diff --git a/WHATSNEW b/WHATSNEW
index a55eed50f..1bc965607 100644
--- a/WHATSNEW
+++ b/WHATSNEW
@@ -325,6 +325,9 @@ Fixed bugs:
 * <zip>'s defaultexcludes attribute was ignored when an archive was
   updated.  Bugzilla Report 33412.
 
+* <zip> couldn't store files with size between 2GB and 4GB (the
+  upper limit set by the ZIP format itself).  Bugzilla Report 33310.
+
 Changes from Ant 1.6.1 to Ant 1.6.2
 ===================================
 
diff --git a/src/main/org/apache/tools/zip/ZipOutputStream.java b/src/main/org/apache/tools/zip/ZipOutputStream.java
index c2d9926de..2db125136 100644
--- a/src/main/org/apache/tools/zip/ZipOutputStream.java
+++ b/src/main/org/apache/tools/zip/ZipOutputStream.java
@@ -336,8 +336,8 @@ public class ZipOutputStream extends FilterOutputStream {
                 deflate();
             }
 
-            entry.setSize(def.getTotalIn());
-            entry.setComprSize(def.getTotalOut());
+            entry.setSize(adjustToLong(def.getTotalIn()));
+            entry.setComprSize(adjustToLong(def.getTotalOut()));
             entry.setCrc(realCrc);
 
             def.reset();
@@ -877,4 +877,19 @@ public class ZipOutputStream extends FilterOutputStream {
             out.write(data, offset, length);
         }
     }
+
+    /**
+     * Assumes a negative integer really is a positive integer that
+     * has wrapped around and re-creates the original value.
+     *
+     * @since 1.34
+     */
+    protected static long adjustToLong(int i) {
+        if (i < 0) {
+            return 2 * ((long) Integer.MAX_VALUE) + 2 + i;
+        } else {
+            return i;
+        }
+    }
+
 }
diff --git a/src/testcases/org/apache/tools/zip/ZipOutputStreamTest.java b/src/testcases/org/apache/tools/zip/ZipOutputStreamTest.java
index fa92f858e..3fc45555a 100644
--- a/src/testcases/org/apache/tools/zip/ZipOutputStreamTest.java
+++ b/src/testcases/org/apache/tools/zip/ZipOutputStreamTest.java
@@ -1,5 +1,5 @@
 /*
- * Copyright 2004 The Apache Software Foundation
+ * Copyright 2004-2005 The Apache Software Foundation
  *
  *  Licensed under the Apache License, Version 2.0 (the "License");
  *  you may not use this file except in compliance with the License.
@@ -66,4 +66,13 @@ public class ZipOutputStreamTest extends TestCase {
         assertEquals(test.getValue(), zl.getValue());
     }
 
+    public void testAdjustToLong() {
+        assertEquals((long) Integer.MAX_VALUE,
+                     ZipOutputStream.adjustToLong(Integer.MAX_VALUE));
+        assertEquals(((long) Integer.MAX_VALUE) + 1,
+                     ZipOutputStream.adjustToLong(Integer.MAX_VALUE + 1));
+        assertEquals(2 * ((long) Integer.MAX_VALUE),
+                     ZipOutputStream.adjustToLong(2 * Integer.MAX_VALUE));
+    }
+
 }