diff --git a/WHATSNEW b/WHATSNEW
index b34197e39..b950a35bc 100644
--- a/WHATSNEW
+++ b/WHATSNEW
@@ -9,6 +9,12 @@ Fixed bugs:
    an exception.
    Bugzilla Report 62499
 
+ * the new allowFilesToEscapeDest didn't work when set to false and
+   archive entries contained relative paths with so many ".."
+   segnments that the resulting path would go beyond the file system
+   root.
+   Bugzilla Report 62502
+
 Changes from Ant 1.10.3 TO Ant 1.10.4
 =====================================
 
diff --git a/src/main/org/apache/tools/ant/taskdefs/Expand.java b/src/main/org/apache/tools/ant/taskdefs/Expand.java
index 3b62ea820..b526a78de 100644
--- a/src/main/org/apache/tools/ant/taskdefs/Expand.java
+++ b/src/main/org/apache/tools/ant/taskdefs/Expand.java
@@ -332,9 +332,9 @@ public class Expand extends Task {
             mappedNames = new String[] {entryName};
         }
         File f = fileUtils.resolveFile(dir, mappedNames[0]);
-        if (!allowedOutsideOfDest && !fileUtils.isLeadingPath(dir, f)) {
-            log("skipping " + entryName + " as its target " + f + " is outside of "
-                + dir + ".", Project.MSG_VERBOSE);
+        if (!allowedOutsideOfDest && !fileUtils.isLeadingPath(dir, f, true)) {
+            log("skipping " + entryName + " as its target " + f.getCanonicalPath()
+                + " is outside of " + dir.getCanonicalPath() + ".", Project.MSG_VERBOSE);
                 return;
         }
 
diff --git a/src/main/org/apache/tools/ant/util/FileUtils.java b/src/main/org/apache/tools/ant/util/FileUtils.java
index 864db5e5b..34b5d9d0d 100644
--- a/src/main/org/apache/tools/ant/util/FileUtils.java
+++ b/src/main/org/apache/tools/ant/util/FileUtils.java
@@ -729,8 +729,12 @@ public class FileUtils {
      *   <li>DOS style paths that start with a drive letter will have
      *     \ as the separator.</li>
      * </ul>
-     * Unlike {@link File#getCanonicalPath()} this method
-     * specifically does not resolve symbolic links.
+     * <p>Unlike {@link File#getCanonicalPath()} this method
+     * specifically does not resolve symbolic links.</p>
+     *
+     * <p>If the path tries to go beyond the file system root (i.e. it
+     * contains more ".." segments than can be travelled up) the
+     * method will return the original path unchanged.</p>
      *
      * @param path the path to be normalized.
      * @return the normalized version of the path.
@@ -1155,6 +1159,9 @@ public class FileUtils {
     /**
      * Removes a leading path from a second path.
      *
+     * <p>This method uses {@link #normalize} under the covers and
+     * does not resolve symbolic links.</p>
+     *
      * @param leading The leading path, must not be null, must be absolute.
      * @param path The path to remove from, must not be null, must be absolute.
      *
@@ -1179,8 +1186,16 @@ public class FileUtils {
 
     /**
      * Learn whether one path "leads" another.
+     *
+     * <p>This method uses {@link #normalize} under the covers and
+     * does not resolve symbolic links.</p>
+     *
+     * <p>If either path tries to go beyond the file system root
+     * (i.e. it contains more ".." segments than can be travelled up)
+     * the method will return false.</p>
+     *
      * @param leading The leading path, must not be null, must be absolute.
-     * @param path The path to remove from, must not be null, must be absolute.
+     * @param path The path to check, must not be null, must be absolute.
      * @return true if path starts with leading; false otherwise.
      * @since Ant 1.7
      */
@@ -1195,6 +1210,41 @@ public class FileUtils {
         if (!l.endsWith(File.separator)) {
             l += File.separator;
         }
+        // ensure "/foo/"  is not considered a parent of "/foo/../../bar"
+        String up = File.separator + ".." + File.separator;
+        if (l.contains(up) || p.contains(up) || (p + File.separator).contains(up)) {
+            return false;
+        }
+        return p.startsWith(l);
+    }
+
+    /**
+     * Learn whether one path "leads" another.
+     *
+     * @param leading The leading path, must not be null, must be absolute.
+     * @param path The path to check, must not be null, must be absolute.
+     * @param resolveSymlinks whether symbolic links shall be resolved
+     * prior to comparing the paths.
+     * @return true if path starts with leading; false otherwise.
+     * @since Ant 1.10.5
+     * @throws IOException if resolveSymlinks is true and invoking
+     * getCanonicaPath on either argument throws an exception
+     */
+    public boolean isLeadingPath(File leading, File path, boolean resolveSymlinks)
+        throws IOException {
+        if (!resolveSymlinks) {
+            return isLeadingPath(leading, path);
+        }
+        String l = leading.getCanonicalPath();
+        String p = path.getCanonicalPath();
+        if (l.equals(p)) {
+            return true;
+        }
+        // ensure that l ends with a /
+        // so we never think /foo was a parent directory of /foobar
+        if (!l.endsWith(File.separator)) {
+            l += File.separator;
+        }
         return p.startsWith(l);
     }
 
