diff --git a/WHATSNEW b/WHATSNEW
index 5b2bff393..919ca9b90 100644
--- a/WHATSNEW
+++ b/WHATSNEW
@@ -21,8 +21,6 @@ Fixed bugs:
 
 * AntLikeTasksAtTopLevelTest failed on cygwin.
 
-* <junit> and <assertions> are working together. Bugzilla report 27218
-
 * I/O-intensive processes hung when executed via <exec spawn="true">.
   Bugzilla reports 23893/26852.
 
@@ -119,6 +117,8 @@ Fixed bugs:
 * <zip> and friends would delete the original file when trying to update
   a read-only archive.  Bugzilla Report 28419.
 
+* <junit> and <assertions> are working together. Bugzilla report 27218
+
 Other changes:
 --------------
 
diff --git a/src/main/org/apache/tools/ant/types/Assertions.java b/src/main/org/apache/tools/ant/types/Assertions.java
index ee5824f7d..51c18d9da 100644
--- a/src/main/org/apache/tools/ant/types/Assertions.java
+++ b/src/main/org/apache/tools/ant/types/Assertions.java
@@ -20,9 +20,10 @@ package org.apache.tools.ant.types;
 import org.apache.tools.ant.BuildException;
 import org.apache.tools.ant.Project;
 
-import java.util.List;
 import java.util.ArrayList;
 import java.util.Iterator;
+import java.util.List;
+import java.util.ListIterator;
 
 /**
  * The assertion datatype. This type describes
@@ -202,6 +203,33 @@ public class Assertions extends DataType implements Cloneable {
         }
     }
 
+    /**
+     * add the assertions to a list in a format suitable
+     * for adding to a command line
+     * @param commandList
+     */
+    public void applyAssertions(final ListIterator commandIterator) {
+        getProject().log("Applying assertions", Project.MSG_DEBUG);
+        Assertions clause = getFinalReference();
+        //do the system assertions
+        if (Boolean.TRUE.equals(clause.enableSystemAssertions)) {
+            getProject().log("Enabling system assertions", Project.MSG_DEBUG);
+            commandIterator.add("-enablesystemassertions");
+        } else if (Boolean.FALSE.equals(clause.enableSystemAssertions)) {
+            getProject().log("disabling system assertions", Project.MSG_DEBUG);
+            commandIterator.add("-disablesystemassertions");
+        }
+
+        //now any inner assertions
+        Iterator it = clause.assertionList.iterator();
+        while (it.hasNext()) {
+            BaseAssertion assertion = (BaseAssertion) it.next();
+            String arg = assertion.toCommand();
+            getProject().log("adding assertion "+arg, Project.MSG_DEBUG);
+            commandIterator.add(arg);
+        }
+    }
+
     /**
      * helper method to add a string JVM argument to a command
      * @param command
diff --git a/src/main/org/apache/tools/ant/types/CommandlineJava.java b/src/main/org/apache/tools/ant/types/CommandlineJava.java
index 772653082..37b683f8e 100644
--- a/src/main/org/apache/tools/ant/types/CommandlineJava.java
+++ b/src/main/org/apache/tools/ant/types/CommandlineJava.java
@@ -401,7 +401,7 @@ public class CommandlineJava implements Cloneable {
 
         //now any assertions are added
         if (getAssertions() != null) {
-            getAssertions().applyAssertions(this);
+            getAssertions().applyAssertions(listIterator);
         }
 
         // JDK usage command line says that -jar must be the first option, as there is
diff --git a/src/testcases/org/apache/tools/ant/types/CommandlineJavaTest.java b/src/testcases/org/apache/tools/ant/types/CommandlineJavaTest.java
index 3caf70e66..848c2bac6 100644
--- a/src/testcases/org/apache/tools/ant/types/CommandlineJavaTest.java
+++ b/src/testcases/org/apache/tools/ant/types/CommandlineJavaTest.java
@@ -18,6 +18,7 @@
 package org.apache.tools.ant.types;
 
 import org.apache.tools.ant.Project;
+import org.apache.tools.ant.util.JavaEnvUtils;
 
 import junit.framework.TestCase;
 import junit.framework.AssertionFailedError;
@@ -142,4 +143,45 @@ public class CommandlineJavaTest extends TestCase {
         assertNull(System.getProperty("key2"));
     }
 
+    public void testAssertions() {
+        if (JavaEnvUtils.isJavaVersion(JavaEnvUtils.JAVA_1_2)
+            || JavaEnvUtils.isJavaVersion(JavaEnvUtils.JAVA_1_3)) {
+            return;
+        }
+
+        CommandlineJava c = new CommandlineJava();
+        c.createArgument().setValue("org.apache.tools.ant.CommandlineJavaTest");
+        c.setClassname("junit.textui.TestRunner");
+        c.createVmArgument().setValue("-Djava.compiler=NONE");
+        Assertions a = new Assertions();
+        a.setProject(project);
+        Assertions.EnabledAssertion ea = new Assertions.EnabledAssertion();
+        ea.setClass("junit.textui.TestRunner");
+        a.addEnable(ea);
+        c.setAssertions(a);
+
+        String[] expected = new String[] {
+            null,
+            "-Djava.compiler=NONE",
+            "-ea:junit.textui.TestRunner",
+            "junit.textui.TestRunner",
+            "org.apache.tools.ant.CommandlineJavaTest",
+        };
+            
+        // only the second iteration would pass because of PR 27218
+        for (int i = 0; i < 3; i++) {
+            String[] s = c.getCommandline();
+            assertEquals(expected.length, s.length);
+            for (int j = 1; j < expected.length; j++) {
+                assertEquals(expected[j], s[j]);
+            }
+        }
+        CommandlineJava c2 = (CommandlineJava) c.clone();
+        String[] s = c2.getCommandline();
+        assertEquals(expected.length, s.length);
+        for (int j = 1; j < expected.length; j++) {
+            assertEquals(expected[j], s[j]);
+        }
+    }
+
 }