@ public class CoreUtils {
             }
 
             return coreFileLocation; // success!
+        } else {
+            System.out.println("Core file not found. Trying to find a reason why...");
         }
 
         // See if we can figure out the likely reason the core file was not found. Recover from
@@ -148,6 +150,11 @@ public class CoreUtils {
                     // We can't generate cores files with hardened binaries on OSX 10.15 and later.
                     throw new SkippedException("Cannot produce core file with hardened binary on OSX 10.15 and later");
                 }
+            } else {
+                // codesign has to add entitlements using the plist. If this is not present we might not generate a core file.
+                if (!Platform.hasOSXPlistEntries()) {
+                    throw new SkippedException("Cannot produce core file with binary having no plist entitlement entries");
+                }
             }
         } else if (Platform.isLinux()) {
             // Check if a crash report tool is installed.