diff --git a/src/tests/junit/org/apache/tools/ant/util/FileUtilsTest.java b/src/tests/junit/org/apache/tools/ant/util/FileUtilsTest.java
index cdd68e148..b7d34457d 100644
--- a/src/tests/junit/org/apache/tools/ant/util/FileUtilsTest.java
+++ b/src/tests/junit/org/apache/tools/ant/util/FileUtilsTest.java
@@ -601,11 +601,53 @@ public class FileUtilsTest {
         }
 
     }
+
+    @Test
     public void testGetDefaultEncoding() {
         // This just tests that the function does not blow up
         FILE_UTILS.getDefaultEncoding();
     }
 
+    /**
+     * @see "https://bz.apache.org/bugzilla/show_bug.cgi?id=62502"
+     */
+    @Test
+    public void isLeadingPathCannotBeFooledByTooManyDoubleDots() {
+        assertFalse(FILE_UTILS.isLeadingPath(new File("/foo"), new File("/foo/../../bar")));
+        assertFalse(FILE_UTILS.isLeadingPath(new File("c:\\foo"), new File("c:\\foo\\..\\..\\bar")));
+        assertFalse(FILE_UTILS.isLeadingPath(new File("/foo"), new File("/foo/../..")));
+    }
+
+    /**
+     * @see "https://bz.apache.org/bugzilla/show_bug.cgi?id=62502"
+     */
+    @Test
+    public void isLeadingPathCanonicalVersionCannotBeFooledByTooManyDoubleDots() throws IOException {
+        assertFalse(FILE_UTILS.isLeadingPath(new File("/foo"), new File("/foo/../../bar"), true));
+        assertFalse(FILE_UTILS.isLeadingPath(new File("c:\\foo"), new File("c:\\foo\\..\\..\\bar"), true));
+        assertFalse(FILE_UTILS.isLeadingPath(new File("/foo"), new File("/foo/../.."), true));
+    }
+
+    @Test
+    public void isLeadingPathCanonicalVersionWorksAsExpectedOnUnix() throws IOException {
+        assumeFalse("Test doesn't run on DOS", Os.isFamily("dos"));
+        assertTrue(FILE_UTILS.isLeadingPath(new File("/foo"), new File("/foo/bar"), true));
+        assertTrue(FILE_UTILS.isLeadingPath(new File("/foo"), new File("/foo/baz/../bar"), true));
+        assertTrue(FILE_UTILS.isLeadingPath(new File("/foo"), new File("/foo/../foo/bar"), true));
+        assertFalse(FILE_UTILS.isLeadingPath(new File("/foo"), new File("/foobar"), true));
+        assertFalse(FILE_UTILS.isLeadingPath(new File("/foo"), new File("/bar"), true));
+    }
+
+    @Test
+    public void isLeadingPathCanonicalVersionWorksAsExpectedOnDos() throws IOException {
+        assumeTrue("Test only runs on DOS", Os.isFamily("dos"));
+        assertTrue(FILE_UTILS.isLeadingPath(new File("C:\\foo"), new File("C:\\foo\\bar"), true));
+        assertTrue(FILE_UTILS.isLeadingPath(new File("C:\\foo"), new File("C:\\foo\\baz\\..\\bar"), true));
+        assertTrue(FILE_UTILS.isLeadingPath(new File("C:\\foo"), new File("C:\\foo\\..\\foo\\bar"), true));
+        assertFalse(FILE_UTILS.isLeadingPath(new File("C:\\foo"), new File("C:\\foobar"), true));
+        assertFalse(FILE_UTILS.isLeadingPath(new File("C:\\foo"), new File("C:\\bar"), true));
+    }
+
     /**
      * adapt file separators to local conventions
      */