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.
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