Breaking news

It was brought to my attention recently by reputable sources that the recent announcement of increased usage in recent years produced an internal firestorm within Mozilla. Key figures raised alarm that some of the tech press had interpreted the blog post as a sign that Thunderbird was not, in fact, dead. As a result, they asked Thunderbird community members to make corrections to emphasize that Mozilla was trying to kill Thunderbird.

The primary fear, it seems, is that knowledge that the largest open-source email client was still receiving regular updates would impel its userbase to agitate for increased funding and maintenance of the client to help forestall potential threats to the open nature of email as well as to innovate in the space of providing usable and private communication channels. Such funding, however, would be an unaffordable luxury and would only distract Mozilla from its central goal of building developer productivity tooling. Persistent rumors that Mozilla would be willing to fund Thunderbird were it renamed Firefox Email were finally addressed with the comment, "such a renaming would violate our current policy that all projects be named Persona."

Why email is hard, part 8: why email security failed

This post is part 8 of an intermittent series exploring the difficulties of writing an email client. Part 1 describes a brief history of the infrastructure. Part 2 discusses internationalization. Part 3 discusses MIME. Part 4 discusses email addresses. Part 5 discusses the more general problem of email headers. Part 6 discusses how email security works in practice. Part 7 discusses the problem of trust. This part discusses why email security has largely failed.

At the end of the last part in this series, I posed the question, "Which email security protocol is most popular?" The answer to the question is actually neither S/MIME nor PGP, but a third protocol, DKIM. I haven't brought up DKIM until now because DKIM doesn't try to secure email in the same vein as S/MIME or PGP, but I still consider it relevant to discussing email security.

Unquestionably, DKIM is the only security protocol for email that can be considered successful. There are perhaps 4 billion active email addresses [1]. Of these, about 1-2 billion use DKIM. In contrast, S/MIME can count a few million users, and PGP at best a few hundred thousand. No other security protocols have really caught on past these three. Why did DKIM succeed where the others fail?

DKIM's success stems from its relatively narrow focus. It is nothing more than a cryptographic signature of the message body and a smattering of headers, and is itself stuck in the DKIM-Signature header. It is meant to be applied to messages only on outgoing servers and read and processed at the recipient mail server—it completely bypasses clients. That it bypasses clients allows it to solve the problem of key discovery and key management very easily (public keys are stored in DNS, which is already a key part of mail delivery), and its role in spam filtering is strong motivation to get it implemented quickly (it is 7 years old as of this writing). It's also simple: this one paragraph description is basically all you need to know [2].

The failure of S/MIME and PGP to see large deployment is certainly a large topic of discussion on myriads of cryptography enthusiast mailing lists, which often like to partake in propositions of new end-to-end encryption of email paradigms, such as the recent DIME proposal. Quite frankly, all of these solutions suffer broadly from at least the same 5 fundamental weaknesses, and I see it unlikely that a protocol will come about that can fix these weaknesses well enough to become successful.

The first weakness, and one I've harped about many times already, is UI. Most email security UI is abysmal and generally at best usable only by enthusiasts. At least some of this is endemic to security: while it mean seem obvious how to convey what an email signature or an encrypted email signifies, how do you convey the distinctions between sign-and-encrypt, encrypt-and-sign, or an S/MIME triple wrap? The Web of Trust model used by PGP (and many other proposals) is even worse, in that inherently requires users to do other actions out-of-band of email to work properly.

Trust is the second weakness. Consider that, for all intents and purposes, the email address is the unique identifier on the Internet. By extension, that implies that a lot of services are ultimately predicated on the notion that the ability to receive and respond to an email is a sufficient means to identify an individual. However, the entire purpose of secure email, or at least of end-to-end encryption, is subtly based on the fact that other people in fact have access to your mailbox, thus destroying the most natural ways to build trust models on the Internet. The quest for anonymity or privacy also renders untenable many other plausible ways to establish trust (e.g., phone verification or government-issued ID cards).

Key discovery is another weakness, although it's arguably the easiest one to solve. If you try to keep discovery independent of trust, the problem of key discovery is merely picking a protocol to publish and another one to find keys. Some of these already exist: PGP key servers, for example, or using DANE to publish S/MIME or PGP keys.

