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To: "Neal H. Walfield" <neal@walfield.org>, Derek Atkins <derek@ihtfp.com>
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From: Ben McGinnes <ben@adversary.org>
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Subject: Re: [openpgp] Reducing the meta-data leak
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On 4/11/2015 1:37 am, Neal H. Walfield wrote:
>=20
> Bryan Ford proposed getting rid of all unencrypted meta-data.  In
> particular, he wanted to get rid of the recipients / number of
> recipients.
>=20
> There are some practical difficulties with this approach,
> which I mentioned above.
>=20
> My proposal is a blue sky idea to avoid having to try to decrypt a
> message with every secret key while (hopefully) making it more
> difficult to get at the list of recipients.

While I don't doubt the good intentions, I fail to see how this has
any real value.  Specifically because of the significantly larger
amounts of meta-data which already leaks from every SMTP exchange
ever.  That's the real threat and that inevitably leads to this
question:

* In what scenario has someone gone to the effort of disguising all
  their SMTP traffic (remailers, tor, whatever), but not selected an
  alias on the OpenPGP key they're using?


Regards,
Ben


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From nobody Mon Jan  4 03:50:16 2016
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Subject: Re: [openpgp] Chunked OpenPGP streams
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On 30.12.2015 at 14:01 Nils Durner wrote:

> Hi,
>
> > I wonder if chunked streams could make their way to RFC4880bis instea=
d.
> > The verification mechanism (MDC or data signature) would be added to
> > each chunk using the intermediate hash value,
>
> I think this goes in the same direction that OAED or online
> authenticating cipher modes are being considered for - see the recordin=
g
> of the last IETF meeting at
> http://recs.conf.meetecho.com/Playout/watch.jsp?recording=3DIETF94_OPEN=
PGP&chapter=3Dchapter_1
>
> Regarding the potential use of online authenticating cipher modes, it
> was discussed during that meeting that there is *some* research on mode=
s
> that *might* be usable with PGP. If anyone can share papers (or
> references), I would appreciate it.


Disclaimer: I am a co-author of the POET submission, and therefore my
suggestions might be biased. :)


As far as I know, the PGP community want to verify the integrity of
individual ciphertext chunks. This goal can be achieved by OAEAD schemes
that support intermediate tags such as
* - ELmDv2  (*http://competitions.cr.yp.to/round2/elmdv20.pdf) or
 - POETv2.01=20
(https://www.uni-weimar.de/fileadmin/user/fak/medien/professuren/Mediensi=
cherheit/Research/Publications/poet_v2.01.pdf).


Best regards,
Christian

=20









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From nobody Mon Jan  4 16:43:47 2016
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From: Daniel Kahn Gillmor <dkg@fifthhorseman.net>
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On Fri 2016-01-01 23:06:13 -0500, Ben McGinnes wrote:
> On 4/11/2015 1:37 am, Neal H. Walfield wrote:
>> 
>> Bryan Ford proposed getting rid of all unencrypted meta-data.  In
>> particular, he wanted to get rid of the recipients / number of
>> recipients.
>> 
>> There are some practical difficulties with this approach,
>> which I mentioned above.
>> 
>> My proposal is a blue sky idea to avoid having to try to decrypt a
>> message with every secret key while (hopefully) making it more
>> difficult to get at the list of recipients.
>
> While I don't doubt the good intentions, I fail to see how this has
> any real value.  Specifically because of the significantly larger
> amounts of meta-data which already leaks from every SMTP exchange
> ever.  That's the real threat and that inevitably leads to this
> question:
>
> * In what scenario has someone gone to the effort of disguising all
>   their SMTP traffic (remailers, tor, whatever), but not selected an
>   alias on the OpenPGP key they're using?

fwiw, there is effort going into protecting some of the SMTP/RFC822
metadata (see the discussions in shutup@ietf.org), which would make this
kind of work within OpenPGP more valuable than it currently is in the
full-metadata-wrapped OpenPGP e-mail use case.

It's worth thinking about this problem from the point of view of a
single message encrypted to a single recipient.  We already have the
mechanisms to deal with multi-recipient messages: A sender who wants to
craft a single message to N people without indicating the number of
people should probably re-build the message N times, with a single
PK-ESK on each.  If they really cares that an observer can't tell that
each recipient is getting the same message, they should presumably
choose a separate SK for each version, and pad each message to different
sizes as well.  We can do all of the above except padding in OpenPGP as
it stands, and padding can often be done in whatever format is being
wrapped by OpenPGP (e.g. a text/plain MIME part consisting of all
whitespace).  Incidentally, the single-pkesk-per-message approach
addresses the smartcard UI/UX concern, and mitigates the
multiple-secret-key UI/UX concern somewhat (the multiple-secret-key
UI/UX concern can be further mitigated by configuration recipient-side).

Implementation work or guidance on avoiding creation of multi-recipient
messages would be good.

With regards to the bloom filter proposal here, i think Tom's concerns
about its viability are worth heeding.  In a single-recipient message,
the bloom filter is effectively just a smaller hash of the key.  The
current PKESK itself already doesn't provide an unambiguous answer to
who a message is encrypted to, since it provides only 64 bits of the
fingerprint, and we know that there are pairs of keys that share their
lower 64 bits of fingerprint.

