Google Apparently Trying To Make Encrypted Email Easier

from the and-it-should dept

Wed, Apr 23rd 2014 11:57pm — Mike Masnick

About six months before Ed Snowden leaked his documents, we had written a post about why Google should encrypt our email, based on a bit of back-and-forth between Julian Sanchez, arguing why Google should encrypt all email, and Ed Felten, who noted it's not as easy as it sounds (though Julian highlighted how none of the problems Felten raises are insurmountable). There are, of course, already ways that you can add PGP encryption to Gmail, with tools like Mailvelope, but it can be a little kludgy, and not exactly foolproof. Still, many have insisted that Google would never go this route, since it would limit the company's ability to target ads based on the contents of email.

However, VentureBeat is reporting that, partly inspired by all of the Snowden revelations, researchers at Google are looking at ways to make encryption much easier within Gmail. While the report suggests that Gmail won't go site-wide end-to-end encryption, anything it does to bring real encryption more into the mainstream would be a good thing -- though it might make the NSA and DOJ freak out. But, as we've seen, well-done crypto does work. The problem is that so much crypto is not particularly well implemented, leading to all sorts of leaks. Still, it's encouraging to hear that Google is working on something, and hopefully it releases something that is both user-friendly and open to some sort of audit to ensure that it's safe.

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Filed Under: email, encryption, gmail, pgp
Companies: google

42 Comments

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Aalewis, 24 Apr 2014 @ 12:06am

Google will never do this in a way that is safe, they won't be able to earn from ad revenue from scanning email contents.
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Andy B, 24 Apr 2014 @ 12:44am

Secure E-communications is a gold mine
If Google and some of the other giants don't tackle the spying issue head-on, then some of their developers, or others will grab this market.

There is a huge market needing product right now. Why not pay $200 a year for secure, seamless email, truly private browsing, encrypted chat and video? When I say seamless, I mean integrated with calendars, contacts, etc. Imagine "Secure Google" where you are the customer, not the product. Easily worth $200 a year.

Folks will be ashamed and shamed into using this type service by friends who do not want their data mined with every communication. It is coming. Who will make this fortune?
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Anonymous Coward, 24 Apr 2014 @ 12:53am

Google should not be responsible for encrypting anybodies email, other than at a ssl/tls level. The problem is that convenient email encryption, by letting a third part encrypt the email, is not secure, nor is building encryption support into Internet enabled software. (In a capabilities based system, encryption software can be prohibited from connecting to networks so long as it is standalone. Obviously mail programs need to connect to networks. As for the idea of using a browser embedded scripting language to carry out encryption... shudder; security is totally dependent of the downloaded software, so may be OK today, but tomorrow. send keys straight to NSA)

Security of encryption requires users to create manage and collect other peoples keys in a secure and verifiable manner, along with safe practices for handling decrypted messages. Any programs used for encryption and decryption should be separate programs, both for auditing purposes, and to allow for the possibility to encrypt and decrypt messages on an isolated machine. Manual work flow with separate programs for editing, cryptography and communications is the foundation of communication security. While this is inconvenient for most people, making use of cryptography more convenient also makes it less secure.
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Anonymous Coward, 24 Apr 2014 @ 1:26am

The problem with doing crypto in web browsers, is browsers are complex pieces of software with a large attack surface. Browsers have Java, JavaScript, iFrames, Cross-Site Scripting and Adobe Flash/Acrobat. Just to name a few attack avenues.

Gmail should still add OpenPGP support despite all this. At least then government snooping will hopefully be a little more targeted. Forcing law enforcement to file backdoor requests for specific Google users, instead of just scooping up everything as it passes over the wire unencrypted.

Hopefully https://www.mailpile.is will offer us an easy to setup and use, secure FOSS email client. It's currently in alpha stage. It appears the MailPile team will make cross-platform builds available for Windows, Linux, Android, iOS, OS X, and BSD. According to their FAQ page.
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toyotabedzrock (profile), 24 Apr 2014 @ 1:38am

They could just use JS to scan the mail when it is read.

