We need a modern design for a successor protocol to email, and no one is working on it because they prefer instant messaging (or think other people do).
Everything would have to support SMTP as a fallback for the lot of people that just don't care and thus couldn't actually improve.
One day, a while after they become usable and common, people will just realize they've been sharing documents E2EE in place of sending email, and they'll be using it for basically everything that matters.
It would be a proper restart and allow for significant improvements in usability and security and everything else.
Not OP but I can definitely say that's a yes from me after doing this repeatedly. I cold email people once a month or so, and if it is to do with anything sensitive I'll check to see if a public key is available for them (on their website is best, else I check a public key server and use that key as long as there is only one listed).
I get a better response rate from PGP/GPG users too, I can only recall one not responding to an encrypted message and I sent a follow-up message unencrypted which they responded to.
I think it's important to send PGP messages for ordinary communications whenever possible, because this normalizes it and may increase the workload for those trying to defeat it.
Honestly, I wouldn't focus on (3), because as I see it, if you can replicate the feel of email, things like (1)-(2), so that it can replace email in contexts without (3), then (3) will just come naturally as it slowly replaces email.
Edit: All this is assuming it isn't tied to a phone number or something similar, of course!
The "Web of Trust" [0] fills that role:
> As time goes on, you will accumulate keys from other people that you may want to designate as trusted introducers. Everyone else will each choose their own trusted introducers. And everyone will gradually accumulate and distribute with their key a collection of certifying signatures from other people, with the expectation that anyone receiving it will trust at least one or two of the signatures. This will cause the emergence of a decentralized fault-tolerant web of confidence for all public keys.
[0]How it caused a problem: I added an email address to my public key (or maybe it expired or something, I forget), and asked people to refresh their copy of my key. One person instead downloaded it entirely anew from a keyserver and got the old one. Oops. (Admittedly I didn't explicitly use the word "refresh".) Anyway yeah -- though this problem had happened to me, it hadn't ocurred to me that it might be common; maybe this is more of a problem than I thought...
While this is bad, the keyserver issue is still valid.
I just don't get the encrypted email obsession. It's impossible for an individual to withstand a targetted cyber attack so it seems pointless to go above and beyond to ultra encrypt every little thing
Well, first of all, "breaking in" isn't the only way someone might get access to data on Google's servers. There are such thing's as subpoenas, not to mention that it is possible a Google employee might abuse access to servers. And then I would be _very_ surprised if google doesn't use the content of your emails for advertisement and tracking purposes.
Furthermore, unless both parties are using gmail, the email will be stored at least temporarily on other mail servers, which may be less secure (and you might not even know who controls them).
That would go against their own privacy policy. But they are one change away from doing it.
https://safety.google/privacy/ads-and-data/
> Google does not use keywords or messages in your inbox to show you ads. Nobody reads your email in order to show you ads.
https://www.nytimes.com/2017/06/23/technology/gmail-ads.html
They eventually stopped, although the phrasing of the privacy policy is vague enough that, as wodenokoto mentions above, I wouldn't be surprised if email messages were still scanned for some advertising purposes. The fragment on the page you link to is only about ads shown in Gmail, doesn't exclude using keywords and messages for tracking, classifying etc. (it just doesn't use them "to show you ads") and doesn't actually exclude using programs to process messages (i.e. you can still reasonably say that "nobody reads" messages if you just feed them into a program). It's also not very obvious if "messages in your inbox" also includes messages you send.
FWIW, I think the policy is deliberately open-ended so as to be future-proof, but I doubt emails are an important source of advertising data today, so I think it's likely that Google doesn't rely on it that much anymore. Most sources of legitimate (i.e. non-spam email) that are useful for advertising -- e.g. online shops and the like -- already track you and show you ads, and Google is already deeply embedded there. Millions and millions of personal accounts are an useful strategic asset to have but I think there are better sources of data.
I completely disagree with the first part of your assertion. Email is still the main medium for all organizations, especially private companies taking your money for something, to communicate with you with plenty of details. Be it ordering some product online or booking a flight or other travel ticket or ordering a service or anything else.
The richness and amount of information conveyed over email pales in comparison to SMS notifications. So email is still a treasure trove of what people are doing and have done.
That's true, but all these places already track the living hell out of you. Even the newsletters they send over email have tracking information. By the time they've sent you an email after your first purchase, they know everything they need to show you relevant ads (in fact, that's probably why you made the first purchase...). I doubt bulk analysis of emails can show anything that is not already known way before the emails got sent.
Google can probably serve nice ads just based on metadata it gathers on the SMTP level, without even using the raw message. Someone mails his bank, maybe show some banking related e-mails, etc.
And it would still stay true to the proclamation on that page.
It was never a conspiracy theory. Google used to be very open about the fact that they were scanning emails.
What changed was gsuit. They want to move away from the “we are harvesting your emails” image, in order to better sell paid accounts
“Consumer Gmail content will not be used or scanned for any ads personalization after this change.”
https://blog.google/products/gmail/g-suite-gains-traction-in...