Key management, on the other hand, is a more troubling weakness. S/MIME, for example, basically works without issue if you have a certificate, but managing to get an S/MIME certificate is a daunting task (necessitated, in part, by its trust model—see how these issues all intertwine?). This is also where it's easy to say that webmail is an unsolvable problem, but on further reflection, I'm not sure I agree with that statement anymore. One solution is just storing the private key with the webmail provider (you're trusting them as an email client, after all), but it's also not impossible to imagine using phones or flash drives as keystores. Other key management factors are more difficult to solve: people who lose their private keys or key rollover create thorny issues. There is also the difficulty of managing user expectations: if I forget my password to most sites (even my email provider), I can usually get it reset somehow, but when a private key is lost, the user is totally and completely out of luck.

Of course, there is one glaring and almost completely insurmountable problem. Encrypted email fundamentally precludes certain features that we have come to take for granted. The lesser known is server-side search and filtration. While there exist some mechanisms to do search on encrypted text, those mechanisms rely on the fact that you can manipulate the text to change the message, destroying the integrity feature of secure email. They also tend to be fairly expensive. It's easy to just say "who needs server-side stuff?", but the contingent of people who do email on smartphones would not be happy to have to pay the transfer rates to download all the messages in their folder just to find one little email, nor the energy costs of doing it on the phone. And those who have really large folders—Fastmail has a design point of 1,000,000 in a single folder—would still prefer to not have to transfer all their mail even on desktops.

The more well-known feature that would disappear is spam filtration. Consider that 90% of all email is spam, and if you think your spam folder is too slim for that to be true, it's because your spam folder only contains messages that your email provider wasn't sure were spam. The loss of server-side spam filtering would dramatically increase the cost of spam (a 10% reduction in efficiency would double the amount of server storage, per my calculations), and client-side spam filtering is quite literally too slow [3] and too costly (remember smartphones? Imagine having your email take 10 times as much energy and bandwidth) to be a tenable option. And privacy or anonymity tends to be an invitation to abuse (cf. Tor and Wikipedia). Proposed solutions to the spam problem are so common that there is a checklist containing most of the objections.

When you consider all of those weaknesses, it is easy to be pessimistic about the possibility of wide deployment of powerful email security solutions. The strongest future—all email is encrypted, including metadata—is probably impossible or at least woefully impractical. That said, if you weaken some of the assumptions (say, don't desire all or most traffic to be encrypted), then solutions seem possible if difficult.

This concludes my discussion of email security, at least until things change for the better. I don't have a topic for the next part in this series picked out (this part actually concludes the set I knew I wanted to discuss when I started), although OAuth and DMARC are two topics that have been bugging me enough recently to consider writing about. They also have the unfortunate side effect of being things likely to see changes in the near future, unlike most of the topics I've discussed so far. But rest assured that I will find more difficulties in the email infrastructure to write about before long!

[1] All of these numbers are crude estimates and are accurate to only an order of magnitude. To justify my choices: I assume 1 email address per Internet user (this overestimates the developing world and underestimates the developed world). The largest webmail providers have given numbers that claim to be 1 billion active accounts between them, and all of them use DKIM. S/MIME is guessed by assuming that any smartcard deployment supports S/MIME, and noting that the US Department of Defense and Estonia's digital ID project are both heavy users of such smartcards. PGP is estimated from the size of the strong set and old numbers on the reachable set from the core Web of Trust.
[2] Ever since last April, it's become impossible to mention DKIM without referring to DMARC, as a result of Yahoo's controversial DMARC policy. A proper discussion of DMARC (and why what Yahoo did was controversial) requires explaining the mail transmission architecture and spam, however, so I'll defer that to a later post. It's also possible that changes in this space could happen within the next year.
[3] According to a former GMail spam employee, if it takes you as long as three minutes to calculate reputation, the spammer wins.

A unified history for comm-central

Several years back, Ehsan and Jeff Muizelaar attempted to build a unified history of mozilla-central across the Mercurial era and the CVS era. Their result is now used in the gecko-dev repository. While being distracted on yet another side project, I thought that I might want to do the same for comm-central. It turns out that building a unified history for comm-central makes mozilla-central look easy: mozilla-central merely had one import from CVS. In contrast, comm-central imported twice from CVS (the calendar code came later), four times from mozilla-central (once with converted history), and imported twice from Instantbird's repository (once with converted history). Three of those conversions also involved moving paths. But I've worked through all of those issues to provide a nice snapshot of the repository [1]. And since I've been frustrated by failing to find good documentation on how this sort of process went for mozilla-central, I'll provide details on the process for comm-central.

