Re: [openpgp] Can the OpenPGP vs. S/MIME situation be fixed?

Watson Ladd <watsonbladd@gmail.com> Sun, 03 July 2016 14:47 UTC

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From: Watson Ladd <watsonbladd@gmail.com>
Date: Sun, 3 Jul 2016 07:47:01 -0700
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To: Phillip Hallam-Baker <phill@hallambaker.com>
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Cc: Derek Atkins <derek@ihtfp.com>, IETF OpenPGP <openpgp@ietf.org>, =?UTF-8?Q?Hanno_B=C3=B6ck?= <hanno@hboeck.de>, Peter Gutmann <pgut001@cs.auckland.ac.nz>
Subject: Re: [openpgp] Can the OpenPGP vs. S/MIME situation be fixed?
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On Sat, Jul 2, 2016 at 5:24 PM, Phillip Hallam-Baker
<phill@hallambaker.com> wrote:
>
>
> On Sat, Jul 2, 2016 at 11:08 AM, Peter Gutmann <pgut001@cs.auckland.ac.nz>
> wrote:
>>
>> Phillip Hallam-Baker <phill@hallambaker.com> writes:
>>
>> >I have wanted this for a long time. there are actually three separate
>> >problems to be solved.
>> >
>> >1) How to make S/MIME work with OpenPGP credentials
>> >
>> >2) How to make OpenPGP work with S/MIME credentials
>> >
>> >3) How to merge the two specifications into one.
>>
>> The first two are pretty easy, I've been doing that for years.  For
>> S/MIME,
>> use the subjectKeyIdentifier form of the key ID.  For PGP, use an
>> issuerAndSerialNumber in a type-and-value subpacket.
>>
>> The third is impossible.  While at an abstract level PGP and S/MIME do the
>> same thing, the bit-bagging formats used to encode the abstraction are
>> completely incompatible.  You can't make them compatible without either
>> moving
>> S/MIME to the PGP format or PGP to the S/MIME format.  I can't see either
>> of
>> those happening...

The other issue, which is sadly overlooked, is implementation
simplicity and UX. Both OpenPGP and S/MIME fail hard on this front for
reasons that cannot be fixed easily. If Adam Langley and I cannot
easily send encrypted emails to each other (fun story about a summer
internship I had) without screwing up multiple times, what hope for
the rest of us? Has anyone fuzzed S/MIME clients to see if they parse
X509 correctly? My guess is some do, most don't, and you will find
exploitable bugs.

>
>
> That would clearly be impossible if it was what was being proposed.
>
> What I am suggesting is rather different, A new application for managing
> encrypted content, Word, Powerpoint, PDF, etc. that has crypto designed into
> the metal and also provides a messaging capability.
>
> I am suggesting Blu Ray, not trying to develop adapters to play VHS on
> Betamax.
>
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