Or they could scan all the mail that everyone gets that is not encrypted. Like from Newegg, Amazon and news letters etc. That would be more valuable to them for advertising purposes I think.
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Anonymous Coward, 24 Apr 2014 @ 2:40am

though it might make the NSA and DOJ freak out
Is there anyone at all in the NSA/DOJ/CIA/FBI/ETC with enough functioning gray matter to understand that a more secure public is the direct consequence of their own actions? That if the increased personal security somehow does in fact lead to a terrorist attack, that it will be entirely their fault for deliberately spying on absolutely everyone?
Are there any adults there; anyone mentally capable of taking responsibility for their actions?
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Anonymous Coward, 24 Apr 2014 @ 2:50am

This is PR posturing by Google -- don't fall for it
Gmail is run by mere ignorant newbies, who don't understand email, user interfaces, privacy, security, phishing, spam or much else. It's not their fault that they're inexperienced, of course, but it does explain why Gmail is so badly designed and operated. Granted, it's slightly better than Yahoo and MSN and AOL, but that's like pointing out that the newer Portajohns stink less than the old ones: they're still all shitholes and are avoided by everyone who actually cares about quality email service.

Google can't solve this problem because the only encryption you can trust is that which you do yourself: doing it inside their client has no value, not just because you can't trust any third party, but because if this actually goes anywhere, they'll be presented with an NSL which demands they place a back door in for the NSA. That backdoor will specifically target users utilizing encryption because of course the early adopters will be considered suspicious, e.g., "What have you got to hide?"

And that's just one intelligence agency from one country. Don't you think that the Brits and the Chinese and the Russians and everyone else has made an effort to subvert these operations? Freemail providers are huge targets and particularly tempting ones because they're so poorly run: there's no way, NO WAY, that they haven't been thoroughly infiltrated by now. (Even spammers have no trouble at all getting into them, and they don't have nearly the resources and intelligence of spy agencies.)

Want privacy? Don't use freemail providers. Get your friends and colleagues and everyone else to stop using them. If your school/business was stupid enough to outsource to one of them, take the email operation back.
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Anonymous Coward, 24 Apr 2014 @ 3:05am

i've even stopped signing my mail because the idiot gmail and hotmail users thought it was spam.

Any decent e-mail client makes PGP-encrypted mail totally transparent and a breeze to use. Encrypted e-mail is not hard, but people just can't be arsed enough to even do the simple things.
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Ninja (profile), 24 Apr 2014 @ 3:13am

Re: Secure E-communications is a gold mine
I wonder. How much does Google make per user with advertising? $10 per month? I would gladly pay a few pennies to make end-to-end encryption the standard and grab my privacy back. Maybe there's money to be made here?
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Ninja (profile), 24 Apr 2014 @ 3:16am

Re:
I wonder if you could implement such separate software as modules in a browser using html5 or some public standard that's widely accepted. You'd only need to keep the local keys well stored, no?
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Ninja (profile), 24 Apr 2014 @ 3:20am

Re: This is PR posturing by Google -- don't fall for it
Gmail is run by mere ignorant newbies, who don't understand email, user interfaces, privacy, security, phishing, spam or much else.

Really? I take it you are a genius?

Gmail is run by very competent people (that can still err at times). They know there's a trade off between privacy and security and they also know they need to make money with their product. Finding a balance here is a delicate thing. If they can move any inch towards security without sacrificing usability then why not? Sure it will not be perfect security but if you do need perfect security then you know you shouldn't be using free mail providers as you just said.

Gratuitously attacking Google doesn't help.
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Anonymous Coward, 24 Apr 2014 @ 3:48am

Re: Re:
If you do that, the security of the encryption system is dependent on the browser security, and as a comment below points out, the decrypted email will be available to JS, along with Interface elements. Further if you download the module every time you use it, there is no protection against it being replaced. You can have convenience, or you can have security.
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Anonymous Coward, 24 Apr 2014 @ 4:26am

Re: Re: This is PR posturing by Google -- don't fall for it
"Really? I take it you are a genius?"

No. Of course not. However, I've been doing this a LOT longer than the noobs at Gmail, who have made and continue to make rookie-grade mistakes that everyone knows are mistakes. I'm not faulting them for getting the difficult edge cases wrong: we ALL get those wrong from time to time. I'm faulting them for getting the fundamentals wrong, the things that you're supposed to learn in the first hour of the first day of Mail System Operation 101.