The first step and probably the hardest is getting the CVS history in DVCS form (I use hg because I'm more comfortable it, but there's effectively no difference between hg, git, or bzr here). There is a git version of mozilla's CVS tree available, but I've noticed after doing research that its last revision is about a month before the revision I need for Calendar's import. The documentation for how that repo was built is no longer on the web, although we eventually found a copy after I wrote this post on git.mozilla.org. I tried doing another conversion using hg convert to get CVS tags, but that rudely blew up in my face. For now, I've filed a bug on getting an official, branchy-and-tag-filled version of this repository, while using the current lack of history as a base. Calendar people will have to suffer missing a month of history.

CVS is famously hard to convert to more modern repositories, and, as I've done my research, Mozilla's CVS looks like it uses those features which make it difficult. In particular, both the calendar CVS import and the comm-central initial CVS import used a CVS tag HG_COMM_INITIAL_IMPORT. That tagging was done, on only a small portion of the tree, twice, about two months apart. Fortunately, mailnews code was never touched on CVS trunk after the import (there appears to be one commit on calendar after the tagging), so it is probably possible to salvage a repository-wide consistent tag.

The start of my script for conversion looks like this:

#!/bin/bash

set -e

WORKDIR=/tmp
HGCVS=$WORKDIR/mozilla-cvs-history
MC=/src/trunk/mozilla-central
CC=/src/trunk/comm-central
OUTPUT=$WORKDIR/full-c-c

# Bug 445146: m-c/editor/ui -> c-c/editor/ui
MC_EDITOR_IMPORT=d8064eff0a17372c50014ee305271af8e577a204

# Bug 669040: m-c/db/mork -> c-c/db/mork
MC_MORK_IMPORT=f2a50910befcf29eaa1a29dc088a8a33e64a609a

# Bug 1027241, bug 611752 m-c/security/manager/ssl/** -> c-c/mailnews/mime/src/*
MC_SMIME_IMPORT=e74c19c18f01a5340e00ecfbc44c774c9a71d11d

# Step 0: Grab the mozilla CVS history.
if [ ! -e $HGCVS ]; then
  hg clone git+https://github.com/jrmuizel/mozilla-cvs-history.git $HGCVS
fi

Since I don't want to include the changesets useless to comm-central history, I trimmed the history by using hg convert to eliminate changesets that don't change the necessary files. Most of the files are simple directory-wide changes, but S/MIME only moved a few files over, so it requires a more complex way to grab the file list. In addition, I also replaced the % in the usernames with @ that they are used to appearing in hg. The relevant code is here:

# Step 1: Trim mozilla CVS history to include only the files we are ultimately
# interested in.
cat >$WORKDIR/convert-filemap.txt <<EOF
# Revision e4f4569d451a
include directory/xpcom
include mail
include mailnews
include other-licenses/branding/thunderbird
include suite
# Revision 7c0bfdcda673
include calendar
include other-licenses/branding/sunbird
# Revision ee719a0502491fc663bda942dcfc52c0825938d3
include editor/ui
# Revision 52efa9789800829c6f0ee6a005f83ed45a250396
include db/mork/
include db/mdb/
EOF

# Add the S/MIME import files
hg -R $MC log -r "children($MC_SMIME_IMPORT)" \
  --template "{file_dels % 'include {file}\n'}" >>$WORKDIR/convert-filemap.txt

if [ ! -e $WORKDIR/convert-authormap.txt ]; then
hg -R $HGCVS log --template "{email(author)}={sub('%', '@', email(author))}\n" \
  | sort -u > $WORKDIR/convert-authormap.txt
fi

cd $WORKDIR
hg convert $HGCVS $OUTPUT --filemap convert-filemap.txt -A convert-authormap.txt

That last command provides us the subset of the CVS history that we need for unified history. Strictly speaking, I should be pulling a specific revision, but I happen to know that there's no need to (we're cloning the only head) in this case. At this point, we now need to pull in the mozilla-central changes before we pull in comm-central. Order is key; hg convert will only apply the graft points when converting the child changeset (which it does but once), and it needs the parents to exist before it can do that. We also need to ensure that the mozilla-central graft point is included before continuing, so we do that, and then pull mozilla-central:

CC_CVS_BASE=$(hg log -R $HGCVS -r 'tip' --template '{node}')
CC_CVS_BASE=$(grep $CC_CVS_BASE $OUTPUT/.hg/shamap | cut -d' ' -f2)
MC_CVS_BASE=$(hg log -R $HGCVS -r 'gitnode(215f52d06f4260fdcca797eebd78266524ea3d2c)' --template '{node}')
MC_CVS_BASE=$(grep $MC_CVS_BASE $OUTPUT/.hg/shamap | cut -d' ' -f2)