We could simply reduce the size of that further to get more ambiguity
(the distribution should already be uniform) but the ambiguity is
already on the edge of being a problem for UI (it's not clear whether a
UI should announce "this message claims to be for key XXXXX, which we
have, but cannot be decrypted with it" or "this message claims to be for
keyid XX, and while we have key XXXXX which can't decrypt it, the sender
might have meant some other key").  Yuck.

Removing the metadata of who a message is for seems likely to require
either:

 a) trial decryption on the recipient side (problematic for smartcard
    and multiple-secret-key setups, as Neal and Werner pointed out), or

 b) some sort of racheted shared state between sender and recipient
    (e.g. a briar- or axolotl-style esk, which might provide other nice
    features, like "deletable" ("forward-secret") messages)

While (b) is out of scope for us here until we get 4880bis sorted, if
someone wanted to experiment with that and report back, i'm sure it
would be interesting to several people on the list.

Or maybe there's a (c) option?

       --dkg


From nobody Mon Jan  4 17:24:16 2016
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To: Daniel Kahn Gillmor <dkg@fifthhorseman.net>, "Neal H. Walfield" <neal@walfield.org>, Derek Atkins <derek@ihtfp.com>
References: <87io5j764u.wl-neal@walfield.org> <sjm7flz9muf.fsf@securerf.ihtfp.org> <87h9l36tf1.wl-neal@walfield.org> <56874CB5.7060806@adversary.org> <87d1tgzwi0.fsf@alice.fifthhorseman.net>
From: Ben McGinnes <ben@adversary.org>
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On 5/01/2016 11:43 am, Daniel Kahn Gillmor wrote:
>=20
> fwiw, there is effort going into protecting some of the SMTP/RFC822
> metadata (see the discussions in shutup@ietf.org), which would make
> this kind of work within OpenPGP more valuable than it currently is
> in the full-metadata-wrapped OpenPGP e-mail use case.

With a list name like that I'm just going to have to check it out.

> Removing the metadata of who a message is for seems likely to require
> either:
>=20
>  a) trial decryption on the recipient side (problematic for smartcard
>     and multiple-secret-key setups, as Neal and Werner pointed out), or=

>=20
>  b) some sort of racheted shared state between sender and recipient
>     (e.g. a briar- or axolotl-style esk, which might provide other nice=

>     features, like "deletable" ("forward-secret") messages)
>=20
> While (b) is out of scope for us here until we get 4880bis sorted, if
> someone wanted to experiment with that and report back, i'm sure it
> would be interesting to several people on the list.
>=20
> Or maybe there's a (c) option?

There is, but I can't recall if I've mentioned it on this list or not,
but I know it's been mentioned on gnupg-users because that's how I
found out about it:

http://www.confidantmail.org/

An attempt at side-stepping SMTP entirely and replacing the transport
method with one of the methods used by BitTorrent.  It relies on GPG
for the message encryption and everything is contained within the
encrypted zip.  The only addressing metadata is the key UID which is
of the format of:

any-damn-thing-you-like@somehost-including-tor-hidden-sites-and-i2p-it-do=
esn't-care

It even includes a clever means of achieving forward secrecy, but
arguably it could benefit from hiding the OpenPGP metadata a little
better.


Regards,
Ben


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From nobody Mon Jan  4 19:15:44 2016
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On Mon 2016-01-04 20:23:49 -0500, Ben McGinnes wrote:
>> Removing the metadata of who a message is for seems likely to require
>> either:
>> 
>>  a) trial decryption on the recipient side (problematic for smartcard
>>     and multiple-secret-key setups, as Neal and Werner pointed out), or
>> 
>>  b) some sort of racheted shared state between sender and recipient
>>     (e.g. a briar- or axolotl-style esk, which might provide other nice
>>     features, like "deletable" ("forward-secret") messages)
>> 
>> While (b) is out of scope for us here until we get 4880bis sorted, if
>> someone wanted to experiment with that and report back, i'm sure it
>> would be interesting to several people on the list.
>> 
>> Or maybe there's a (c) option?
>
> There is, but I can't recall if I've mentioned it on this list or not,
> but I know it's been mentioned on gnupg-users because that's how I
> found out about it:
>
> http://www.confidantmail.org/
>
> An attempt at side-stepping SMTP entirely and replacing the transport
> method with one of the methods used by BitTorrent.  It relies on GPG
> for the message encryption and everything is contained within the
> encrypted zip.  The only addressing metadata is the key UID which is
> of the format of:
>
> any-damn-thing-you-like@somehost-including-tor-hidden-sites-and-i2p-it-doesn't-care
>
> It even includes a clever means of achieving forward secrecy, but
> arguably it could benefit from hiding the OpenPGP metadata a little
> better.

This sounds like an effort to hide the SMTP metadata, but doesn't
involve hiding the metadata in the OpenPGP format itself.  While i think
this is a neat idea, i'm not convinced it's addressing the same problems
that (a) and (b) are addressing.

     --dkg


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On 1/4/2016 at 7:43 PM, "Daniel Kahn Gillmor"  wrote:
Removing the metadata of who a message is for seems likely to require
either:

 a) trial decryption on the recipient side (problematic for smartcard
    and multiple-secret-key setups, as Neal and Werner pointed out),
or

 b) some sort of racheted shared state between sender and recipient
    (e.g. a briar- or axolotl-style esk, which might provide other
nice
    features, like "deletable" ("forward-secret") messages)

While (b) is out of scope for us here until we get 4880bis sorted, if
someone wanted to experiment with that and report back, i'm sure it
would be interesting to several people on the list.

