diff --git a/src/Tasks/ManifestUtil/mansign2.cs b/src/Tasks/ManifestUtil/mansign2.cs
index da2308866d1..dfc7d8e46c2 100644
--- a/src/Tasks/ManifestUtil/mansign2.cs
+++ b/src/Tasks/ManifestUtil/mansign2.cs
@@ -814,13 +814,28 @@ private static string ObtainRFC3161Timestamp(string timeStampUrl, string signatu
 
                 try
                 {
-                    byte[] nonce = new byte[24];
+                    byte[] nonce = new byte[32];
 
                     using (RandomNumberGenerator rng = RandomNumberGenerator.Create())
                     {
                         rng.GetBytes(nonce);
                     }
 
+                    // Eventually, CryptEncodeObjectEx(...) is called on a CRYPT_TIMESTAMP_REQUEST with this nonce,
+                    // and CryptEncodeObjectEx(...) interprets the nonce as a little endian, DER-encoded integer value
+                    // (without tag and length), and may even strip leading bytes from the big endian representation
+                    // of the byte sequence to achieve proper integer DER encoding.
+                    //
+                    // If the nonce is changed after the client generates it, the timestamp server would receive
+                    // and return a nonce that does not agree with the client's original nonce.
+                    //
+                    // To ensure this does not happen, ensure that the most significant byte in the little
+                    // endian byte sequence is in the 0x01-0x7F range; clear that byte's most significant bit
+                    // and set that byte's least significant bit.
+ 
+                    nonce[nonce.Length - 1] &= 0x7f;
+                    nonce[nonce.Length - 1] |= 0x01;
+
                     Win32.CRYPT_TIMESTAMP_PARA para = new Win32.CRYPT_TIMESTAMP_PARA()
                     {
                         fRequestCerts = true,