So the only people who can read email are you, your counterparty, your ESP, and your counterparty's ESP, assuming the email providers are following good practice.
One further note is that you can know post-hoc if an email was delivered to Gmail via TLS by the presence or absence of a red lock in the Gmail app or web UI.
Not only that, but intentionally downgrading STARTTLS commands has as times been the default configuration for some Cisco routing gear.
(Buy me a beer one day and I might tell you about the time I charged one of Australia's big four banks about $70k to debug that in a router on their internal network that nobody there knew existed...)
STARTTLS isn't a problem, the problem is if a user checks a box (or moral equivalent) saying it's optional obviously bad guys will opt for "No". If your client is set to _require_ STARTTLS, then an adversary blocking STARTTLS has the same effect as if they just blocked the IP address of the mail server, you get an error and it doesn't work.
There's no reason to use "opportunistic" STARTTLS for your own mail servers (ie IMAP or SMTP to an outbound relay). Nobody should be configuring their own gear, or corporate gear, to just let somebody else decide whether it uses encryption.
Opportunistic encryption still has a place in server-to-server SMTP relaying, but if you're choosing options like "if available" in a desktop/phone mail client that's wrong.
This is a trivial attack vector not just for state-actors, but also stupid kids: in the early 2000s, I announced Microsoft's AS from my own network (AS21863) to see what would happen and got a significant amount of microsoft.com's traffic. There was no security, and there still isn't: Most multihomed sites that change links frequently inevitably find themselves unfiltered either through accident or misplaced trust.
For this reason, TLS without key-pinning (even with IP filtering, as is popular with a lot of banks/enterprise) is far less secure than people realise, and on unattended links (server-to-server relaying) it offers only some casual confidentiality (since detection is unlikely) at best.
If you use MTA-STS, you have a good chance of detecting this kind of attack though. I've not seen anyone use a long policy on a distant but popular network to require someone BGP hijack two big networks to beat it, but I suspect such a disruption would be felt across the Internet.
See SMTP MTA Strict Transport Security (MTA-STS):
* https://tools.ietf.org/html/rfc8461
And STARTTLS Everywhere:
Most e-mail servers required a login (regardless of fetching or sending), and it would take a real incompetent sysadmin to allow that to happen in the clear.
That's actually more complicated than that.
If you're using a web mail, your connection to the mail provider most likely uses HTTPS. That is, HTTP over TLS. When the mail is sent, it depends whether the recipient uses the same provider or not. If it's the same provider, well, protocols are irrelevant. If not, it will usually be SMTP over TLS (minus any potential problems with STARTTLS).
The main problem with that is that the mail is not encrypted on the various servers it goes through. Only the server-to-server connections are encrypted. So your provider can access your email, and so can the recipient's. When that provider's business model is reading your emails so it can send you targeted adds, this is less than great. (Yes, Google reads your emails. They try to reassure you by telling you their employees don't read it, but the fact the process is automated actually makes it worse.)
Each one of those hops may or may not have talked TLS to the next hop. Each one probably wrote the mail out to a disk based mail queue in plaintext. There is nothing preventing any of those 7 servers from keeping around that mail even though they forwarded it on. There is nothing preventing them from indexing the mail for spam or marketing purposes.
It is possible for a determined individual to withstand targeted attacks if he’s careful and willing to make the sacrifices that come with the territory.
the problems with email are that, no matter how sure you are that the connection between you and your mail server, and your local and server storage, are secure, the parties you may be interacting with are not. And then, as is talked about in the article, your recipient forwards the mail as plaintext...
Not supported by everyone just yet since this is a new standard, but Gmail at least supports it.
E.g., things distinguishing how email is used from how text-messaging is used:
1. Email is potentially long-form. I sit down and type it from my computer. Text-messaging is always short, although possibly it's a series of short messages. A series of short emails, by contrast, is an annoyance; it's something you try to avoid sending (even though you inevitably do when it turns out you got something wrong). Similarly, you don't typically hold rapid-fire conversations over email.
2. On that point, email says, you don't need to read this immediately. I expect a text message will be probably be read in a few minutes, and probably replied to later that day (if there's no particular urgency). I expect an email will be probably read in a few hours, and probably replied to in a few days (if there's no particular urgency).
3. It's OK to cold-email people. To text someone you need their phone number; it's for people you know. By contrast, email addresses are things that people frequently make public specifically so that strangers can contact them.
So what am I supposed to do for secure messaging that replicates that? The best answer I've gotten for this so far -- other than PGP which is apparently bad -- is "install Signal on your computer in addition to your phone and just use it as if it's email". That's... not really a satisfactory answer. Like, I expect a multi-page Signal message talking about everything I've been up to for the past month to annoy its recipient, who is likely reading it on their phone, not their computer. And I can't send someone a Signal message about a paper they wrote that I have some comments on, not unless they're going to put their fricking phone number on their website.
So what do I do here? The secure email replacement just doesn't seem to be here yet.