Or maybe there's a (c) option?
=====

Maybe a (c) option that combines  aspects of (a) and (b):

[1] Suggesting that users of multiple secret keys have 1 unique e-mail
address for key.
(e.g.  Hushmail allows for unlimited nym e-mail aliases which all go
to the same hushmail account under the primary [non-nym] e-mail
account.)
A user can generate multiple keypairs, assigning a different nym alias
to each of them).

[2] The users should not upload the keys to keyservers, but rather
exchange public keys with whomever they wish to communicate.

[3] They then use the --throw-keyid option, but the receiver knows
exactly which key it is, by seeing to which nym e-mail address it is
sent.

[4] No interceptor knows who the 'true' recipient is, except for
e-mail client, which could be set up to do this without tracking,
(i.e.   
(a) register for the e-mail client under a false name with a pre-paid
no-name credit card
(b) use an e-mail client that allows multiple nym aliases  )
-- just a possible avenue of exploration as to how it might be done
...
vedaal

--=_79a28b169609dbce07cd0ef4b867a6c1
Content-Transfer-Encoding: quoted-printable
Content-Type: text/html; charset="UTF-8"

<span style=3D"font-family: Arial; font-size: 13px;"><br><br>On 1/4/2016 at=
 7:43 PM, "Daniel Kahn Gillmor" &lt;dkg@fifthhorseman.net&gt; wrote:<blockq=
uote style=3D"border-left:solid 1px #ccc;margin-left:10px;padding-left:10px=
;"><br>Removing the metadata of who a message is for seems likely to requir=
e<br>either:<br><br> a) trial decryption on the recipient side (problematic=
 for smartcard<br>    and multiple-secret-key setups, as Neal and Werner po=
inted out), or<br><br> b) some sort of racheted shared state between sender=
 and recipient<br>    (e.g. a briar- or axolotl-style esk, which might prov=
ide other nice<br>    features, like "deletable" ("forward-secret") message=
s)<br><br>While (b) is out of scope for us here until we get 4880bis sorted=
, if<br>someone wanted to experiment with that and report back, i'm sure it=
<br>would be interesting to several people on the list.<br><br>Or maybe the=
re's a (c) option?<br><br>       <br>=3D=3D=3D=3D=3D<br><br>Maybe a (c) opt=
ion that combines&nbsp; aspects of (a) and (b):<br><br>[1] Suggesting that =
users of multiple secret keys have 1 unique e-mail address for key.<br>(e.g=
.&nbsp; Hushmail allows for unlimited nym e-mail aliases which all go to th=
e same hushmail account under the primary [non-nym] e-mail account.)<br>A u=
ser can generate multiple keypairs, assigning a different nym alias to each=
 of them).<br><br>[2] The users should not upload the keys to keyservers, b=
ut rather exchange public keys with whomever they wish to communicate.<br><=
br>[3] They then use the --throw-keyid option, but the receiver knows exact=
ly which key it is, by seeing to which nym e-mail address it is sent.<br><b=
r>[4] No interceptor knows who the 'true' recipient is, except for e-mail c=
lient, which could be set up to do this without tracking,<br>(i.e.&nbsp;&nb=
sp; <br>(a) register for the e-mail client under a false name with a pre-pa=
id no-name credit card<br>(b) use an e-mail client that allows multiple nym=
 aliases&nbsp; )<br><br><br>-- just a possible avenue of exploration as to =
how it might be done ...<br><br><br>vedaal<br>&nbsp;<br><br></blockquote></=
span>
--=_79a28b169609dbce07cd0ef4b867a6c1--


From nobody Tue Jan  5 11:54:56 2016
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On Tue 2016-01-05 14:50:24 -0500, vedaal@nym.hush.com wrote:
> Maybe a (c) option that combines  aspects of (a) and (b):
>
> [1] Suggesting that users of multiple secret keys have 1 unique e-mail
> address for key.
> (e.g.  Hushmail allows for unlimited nym e-mail aliases which all go
> to the same hushmail account under the primary [non-nym] e-mail
> account.)
> A user can generate multiple keypairs, assigning a different nym alias
> to each of them).
>
> [2] The users should not upload the keys to keyservers, but rather
> exchange public keys with whomever they wish to communicate.

this seems like it might be handwaving away a very difficult question...

> [3] They then use the --throw-keyid option, but the receiver knows
> exactly which key it is, by seeing to which nym e-mail address it is
> sent.

if the receiver can see it, then the metadata is present, right?  so
this proposal just moves the metadata out of the OpenPGP block and into
the surrounding RFC822 message.  I don't think that solves the problem.
or am i misunderstanding your proposal?

   --dkg


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From: "Neal H. Walfield" <neal@walfield.org>
To: openpgp@ietf.org
to: Matthew Green <matthewdgreen@gmail.com>
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Subject: [openpgp] mailing list: managing the subscriber list
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Hi,

Back in July, I made a small, informal proposal about adding support
for encrypted mailing lists to OpenPGP:

  http://mailarchive.ietf.org/arch/msg/openpgp/GAIKx4Ud8CcB-D9uPodeGdQgoGc

I now have a bit of free time and have begun fleshing out the design
and adding support for it to GnuPG.

The thrust of the proposal was to add the list of subscribers to an
OpenPGP key and use the existing key distribution mechanisms to ensure
the list is propagated to posters.

