[gaia] Fwd: AI and the SDGs; E2EE Email

Jane Coffin <janercoffin@gmail.com> Sun, 07 January 2024 02:13 UTC

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Date: Sat, 06 Jan 2024 21:13:24 -0500
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Subject: [gaia] Fwd: AI and the SDGs; E2EE Email
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Dear GAIA Friends -

See this newsletter.
Give Mallory Knodel (who is on this list a shout directly) if you would
like to be on her distro.

Be well


Jane R Coffin
Signal, WhatsApp, Text:  +1.202.247.8429



---------- Forwarded message ---------
From: Internet Exchange <noreply@internet.exchangepoint.tech>
Date: Thu, Jan 4, 2024 at 10:21 AM
Subject: AI and the SDGs; E2EE Email
To: <janercoffin@gmail.com>


Sustainable development and AI: Last month I attended the AI & Data
International Symposium in Berlin, which was a two-day event to place the
most pressing issues of our modern world– climate change, economic
inequality, health and governance– as the north star for data-driven
technology solutions. Civil society experts, AI companies and foreign
service officials from across the globe met, discussed, learned and
networked. While data modeling, automation, or even blockchain, have not
suddenly a

Internet Exchange
<https://internet.exchangepoint.tech/r/94b2a84c?m=ec610f24-acd7-496a-a530-f9437202b2b0>
AI and the SDGs; E2EE Email
<https://internet.exchangepoint.tech/r/7f3c1092?m=ec610f24-acd7-496a-a530-f9437202b2b0>
By Mallory Knodel • 4 Jan 2024 View in browser
<https://internet.exchangepoint.tech/r/b731e95e?m=ec610f24-acd7-496a-a530-f9437202b2b0>
View in browser
<https://internet.exchangepoint.tech/r/9b314cd1?m=ec610f24-acd7-496a-a530-f9437202b2b0>
Photo by Markus Spiske
<https://internet.exchangepoint.tech/r/d1c711ab?m=ec610f24-acd7-496a-a530-f9437202b2b0>
/ Unsplash
<https://internet.exchangepoint.tech/r/227a893d?m=ec610f24-acd7-496a-a530-f9437202b2b0>

*Sustainable development and AI:* Last month I attended the AI & Data
International Symposium in Berlin, which was a two-day event to place the
most pressing issues of our modern world– climate change, economic
inequality, health and governance– as the north star for data-driven
technology solutions.

Civil society experts, AI companies and foreign service officials from
across the globe met, discussed, learned and networked. While data
modeling, automation, or even blockchain, have not suddenly arrived, there
is hope against hope that AI can help countries achieve sustainable
development. When it comes to sustainable development and human rights, the
UN's role looms large and many are looking to the development of principles
as guardrails within which companies can develop technical solutions to
extremely difficult problems.

The fact that these extremely difficult problems are somewhat exacerbated
by technology notwithstanding, I found hope in the promise of
hashtag-AIforgood not because AI makes development cheaper (it doesn't),
but by imagining that technology will be used to solve the easy problems so
that strong institutions and people power can be refocussed on solving the
hard ones.

That same week, the UN Secretary General's AI Advisory Body published its
first major output. It's on AI governance and mercifully mentions "human
rights" a lot and "ethics" not at all.
https://www.un.org/sites/un2.un.org/files/ai_advisory_body_interim_report.pdf
<https://internet.exchangepoint.tech/r/f02ca9ff?m=ec610f24-acd7-496a-a530-f9437202b2b0>
------------------------------

*ICYMI:*

   - News in the consumer-stalking-device market includes some more
   privacy-respecting ways to track the trackers
   https://www.wired.com/story/apple-airtag-privacy-stalking-cryptographic-solution/
   <https://internet.exchangepoint.tech/r/695088ab?m=ec610f24-acd7-496a-a530-f9437202b2b0>
   - Software developer and founder Paul Biggar wrote an emotional piece
   about tech's role in Gaza's destruction
   https://blog.paulbiggar.com/i-cant-sleep/
   <https://internet.exchangepoint.tech/r/8a247881?m=ec610f24-acd7-496a-a530-f9437202b2b0>
   - Excellent WaPo editorial on how the battle for democracy will be
   fought and won (Spoiler: Internet censorship circumvention)
   https://www.washingtonpost.com/opinions/2023/12/21/autocracy-democracy-internet-circumvention/
   <https://internet.exchangepoint.tech/r/34fd7765?m=ec610f24-acd7-496a-a530-f9437202b2b0>
   - Delta Chat sits somewhere between encrypted email and messaging (I
   actually use the mobile app for both) and its features have recently
   changed quite a bit https://delta.chat/en/2023-12-13-chatmail
   <https://internet.exchangepoint.tech/r/5c6372f4?m=ec610f24-acd7-496a-a530-f9437202b2b0>

