[Esapi-user] [Esapi-dev] Why ESAPI crypto uses a custom serialization scheme

Jim Manico jim.manico at owasp.org
Sat May 1 02:31:05 EDT 2010

I agree with Jeff - this is an epic email from Kevin.

My actual hands-on-coding mentorship and participation has been poor  
lately -but I do commit to keep up with the buildmaster duties when  
the need arises.

I'm stoked to see more activity - I can just feel the 2.0 GA release  
getting closer.

And after 2.0 is live - I have a big charge (and developer support) to  
re-write the encoder architecture in a much much more high performance  

Anyhow - thanks all - and let me know when you have that proposal to  
hire a crypto-pro review/assessment candidate(s). :)

Jim Manico

On Apr 30, 2010, at 2:03 PM, "Kevin W. Wall" <kevin.w.wall at gmail.com>  

> As promised... (Or should that be, "as threatened?" ;-)
> In another thread (Call for review of crypto code), Mike Boberski
> asked why I chose a custom serialization scheme rather than something
> like CMS or PKCS#7.
> Great question. (WARNING: If you fall asleep easily at boring  
> technical
> details, you may want to grab a cup of coffee.  OTOH, if you are
> suffering from insomnia, read on. :)
> First, let me say, I never really seriously considered using PKCS#7.
> CMS (Cryptographic Message Syntax, RFC 5652) is derived from the
> latest version of PKCS#7 (v1.5), and since that time there have been
> 3 or 4 revisions of CMS.  So for the most part PKCS#7 has been  
> superceded
> by CMS.
> Secondly, let me state my reason and the design goals for some
> serialization scheme, whether that be CMS or JSON or XML Encrypt
> or some other custom serialization scheme.
>  Reason:
>    We needed a _portable_ way to transport ciphertext over an
>    insecure communications channel that was independent of OS
>    or hardware architecture but that would not only allow the
>    recipient to decrypt it, but also allow the recipient to
>    detect whether or not an adversary had tampered with the
>    data stream. (Recall the assumption was that this might
>    not be transported over a secure channel.)
>  Design Goals:
>    1)  Portable across different hardware architectures (e.g.,
>        big-endian vs. little-endian issues)
>    2)  Portable across programming languages. Should be independent
>        of size of 'int' types, whether integers are signed or  
> unsigned,
>        etc.
>    3)  Should have libraries available (preferably native to the
>        programming language) or should be easy to build in all that
>        is required to support it for all programming languages that
>        ESAPI supports. Where such libraries already exist, they should
>        be fairly easy to use.
>    4)  Should be able to be "self-contained" in that it should store
>        everything that is needed to decrypt it except for the  
> encryption
>        key itself. This would include the cipher algorithm, the cipher
>        mode, the padding scheme, the IV, and a MAC to ensure  
> authenticity.
>    5)  Representation of the encrypted serialized data should be  
> compact
>        as possible. (At Qwest, there was a *lot* of pushback from
>        development teams when they discovered that SSN or CC#s took
>        more space to store when encrypted than as plaintext. Most of  
> this
>        is because of the padding scheme and IV, but that didn't  
> matter.)
>    6)  There should be minimal additional processing overhead in
>        interacting with this encrypted serialized data. Keep in mind  
> there
>        are applications where they may encrypt / decrypt several  
> million
>        data items in a tight loop during some batch processing so
>    7)  Should be extensible and the extensibility should be able to  
> support
>        backward compatibility with earlier versions.
> As I started looking into seeing if I could use CMS for this I  
> realized
> a couple of things.
>    a) CMS / PKCS#7 are much more complicated than what we needed. It  
> does
>       much more than to encrypt arbitrary message content.. It can  
> also
>       be used to support digital signatures, digests, authenticate.,  
> etc.
>       There have been 3 or 4 revisions of the RFC for this,  
> depending on how
>       you count. That complexity makes it hard to implement  
> correctly and
>       it would likely result in incompatibility across different  
> versions
>       of CMS.
>    b) I did not find it widely implemented. In Java, the SunJCE has  
> support
>       for portions of CMS, but they do not have any explicity java.*  
> or
>       javax.* CMS related classes. (There may be some com.sun.*  
> classes
>       to support it, but using those directly is probably best avoided
>       anyway.) I believe that Bouncy Castle has more generic support  
> for
>       CMS, but we felt that we did not want to rely on any  
> particular JCE
>       provider as most folks will just wish to stick with SunJCE.
>    c) After thinking about all the programming languages that ESAPI is
>       in the works to support (Java, .NET, PHP, classic ASP,  
> ColdFusion/CFML,
>       Python, Haskell, and whatever language is used on  
> SalesForce.com;
>       note: JavaScript not included because in general, it would be  
> absurd
>       to encrypt on the client side in almost all cases), I realized  
> that
>       something as complex as CMS would never be implemented on all  
> these
>       languages. But because CMS is so complex (compared to the custom
>       serialization scheme that I chose), it would be much harder to
>       implement ESAPI encryption so we could build it in such a  
> manner that
>       was interoperable across all the ESAPI versions. In fact,  
> implementing
>       CMS in a language where you do not have an ASN.1 parser  
> available
>       would make it very difficult to implement straight from the RFC.
>       BER and DER encoding is used throughout CMS. There quite  
> likely is
>       some FOSS version of CMS for Java and I think that .NET has at  
> least
>       partial support for CMS, but implementing this for PHP, Python,
>       Haskell, etc. would take quite a major effort.
>    d) In addition to CMS, I also (very briefly) considered XML  
> Encrypt for
>       serialization. It is a much simpler standard and likely has  
> broader
>       implementation support than does CMS, but it's big problem is  
> that
>       its resulting size is huge by comparison to other possible
>       serialization schemes.
> So instead, last October, I sought out advice of cryptographers on the
> cryptography mailing list on Metzdowd.com. And one cryptographer,
> Ian Griggs, responded by point me at some similar work that he had  
> done.
> That became the inspiration for the current custom serialization  
> scheme
> we are using today.  While that serialization scheme is not  
> implemented
> on any other programming language of ESAPI today, I do believe that it
> is simple enough to implement practically anywhere.
> Finally, the use of this current custom serialization scheme does not
> preclude the use of CMS or XML Encrypt or anything else.
> If anyone has any other specific questions about this, I'll try to
> answer them as best I can.
> OK, time to wake up now!!!
> -kevin
> -- 
> Kevin W. Wall
> "The most likely way for the world to be destroyed, most experts  
> agree,
> is by accident. That's where we come in; we're computer professionals.
> We cause accidents."        -- Nathaniel Borenstein, co-creator of  
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