There are two main issues: how to store the subscriber list and how to
deal with updates (i.e., subscribe and unsubscribe events).


In my proposal, I suggested storing the subscriber list in a
mailing-list specific key block.  This immediately addresses the
distribution problem: the key servers and the OpenPGP implementations
already solve the key distribution problem.  I see three possible ways
to store the subscriber list.  We store the data in a dedicated
signature subpacket (my original suggestion), in a signature notation,
or use a new packet type.

Subpackets and notations have the disadvantage that the values are
limited to 64k (Sections 5.2.3 & 5.2.3.16).  As such they impose an
artificial limitation, which is particularly relevant if we were to
use them to store the entire subscriber list.  The obvious fix would
be to increase the allowable length of these data structures in
4880bis.


I see two main approaches to dealing with updates.  After each update
either publish the full, updated list (full update mode); or, just
publish the individual events (incremental update mode).

Full update mode is relatively straightforward, but has a significant
disadvantage: since keyservers don't throw away old data, the key
blocks can get big fast.  Concretely, if N people subscribe to a new
mailing list, this will result in N updates, which consume O(N^2)
space.  In incremental mode, N updates only consume O(N) space (but
the hidden constant is likely much bigger).

Incremental update mode's most important weakness is that it can't
easily support hidden subscriber lists.  To hide the subscriber list,
we need to encrypt it so that just authorized posters can read it.
Because a new poster can't read the encrypted list of subscribers, we
have to reencrypt it.  Since the list of subscribers and the list of
posters is normally identical, each new subscription requires
publishing the full list of subscribers.  In other words, incremental
update mode is usually approximately equivalent to full update mode
when encrypting the subscriber list.

Another issue with incremental update mode is that it is possible for
an attacker intercepting the user's key server requests to prevent
some packets from reaching the user.  This attack can be detected by
turning the updates into a hash chain.  Now, a new poster can detect
if there are any missing blocks prior to the most recently received
update.  That is, if there have been four updates, A, B, C and D, and
a requested key block only includes A and C, the user can detect that
at least one update is missing between A and C, but has no way to
determine that D is missing.  In full update mode, C effectively
includes B so a missing B is irrelevant.  In terms of detecting a
missing D, full update mode doesn't help.

Another attack that both approaches are susceptible to, at least for
public mailing lists, is a denial of service attack that results in
enormous key blocks.  To execute this attack, an attacker just needs
to cause many updates.  In practice, this isn't likely to work very
well since the list maintainer has to sign each update and thus such
attacks are likely to be obvious and easily blocked.  Nevertheless,
the mitigation is obvious and still useful in practice: delay and
batch updates.  The delay occurs naturally, because (normally) the
list maintainer has to sign each update.  Batching updates should also
be straightforward since neither approach naturally precludes them.


I think a reasonable approach would be to use a subkey packet for each
subscriber.  The "subkeys" would be bound to the mailing list key in
the usual fashion and unsubscribe events could be handled using
revocations.  Since we only need to save one encryption key per user
and each user's preferences, this fits quite well within the existing
data structures.  A bit of care needs to be taken to ensure that users
can unsubscribe and later resubscribe.  Unfortunately, this approach
doesn't work well with hidden subscriber lists, as far as I can see.

To deal with hidden subscriber lists, I think we have to use full
update mode.  In this case, I think a new packet type is required,
which would be an optionally encrypted message consisting of an array
of encryption keys and user preferences.

To get the best of both worlds, we could support both approaches and
allow the mailing list's requirements to guide the selection, but I'm
not sure that this added complexity is justified.

Alternatively, if we aren't interested in support encrypted mailing
lists to foil mass surveillance and we agree that something like a few
dozen people is the maximum number of people who can keep a secret, we
can just use the existing notation mechanism.


If anyone has any additional thoughts, I'd be happy to hear them.


Thanks!

:) Neal


From nobody Mon Jan 11 03:01:52 2016
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Hello Neal,

You are getting into a topic that has my interest.  To me, a mailing
list is just an example of encryption things to a group.

I read your proposal of back-then, but it is not wholly clear to me:
 * You want to protect the list of subscribers you say; are these the
email addresses or key identities that you wish to protect?
 * You say that you don't like re-encryption; is this for reasons of
efficiency, or for reasons of passing the plaintext through the control
of the list owner (who is likely to subscribe and therefore receive the
text anyway)?

Since mailing lists are sort-of a hack in the mail system, you might
consider doing it entirely differently.  For instance, downloading list
mail over IMAP, which gives subscribers the initiative so they don't
need to present an email address.  Sending might be done over SMTP or
even over IMAP.  Being searchable, this also makes for a great document
repository :)

As for re-encryption efficiency, you could decide to re-package the
session key to (only authorized) public keys; one way you could find
those is from STARTTLS with an OpenPGP credential, but that would impose
restrictions on the mail client, or require it go through a SOCKS proxy
or such.  Towards the latter, we are working on a TLS Pool that could
make it straightforward to build such a proxy, http://tlspool.arpa2.net
and which implements OpenPGP over TLS.

-Rick


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From nobody Mon Jan 11 15:24:15 2016
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Hello Neal,

> Thus, even though I realize it is not
> possible to completely protect the email addresses, I don't want to
> make it too easy to get them.
OK, so your target is to protect from passive observers.  That is clear
enough.
> Likewise, I want to make it possible to protect the key ids as much as
> possible, which can be done using hidden recipients (i.e., using 0x0
> for the key id in the PK-ESK packet).
I think that makes a lot of sense, the key ID being very similar to the
email address.