That's part of the problem. Here's the other part: their mission is not to run an email service. Their mission is to capture eyeballs and data in order to make money for Google. So if, at any point in the design and implementation process, there is a decision that needs to made, and of the options maximizes revenue -- that's the one that is chosen. This isn't the fault of the Gmail team, per se; they're merely following orders. But it does mean that they've done a lot of things that range from questionable to dubious to wrong to stupid, because those things all help Gmail to fulfill its fundamental purpose: eyeballs and data.

Expecting that to change is ridiculously naive. Of course it won't. Google didn't built Gmail out of the goodness of its heart because they wanted to do something nice for the Internet: they built it to make money. And there's nothing wrong with making money, BUT let's not pretend for a moment that it's otherwise, that there is some noble and grand purpose behind Gmail. It's just another steaming pile of crap like Yahoo's mail operation and MSN's mail operation and AOL's mail operation (which has degraded terribly since they fired their entire senior postmaster team). And sprinkling gold dust on it with faux encryption doesn't change that. This isn't a serious technical effort to increase privacy and security: if Gmail wanted to do that, there are a whole BUNCH of things they could have done a long time ago. This is just PR happytalk bullshit.
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Anonymous Coward, 24 Apr 2014 @ 4:36am

I still like the DarkMail protocol much more. Too bad it's not finished yet. Mailpile said they would support both PGP and DarkMail. Maybe Gmail should do the same. DarkMail can also protect metadata and you can host the e-mails on servers other than Google's too, and Google would basically just fetch a link, and prompt you for a password (or use your client-side key by default to open it).
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Mike Masnick (profile), 24 Apr 2014 @ 5:55am

Re: This is PR posturing by Google -- don't fall for it
Gmail is run by mere ignorant newbies, who don't understand email, user interfaces, privacy, security, phishing, spam or much else.

Almost none of that is true, but ok.

Google can't solve this problem because the only encryption you can trust is that which you do yourself: doing it inside their client has no value, not just because you can't trust any third party, but because if this actually goes anywhere, they'll be presented with an NSL which demands they place a back door in for the NSA.

You assume that Google's solution will be inside their client. It need not be. It is possible to build encryption for webmail in which the keys stay locally and everything is done locally before moving the encrypted results back into the web client.
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mcinsand, 24 Apr 2014 @ 6:35am

Re: Re: This is PR posturing by Google -- don't fall for it
AC's original comment in this thread was mainly idiocy, except for the remarks about the user interface. There is definitely a group of arrogant morons at Google in charge of gmail's UI. Organized e-mail is nice, but it has to be organized by the user. Whoever decided to start sorting into folders without involving the user needs to have his/her fingers broken to keep those involved from ever programming again. I have missed several important messages because gmail decided what would be buried in a 'social' folder that I generally ignore.
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Anonymous Coward, 24 Apr 2014 @ 6:42am

Re: Re: This is PR posturing by Google -- don't fall for it
It is possible to build encryption for webmail in which the keys stay locally and everything is done locally before moving the encrypted results back into the web client.

PGG/GPG does that already, along with the safe requirement for users to manage their own keys. Apart from user interface details, this is as convenient as it gets without introducing weaknesses into key management or plaintext management which potentially render the cryptography useless. Assuming that the OS is sensibly secure, you do not want the plaintext or keys being used by a web enabled application, and especially a web browser, as they may be subverted, or give access to the displayed text to third party software.
Note relying on a third party to carry out key management always introduces the risk of the recipient not being who you think they are, or there being a man in the middle reading the traffic. The latter is much more easily achieved if hosted email is being used, as the hosting company is in the middle, and can be coerced into cooperating with governments.
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Anonymous Coward, 24 Apr 2014 @ 6:57am

Re: Re: Re: This is PR posturing by Google -- don't fall for it
It's weird how you haven't even bothered to provide even one example.
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jupiterkansas (profile), 24 Apr 2014 @ 7:53am

Re: Re: Re: This is PR posturing by Google -- don't fall for it
You can turn off the auto sorting you know and do it yourself, but it actually works pretty good, and you can resort messages to go to different folders if you don't like where they end up.
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Ninja (profile), 24 Apr 2014 @ 7:55am

Re: Re: Re:
Not if they are installed locally? The mail software is also a vulnerability, no?
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ltlw0lf (profile), 24 Apr 2014 @ 8:07am

Re: Re: Re:
You can have convenience, or you can have security.