------------------------------

*It's 2024 and encrypted email (still) so bad (but it can be better):*
End-to-end encryption (e2ee) has come a long way in the last decade and is
now in the hands of billions. But that is largely due to encrypted
messaging, not encrypted email. In general, messaging has improved upon
email with respect to usability, speed, discovery and security to the point
that email is used much less. *Setting*
<https://internet.exchangepoint.tech/r/8cb39066?m=ec610f24-acd7-496a-a530-f9437202b2b0>
*aside*
<https://internet.exchangepoint.tech/r/18a9081a?m=ec610f24-acd7-496a-a530-f9437202b2b0>
*that*
<https://internet.exchangepoint.tech/r/0e6584e1?m=ec610f24-acd7-496a-a530-f9437202b2b0>
*anecdotal*
<https://internet.exchangepoint.tech/r/9edecc53?m=ec610f24-acd7-496a-a530-f9437202b2b0>
*observation*
<https://internet.exchangepoint.tech/r/75d52a8c?m=ec610f24-acd7-496a-a530-f9437202b2b0>,
let’s look at the state of end-to-end encrypted email in 2024 and why, I
think, it is still too hard to use and how to fix that.

*Like most internet connections today, emails that are sent and received by
any provider are done so over encrypted transport. But end-to-end encrypted
email is required if email users would not like their emails stored on or
accessible to the email server (the provider), or someone who could gain
access to that server using an attack or a legal order. OpenPGP is the
emergent standard for e2ee email and it uses asymmetric encryption, which
requires users to each generate a key pair and then exchange their public
keys before they can encrypt their communications. This is hard but still
much easier than the alternative scheme, S/MIME, that requires overhead
administrative installation of a certificate. With OpenPGP, it is largely
left up to email applications and email provider webmail interfaces to
implement it, along with the necessary management mechanisms for public key
cryptography. There also exist server-side implementations of OpenPGP that
provide mailing list encryption or support public key sharing. *

In review, the critical and ideally independent but interoperable elements
of e2ee email are:

   - Email delivery service
   - Client or webmail that supports OpenPGP to
      - Create or import a key pair
      - Keep safe the private key
      - Encrypt and decrypt messages
      - Manage, share, trust others’ public keys
   - Public key sharing infrastructure.

With e2ee messaging here to stay, all information exchange platforms should
integrate many aspects of a functional, usable, and accessible e2ee because
the privacy of users depends on the developments in platforms, where
digital literacy is being addressed. The ubiquitous and established use of
e2ee messaging is teaching us all a little something about usable e2ee.

But e2ee email has lagged behind in adoption; very few people use e2ee
email. Those people are using it even less today, because e2ee messaging
can be used for most things.

In an attempt to change that, there have emerged three categories of
modernised encrypted email solutions that use OpenPGP: Incremental changes
to improve usable software, central web services for context-specific
secure messaging, and app-controlled services. They all fall short.

*Incremental changes in email clients isn’t enough*

There are clients but even the two popular ones are, frankly, not how users
choose to read email, opting instead for webmail. Mozilla put Thunderbird
in the hands of an open source community that is driven by donations
because it was unsustainable. And Outlook is a market-consolidated,
enterprise-first product. These email clients– with encryption treated as
an “advanced” feature– are also primarily built for desktops and the future
is mobile.

The mobile-friendly clients seem to be trying a hybrid situation in which
they are walled gardens of app users, even though you can sometimes with
great effort BYOK (bring-your-own-key), meaning you can email other
same-app users with encryption seamlessly, but this doesn’t easily
interoperate with other encrypted messaging such that users can communicate
with one another no matter who their service provider is, eg the major
defining feature of email.