On a side-note though :- it is trivial to use your existing key and
construct another ID for it; you can use the same key material and make
a self-signature with another timestamp.  The result is a different
fingerprint and so another key ID.  That might be helpful with your
obfuscation plans (blinding all but the last two bytes of the key ID).

Note that it should also possible to take the subkey and hang it under
another public signing key.

You said you lack experience in RFC authoring; if you want to take that
route you probably don't want to overload a given key ID field with
other meaning but instead want to define a new one which simply has two
bytes only or which has a variable size, perhaps prefixed with up to 8
bits "0" and 1 bit "1" to mark the start of a variable-sized ending of
the key ID.

> There are two types of re-encryption that I think are inappropriate:
>
>   - when the mailing list software decrypts and reencrypts each
>     message before forwarding it on to the list of subscriber, and,

You specified below that this is because you consider the system running
your mailing list to be part of the passive observation infrastructure.
>   - using cryptographic reencryption (ala SELS [2], i.e., the mailing list
>     owner has a secret key, each subscriber has a secret key that is
>     an offset of that secret key, and the mailing list software
>     adjusts encrypted messages by each recipient's offset to
>     re-encrypt it).

This approach can work really nicely if the crypto is designed well.  It
is possible to combine (EC)DH keys in very clever ways to achieve such
effects.  Unfortunately, OpenPGP is not interactive enough (it is a
message format spec, after all) to make use of DH for encryption.

> The problem with the mailing list software having access to the
> cleartext is that the mailing list server becomes part of the trusted
> computing base (TCB), which is often undesirable, because we'd like to
> have some untrusted party provide and manage our infrastructure.
> Note: this has nothing to do with the list owner, who, I assume, is
> part of the TCB.

OK, you are mistrusting the hosting provider.  This will be virtually
impossible to do really well, but if it is possible then crypto is the
answer.  A non-technical answer to that is "pay them enough so they will
want to behave".  Another might be to spread the power over a number of
partial providers.  And this quickly brings you to a distributed scheme,
such as a p2p network.

Emails are identified by a Message-ID, for which mid: URIs have been
specified; similarly, attachments can have a cid: URI defined on them. 
No OS resolves those URIs yet, AFAIK, but the long codes they hold might
do nicely as a p2p lookup key (perhaps after hashing).  This defends
from directed attacks, but still not from casual glancing over your
email, which still requires the cryptographic path.
> The problem with reencryption algorithms is that a subscriber can't
> reuse her own secret key.  Instead, she gets a new secret key (sent
> via email, which she has to import) for each mailing list
> subscription.

If you know your crypto algorithms well enough, you might be able to
cook up something different... RSA, DH, ECDH are all more potent than
their everyday applications make you believe.
> (I'm not clear on what you mean by repackaging the session key.  Do
> you have some pointers?)

It's security-wise equivalent to decrypting and encrypting the email,
but more efficient; you use the receiving-end public key to retrieve the
session key from packet type 1, and then produce another packet type 1
holding the session key encrypted to subscribers' public keys. 
Plaintext doesn't pass through the list host, but the power to decrypt
(namely the session key) does.
> These are good suggestions and I appreciate the tips!  You're probably
> right that a good solution can more easily be found by disregarding
> backwards compatibility.  But, in this project, I'm trying to
> determine the best mechanism that doesn't require users to change
> their habits or upgrade their software (other than their OpenPGP
> implementation and then, only for posters, not list subscribers).
I think you are targeting an audience that, if it is to wisely use the
list and not leak to "interested extra subscribers" by letting them in
on the list (had you thought of the signup procedure yet? key management
is always the culprit) will be quite able to change habits.


Good luck with it!
 -Rick


From nobody Mon Jan 11 23:22:03 2016
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From: Werner Koch <wk@gnupg.org>
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On Mon, 11 Jan 2016 23:46, neal@walfield.org said:

> There are two types of re-encryption that I think are inappropriate:
>
>   - when the mailing list software decrypts and reencrypts each
>     message before forwarding it on to the list of subscriber, and,

As soon as you are in the need for a mailing list you have severe opsec
problems which I consider not solvable: You not only need to fully trust
all participants but also need to make sure that _all_ their boxes are
properly secured against attacks.

Adding another box to reencrypt the messages does not change the picture
much more than adding another subscriber.

I heard that Schleuder (schleuder.nadir.org or apt-get install schleuder)
is a matured tool for encrypted group communication.


Shalom-Salam,

   Werner

-- 
Die Gedanken sind frei.  Ausnahmen regelt ein Bundesgesetz.


From nobody Wed Jan 13 07:30:26 2016
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At Tue, 12 Jan 2016 00:24:07 +0100,
Rick van Rein wrote:
> > Thus, even though I realize it is not
> > possible to completely protect the email addresses, I don't want to
> > make it too easy to get them.
> OK, so your target is to protect from passive observers.  That is clear
> enough.

I want to protect the subscriber list from passive observers, but the
message contents from active attackers (i.e., the same assurances that
OpenPGP can provide).