# Okay, now we need to build the map of revisions.
cat >$WORKDIR/convert-revmap.txt <<EOF
e4f4569d451a5e0d12a6aa33ebd916f979dd8faa $CC_CVS_BASE # Thunderbird / Suite
7c0bfdcda6731e77303f3c47b01736aaa93d5534 d4b728dc9da418f8d5601ed6735e9a00ac963c4e, $CC_CVS_BASE # Calendar
9b2a99adc05e53cd4010de512f50118594756650 $MC_CVS_BASE # Mozilla graft point
ee719a0502491fc663bda942dcfc52c0825938d3 78b3d6c649f71eff41fe3f486c6cc4f4b899fd35, $MC_EDITOR_IMPORT # Editor
8cdfed92867f885fda98664395236b7829947a1d 4b5da7e5d0680c6617ec743109e6efc88ca413da, e4e612fcae9d0e5181a5543ed17f705a83a3de71 # Chat
EOF

# Next, import mozilla-central revisions
for rev in $MC_MORK_IMPORT $MC_EDITOR_IMPORT $MC_SMIME_IMPORT; do
  hg convert $MC $OUTPUT -r $rev --splicemap $WORKDIR/convert-revmap.txt \
    --filemap $WORKDIR/convert-filemap.txt
done

Some notes about all of the revision ids in the script. The splicemap requires the full 40-character SHA ids; anything less and the thing complains. I also need to specify the parents of the revisions that deleted the code for the mozilla-central import, so if you go hunting for those revisions and are surprised that they don't remove the code in question, that's why.

I mentioned complications about the merges earlier. The Mork and S/MIME import codes here moved files, so that what was db/mdb in mozilla-central became db/mork. There's no support for causing the generated splice to record these as a move, so I have to manually construct those renamings:

# We need to execute a few hg move commands due to renamings.
pushd $OUTPUT
hg update -r $(grep $MC_MORK_IMPORT .hg/shamap | cut -d' ' -f2)
(hg -R $MC log -r "children($MC_MORK_IMPORT)" \
  --template "{file_dels % 'hg mv {file} {sub(\"db/mdb\", \"db/mork\", file)}\n'}") | bash
hg commit -m 'Pseudo-changeset to move Mork files' -d '2011-08-06 17:25:21 +0200'
MC_MORK_IMPORT=$(hg log -r tip --template '{node}')

hg update -r $(grep $MC_SMIME_IMPORT .hg/shamap | cut -d' ' -f2)
(hg -R $MC log -r "children($MC_SMIME_IMPORT)" \
  --template "{file_dels % 'hg mv {file} {sub(\"security/manager/ssl\", \"mailnews/mime\", file)}\n'}") | bash
hg commit -m 'Pseudo-changeset to move S/MIME files' -d '2014-06-15 20:51:51 -0700'
MC_SMIME_IMPORT=$(hg log -r tip --template '{node}')
popd

# Echo the new move commands to the changeset conversion map.
cat >>$WORKDIR/convert-revmap.txt <<EOF
52efa9789800829c6f0ee6a005f83ed45a250396 abfd23d7c5042bc87502506c9f34c965fb9a09d1, $MC_MORK_IMPORT # Mork
50f5b5fc3f53c680dba4f237856e530e2097adfd 97253b3cca68f1c287eb5729647ba6f9a5dab08a, $MC_SMIME_IMPORT # S/MIME
EOF

Now that we have all of the graft points defined, and all of the external code ready, we can pull comm-central and do the conversion. That's not quite it, though—when we graft the S/MIME history to the original mozilla-central history, we have a small segment of abandoned converted history. A call to hg strip removes that.

# Now, import comm-central revisions that we need
hg convert $CC $OUTPUT --splicemap $WORKDIR/convert-revmap.txt
hg strip 2f69e0a3a05a

[1] I left out one of the graft points because I just didn't want to deal with it. I'll leave it as an exercise to the reader to figure out which one it was. Hint: it's the only one I didn't know about before I searched for the archive points [2].
[2] Since I wasn't sure I knew all of the graft points, I decided to try to comb through all of the changesets to figure out who imported code. It turns out that hg log -r 'adds("**")' narrows it down nicely (1667 changesets to look at instead of 17547), and using the {file_adds} template helps winnow it down more easily.