It seems that the calculus for client developers has been: email users
don’t care about encryption, but if they do it must be because they have
attained a high level of technical experience or their employer requires
it. Therefore solutions are technically challenging to implement for
end-users or tailored for enterprise environments.

*Some industries need encrypted email to communicate with everyday folks*

S/MIME is great if you have lots of everyday folks who are using the same
enterprise email solution to do their jobs. It’s good for institutional
security where email can be such a massive vulnerability, from attachments
containing malware to phishing. However, a central authority is in charge
of certificate management, send/receive settings, revoking access,
controlling ingress and egress with filters, and even controlling the
forwarding, printing or copying/pasting of emails. This does not work for
everyday folks who need encrypted email for everyday things.

(Sidenote that there’s like a whole other weird version of corporate
encrypted email that involves an asymmetry when internal and external
people need to email one another, like the messages that come from your
bank or your doctor. The required user behaviours here, eg “click to read
this secure message”,  are not what security experts would recommend. This
is not e2ee, obviously, but it is important to mention these modalities
because their universality indicates that there are various industries,
contexts and needs for actual e2ee email to be ubiquitous.)

*Centralized e2ee email services aren’t healthy*

Eight years after Signal made e2ee messaging apps ubiquitous, we’ve seen
e2ee email like Protonmail, pEp, Tutanota and others replicate this central
control in all three critical ways.

First, many use OpenPGP encryption schemes but not interoperably. They all
make up for this by allowing both the app’s encryption and OpenPGP key
imports but not integrating them.

Second, they hide from the users all key related functions to the point
that exporting one’s private key is done with app-specific “sync” features.

Third, you only get the security benefits if you’re talking to users on the
same platform. This is probably the biggest insult to injury given email is
fundamentally designed to be interoperable.

We need e2ee email that leverages standards, is not centralized, that
interoperates, that presents both a streamlined interface by default and
advanced features for customisation. This is the part where we start to
learn something from e2ee messaging apps while preserving email
interoperability.

*Email is worth saving*

There exists a crucial inevitability of the use of email. It is a more
formal and professional manner of exchanging information. Email sits
somewhere between your DMs and document writing. It is asynchronous. It is
rich. It is what Marshall McLuhan would call “hot.” Making email end-to-end
encrypted for everyone is what we would call *fire emoji*.

The most important reason we need easier e2ee email is that email is
federated and messaging isn’t. Anyone with an email address can send an
email to anyone else with an email address, for better or worse. E2ee
messaging might just catch up to email in terms of interoperability, if the
EU’s Digital Markets Act proves to be effective, which means we find
ourselves in the luckiest timeline: *messaging*
<https://internet.exchangepoint.tech/r/49dd8017?m=ec610f24-acd7-496a-a530-f9437202b2b0>
and *email*
<https://internet.exchangepoint.tech/r/0de2271f?m=ec610f24-acd7-496a-a530-f9437202b2b0>
are growing together to become the best, most encrypted, versions of
themselves.

*Better: Easy end-to-end encrypted email for everyone*

As a reminder, when you download an e2ee messaging app the elements I
mentioned above are not revealed to the user, by default, making them
highly usable. This is achieved by controlling all key-related functions
within the app as a service. E2ee messaging users have keys, the e2ee
messaging app exchanges users’ keys for them, and keys are automatically
tied to the e2ee messaging users’ accounts. The scheme requires the user to
only interface with one thing: An app that asks them to login to use the
service.

   - E2ee messaging
      - User application
         - Keeps keys safe
         - Manages contacts and contacts’ keys
         - Encrypts and decrypts messages
      - User account
         - Creates key
         - Authenticates user
      - Message delivery service

We can re-express this architecture into a list of principles derived from
from the usability of e2ee messaging apps, that don’t yet exist in e2ee
email clients:

   - Make keys invisible BUT also make them accessible. Generate them,
   export them, share them, and consider key transparency.
   - Make contact key discovery easy BUT also keep things usable with or
   without contact import or keys. TOFU (Trust on First Use) is the way!
   - Make it email BUT make it sexy. Email should be feature rich and
   mobile first.
   - Make it interoperable BUT make it encrypted. Email should keep doing
   the most, but with OpenPGP.

Especially with the specter of hard problems in interoperabile encryption
hovering over our precious walled garden e2ee messaging apps, encryption is
email’s crucial opportunity to come back and be relevant again.
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