> > Likewise, I want to make it possible to protect the key ids as much as
> > possible, which can be done using hidden recipients (i.e., using 0x0
> > for the key id in the PK-ESK packet).
> I think that makes a lot of sense, the key ID being very similar to the
> email address.
> 
> On a side-note though :- it is trivial to use your existing key and
> construct another ID for it; you can use the same key material and make
> a self-signature with another timestamp.  The result is a different
> fingerprint and so another key ID.  That might be helpful with your
> obfuscation plans (blinding all but the last two bytes of the key
> ID).

I'm not sure how this helps.  AIUI, the key id is used in the PK-ESK
packet so that the OpenPGP implementation doesn't need to try to
decrypt all PK-ESK packets with all available secret keys.  This is
not only potentially slow, but also annoying if the user has multiple
passphrase-protected secret keys or secret keys on smartcards.  In
other words, including the key id in the PK-ESK packet improves
usability for the *message recipient*.  If the message recipient wants
to hide the key id, then the message recipient can use your trick
locally; there is no need to add this to a standard or the mailing
list software implementation.

> Note that it should also possible to take the subkey and hang it under
> another public signing key.

That was one of my concrete proposals for saving the subscribers in my
mail from a few days ago:

  http://mailarchive.ietf.org/arch/msg/openpgp/UuWVSrMu8LEdChEBQgEpBtQR3-Y

> You said you lack experience in RFC authoring; if you want to take that
> route you probably don't want to overload a given key ID field with
> other meaning but instead want to define a new one which simply has two
> bytes only or which has a variable size, perhaps prefixed with up to 8
> bits "0" and 1 bit "1" to mark the start of a variable-sized ending of
> the key ID.

Again, a driving concern is backwards compatibility and, if I
understand your suggestion correctly, you are suggesting a
non-backwards compatible change.  Perhaps this extension is useful to
consider for 4880bis.

> > There are two types of re-encryption that I think are inappropriate:
> >
> >   - when the mailing list software decrypts and reencrypts each
> >     message before forwarding it on to the list of subscriber, and,
> 
> You specified below that this is because you consider the system running
> your mailing list to be part of the passive observation infrastructure.

If I did, then I misstated my position.  I consider the system running
the mailing list software to be a potentially active adversary.

> > The problem with the mailing list software having access to the
> > cleartext is that the mailing list server becomes part of the trusted
> > computing base (TCB), which is often undesirable, because we'd like to
> > have some untrusted party provide and manage our infrastructure.
> > Note: this has nothing to do with the list owner, who, I assume, is
> > part of the TCB.
> 
> OK, you are mistrusting the hosting provider.  This will be virtually
> impossible to do really well, but if it is possible then crypto is the
> answer.  A non-technical answer to that is "pay them enough so they will
> want to behave".  Another might be to spread the power over a number of
> partial providers.  And this quickly brings you to a distributed scheme,
> such as a p2p network.

For the purposes of this exercise, I want to trust the mail server as
much as a normal OpenPGP user trusts an SMTP server.  Namely, an
OpenPGP user reveals the list of recipients to the SMTP server and
relies on the server to forward the encrypted message.

I realize that there are other approaches that reveal less meta-data,
but insofar as they exist today, they are not widely adopted.  I don't
want to say that those fights are not worth fighting, but I am looking
for a short-term solution that provides similar security guarantees
that OpenPGP provides for normal encrypted email.

> > The problem with reencryption algorithms is that a subscriber can't
> > reuse her own secret key.  Instead, she gets a new secret key (sent
> > via email, which she has to import) for each mailing list
> > subscription.
> 
> If you know your crypto algorithms well enough, you might be able to
> cook up something different... RSA, DH, ECDH are all more potent than
> their everyday applications make you believe.

Unfortunately, I'm not that good of a cryptographer.  But if you have
some concrete suggestions of things to look at or keywords to search
for, I'd appreciate it.

> > These are good suggestions and I appreciate the tips!  You're probably
> > right that a good solution can more easily be found by disregarding
> > backwards compatibility.  But, in this project, I'm trying to
> > determine the best mechanism that doesn't require users to change
> > their habits or upgrade their software (other than their OpenPGP
> > implementation and then, only for posters, not list subscribers).
> I think you are targeting an audience that, if it is to wisely use the
> list and not leak to "interested extra subscribers" by letting them in
> on the list (had you thought of the signup procedure yet? key management
> is always the culprit) will be quite able to change habits.

I'm trying to target all OpenPGP users.  I'm not just interested in
helping those who the subject of a targeted attack, but also those who
are unsophisticated, but are interested in inhibiting mass
surveillance.


Thanks,

:) Neal


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Subject: Re: [openpgp] mailing list: managing the subscriber list
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Hi Werner,

At Tue, 12 Jan 2016 08:19:50 +0100,
Werner Koch wrote:
> On Mon, 11 Jan 2016 23:46, neal@walfield.org said:
> > There are two types of re-encryption that I think are inappropriate:
> >
> >   - when the mailing list software decrypts and reencrypts each
> >     message before forwarding it on to the list of subscriber, and,
> 
> As soon as you are in the need for a mailing list you have severe opsec
> problems which I consider not solvable: You not only need to fully trust
> all participants but also need to make sure that _all_ their boxes are
> properly secured against attacks.

As we discussed recently offline, I respectfully disagree and I find
this position difficult to resolve with your stated position of trying
to bring GnuPG and encrypt in general to a wider audience.  This is
also why I'm working on this project in my free time and not on the
clock.

Even if people aren't sufficiently careful, ready-to-use encrypted
mailing listings can hinder mass surveillance (similar to the way
OpenPGP can, I think).  Further, for those who do have the opsec
background and need this protection, a solution that is easier to use
than GnuPG groups + manually updating the subscriber list, is probably
safer.

> Adding another box to reencrypt the messages does not change the picture
> much more than adding another subscriber.

I disagree with this as well.  Someone who hosts many mailing lists
(e.g., google or sf) could abuse their position in a much more
substantive way than a single user.


Thanks,

:) Neal



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On 1/13/2016 at 10:30 AM, "Neal H. Walfield"  wrote:...

I want to protect the subscriber list from passive observers, but the
message contents from active attackers (i.e., the same assurances that
OpenPGP can provide).

...

Again, a driving concern is backwards compatibility and, if I
understand your suggestion correctly, you are suggesting a
non-backwards compatible change.  Perhaps this extension is useful to
consider for 4880bis.
...

If I did, then I misstated my position.  I consider the system running
the mailing list software to be a potentially active adversary.
...

For the purposes of this exercise, I want to trust the mail server as
much as a normal OpenPGP user trusts an SMTP server.  Namely, an
OpenPGP user reveals the list of recipients to the SMTP server and
relies on the server to forward the encrypted message.

I realize that there are other approaches that reveal less meta-data,
but insofar as they exist today, they are not widely adopted.  I don't
want to say that those fights are not worth fighting, but I am looking
for a short-term solution that provides similar security guarantees
that OpenPGP provides for normal encrypted email.

> > The problem with reencryption algorithms is that a subscriber
can't
> > reuse her own secret key.  Instead, she gets a new secret key
(sent
> > via email, which she has to import) for each mailing list
> > subscription.

=====

What you want to accomplish, can be done, (at the expense of backward
compatibility), by allowing split-shared keys:

[1] You, (or the owner of any list using this),  has one
signing/certifiying master key with 'n' encryption subkeys, with the
ID name of the mailing list.

[2] For Encryption, the message is simultaneously encrypted to each of
the n encryption subkeys.

[3] For Decryption, only one share of any subkey, is needed.

[4] Each subscriber of the list is sent one share of one subkey,
encrypted to the subscriber's own keypair.

[5] If, for whatever reason, you distrust a particular subscriber of
'leaking' a share, you can revoke that subkey, and send a signed
notice to all subscribers, and generate a new subkey, signed by your
master key.

[6] No meta-data of the recipient, is leaked in any of the encrypted
messages.
[7] For further secrecy, 

(a) each recipient generates a 'throw-away' web-based e-mail.

(b) then generates a keypair with a with a bogus ID, and sends that
public key to the list for a share to be sent encrypted to this
'throw-away' e-mail address.

(c) the recipient then discards the throw-away e-mail address, and
generates a new one

(d) then asks to be subscribed to the new one, stating that he/she
already has a shared portion of the decryption key
 to this it, and that no share needs to be sent, just the messages
encrypted to the n subkeys.

(e) If all the recipients are instructed to wait after they have
received their 'share', and send their subscription requests to their
new e-mail addresses, all at some pre-arranged time, (e.g. a day
later), then their identity of the individual e-mail, is difficult to
trace to the specific subscriber.

[8] The determination of the 'n' of the 'n' subkeys, is a
cryptographic issue to which I don't know the answer.

I imagine that there is some minimum size of a 'share' below which it
is feasible to brute force the share, but since there is no limit to
the subkeys one can generate, it seems do-able to decide on a share of
'safe' size and proceed, (although the encrypted message can get
*really* bulky and long, if there are many many subscribers.)

[9] It can be made 'backward' compatible, for new subscribers, if 'n'
is large enough to simply just send a pre-existing  share as
subscribers are added.
just a possible suggestion ...
vedaal

--=_f59a8a78ca9cb5ee3f53458f5000c456
Content-Transfer-Encoding: quoted-printable
Content-Type: text/html; charset="UTF-8"

<span style=3D"font-family: Arial; font-size: 13px;"><br><br>On 1/13/2016 a=
t 10:30 AM, "Neal H. Walfield" &lt;neal@walfield.org&gt; wrote:<blockquote =
style=3D"border-left:solid 1px #ccc;margin-left:10px;padding-left:10px;">..=
.<br><br>I want to protect the subscriber list from passive observers, but =
the<br>message contents from active attackers (i.e., the same assurances th=
at<br>OpenPGP can provide).<br><br>...<br><br>Again, a driving concern is b=
ackwards compatibility and, if I<br>understand your suggestion correctly, y=
ou are suggesting a<br>non-backwards compatible change.  Perhaps this exten=
sion is useful to<br>consider for 4880bis.<br>...<br><br>If I did, then I m=
isstated my position.  I consider the system running<br>the mailing list so=
ftware to be a potentially active adversary.<br>...<br><br>For the purposes=
 of this exercise, I want to trust the mail server as<br>much as a normal O=
penPGP user trusts an SMTP server.  Namely, an<br>OpenPGP user reveals the =
list of recipients to the SMTP server and<br>relies on the server to forwar=
d the encrypted message.<br><br>I realize that there are other approaches t=
hat reveal less meta-data,<br>but insofar as they exist today, they are not=
 widely adopted.  I don't<br>want to say that those fights are not worth fi=
ghting, but I am looking<br>for a short-term solution that provides similar=
 security guarantees<br>that OpenPGP provides for normal encrypted email.<b=
r><br>&gt; &gt; The problem with reencryption algorithms is that a subscrib=
er can't<br>&gt; &gt; reuse her own secret key.  Instead, she gets a new se=
cret key (sent<br>&gt; &gt; via email, which she has to import) for each ma=
iling list<br>&gt; &gt; subscription.<br><br>=3D=3D=3D=3D=3D<br><br>What yo=
u want to accomplish, can be done, (at the expense of backward compatibilit=
y), by allowing split-shared keys:<br><br>[1] You, (or the owner of any lis=
t using this),&nbsp; has one signing/certifiying master key with 'n' encryp=
tion subkeys, with the ID name of the mailing list.<br><br>[2] For Encrypti=
on, the message is simultaneously encrypted to each of the n encryption sub=
keys.<br><br>[3] For Decryption, only one share of any subkey, is needed.<b=
r><br>[4] Each subscriber of the list is sent one share of one subkey, encr=
ypted to the subscriber's own keypair.<br><br>[5] If, for whatever reason, =
you distrust a particular subscriber of 'leaking' a share, you can revoke t=
hat subkey, and send a signed notice to all subscribers, and generate a new=
 subkey, signed by your master key.<br><br>[6] No meta-data of the recipien=
t, is leaked in any of the encrypted messages.<br><br><br>[7] For further s=
ecrecy, <br><br>(a) each recipient generates a 'throw-away' web-based e-mai=
l.<br><br>(b) then generates a keypair with a with a bogus ID, and sends th=
at public key to the list for a share to be sent encrypted to this 'throw-a=
way' e-mail address.<br><br>(c) the recipient then discards the throw-away =
e-mail address, and generates a new one<br><br>(d) then asks to be subscrib=
ed to the new one, stating that he/she already has a shared portion of the =
decryption key<br>&nbsp;to this it, and that no share needs to be sent, jus=
t the messages encrypted to the n subkeys.<br><br>(e) If all the recipients=
 are instructed to wait after they have received their 'share', and send th=
eir subscription requests to their new e-mail addresses, all at some pre-ar=
ranged time, (e.g. a day later), then their identity of the individual e-ma=
il, is difficult to trace to the specific subscriber.<br><br>[8] The determ=
ination of the 'n' of the 'n' subkeys, is a cryptographic issue to which I =
don't know the answer.<br><br>I imagine that there is some minimum size of =
a 'share' below which it is feasible to brute force the share, but since th=
ere is no limit to the subkeys one can generate, it seems do-able to decide=
 on a share of 'safe' size and proceed, (although the encrypted message can=
 get *really* bulky and long, if there are many many subscribers.)<br><br>[=
9] It can be made 'backward' compatible, for new subscribers, if 'n' is lar=
ge enough to simply just send a pre-existing&nbsp; share as subscribers are=
 added.<br><br><br>just a possible suggestion ...<br><br><br>vedaal<br>&nbs=
p;<br><br><br></blockquote></span>
--=_f59a8a78ca9cb5ee3f53458f5000c456--


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Hello,

I couldn't help but notice a usecase that is gaining interest fast,
  yet seems to have been conspicuously absent from the WG's discussions:
  tying not an email address, but another kind of account (typically,
  so-called “social media”) to the OpenPGP key.

I believe this is relevant for two main reasons:
- enabling authenticated/encrypted communication over those services;
  this is the most immediate use, but perhaps not the most relevant;
- enabling people to establish secure communication channels with other
  users of such service; in that case, the identity they want to link to
  a key is not a (name, email) pair but a (username, service) pair.


A popular implementation of this is keybase.io, which make users publish a
  signed, parseable claim of ownership of the account in some location
  where only the account holder (and the service provider) can publish.

Unfortunately, keybase.io does so by acting as a central database[0] where
  users can publish URLs to the proofs of ownership.


However, I believe it should be possible to support that usecase without
  relying on a third-party database, by extending the notion of uid
  beyond mail addresses.  I would feel natural to use URIs there (or a
  subset thereof), as they work for designating a variety of things
  a user might wish to associate with their identity.

This makes verifying the ownership of an uid harder: in the case of email,
  it is done safely (by tools such as `caff`) by sending the signature as
  an encrypted email.  In our case, the 'acct' scheme is only an abstract
  identifier, and does not specify how to interact with the service.

It would be possible to specify the use of a given protocol, such as
  Web Finger [RFC 7033], to obtain the proof of ownership for the account.
  On the other hand, that solution would require active cooperation from
  the service, whereas the current, adhoc solution does not.

Moreover, certain services have strong size limitations, which would not
  allow publishing complete signed proofs of ownership (assuming we do not
  require the service to implement Web Finger or somesuch).  That can be
  handled by storing only a hash of the proof on the service, and either
  storing the proof as a key packet or storing a URL where the proof can
  be fetched.  In both cases, I do not believe it can be done for the
  current OpenPGP spec.


I hope this mail was readable, I'm afraid it has quite a bit of content.

Please take it as a request to discuss whether broadening the notion of
  uids would be relevant, what would be the “right” thing to use as a uid
  and how to actually check the validity of an uid.


Best regards,

  Keller Fuchs


[0]: I am aware that keybase now publishes their database in the Bitcoin
     blockchain.  keybase still acts as the single publisher for it,
     so this doesn't address the issues raised here.