While it is true that convenience and security are mutually exclusive, the truth is also that perfect security is unobtainable, and no matter what you do, someone may come along and undo everything you have done. The goal is to manage risks, not avoid them entirely.

There are protections against modules being replaced. Its called cryptographic hashing, and its existed for at least 30 years. While the browser will have to be modified to include this hashing capability, it wouldn't be terribly difficult.

Browser security will need to be hardened some, but it would be far easier to trust that nobody is listening on your computer versus nobody listening on Google's servers.
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Pessimist, 24 Apr 2014 @ 8:13am

Google encryption
Google's use of encryption, both https and in email, is based on profits. The more encryption that is used in the Internet, the more entities like the NSA, FBI, KGB, et. al. will need to PAY GOOGLE for decrypted copies. As the middleman controlling the encryption, Google will be in the monopoly position and able to charge anything they want.

In the U.S. Google must obey court orders (including secret courts), but the courts have firmly supported the idea that the government must pay for the effort!

Ergo, Google encryption is about profits.
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Anonymous Coward, 24 Apr 2014 @ 8:33am

Re: Re: Re: Re:
Integrating anything with the browser is a security risk, and anything visible on screen is available to other loaded components. Mail software is a possible vulnerability, which is why I would recommend a manual work-flow. It offers the maximum separation between plan text and keys and any network enabled software; which minimizes the exposure to exploits.
As soon as you start integrating software, even in a modular fashion, other than by bash or similar scripting languages/shells, security is dependent on all the integrated software being secure. Webmail is the worse option for security, because of the use of JS to implement the interface. So long as ONLY the data seen on the network passes through the browser it has no impact on security, other than exploits which open up the whole system.
While a free software mail application is probably safe enough, it only takes an exploit that allows the plain text to be exfiltrated to defeat the use of integrated encryption.
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John Fenderson (profile), 24 Apr 2014 @ 8:33am

Re: Secure E-communications is a gold mine
"Imagine "Secure Google" where you are the customer, not the product. Easily worth $200 a year."

I'm skeptical. You're still relying on third party servers, and if we've learned anything over the past few years, it's that you can't trust third party servers. You still have to take their word for it that it's actually secure. $200 a year for a promise? I don't think that would be worth it to me.
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John Fenderson (profile), 24 Apr 2014 @ 8:37am

Re: Re: Re: Re: This is PR posturing by Google -- don't fall for it
Yup. Probably because he's just plain wrong. For all its faults, and there are many, the lack of competent engineers isn't one of them.

I personally dislike gmail, but to say that it's a clueless service designed by idiots is simply incorrect.
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Anonymous Coward, 24 Apr 2014 @ 8:38am

Re: Re: Re: Re:
The big hole in the browser is the canvas, which is available to most code running in the browser. A secure encryption module serves little purpose if the plain-text can be exfiltrated. Given the Java experience, I would never trust a browser to give the necessary level degree of protection of the plain text.
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John Fenderson (profile), 24 Apr 2014 @ 8:40am

Re: Google encryption
"the more entities like the NSA, FBI, KGB, et. al. will need to PAY GOOGLE for decrypted copies"

If Google has access to decrypted copies at all, then the service isn't secure anyway.
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Anonymous Coward, 24 Apr 2014 @ 11:08am

Re: Re: Secure E-communications is a gold mine
But will this encryption stop Google from their current practice of reading your emails in order to direct advertising to you?

You're aware they do this, right?
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ltlw0lf (profile), 24 Apr 2014 @ 12:59pm

Re: Re: Re: Re: Re:
The big hole in the browser is the canvas, which is available to most code running in the browser. A secure encryption module serves little purpose if the plain-text can be exfiltrated. Given the Java experience, I would never trust a browser to give the necessary level degree of protection of the plain text.

Java, and even JavaScript/ActiveX (which are entirely different languages) are not necessary for a browser. And things like sandboxing, when implemented properly (i.e. not the way Sun/Oracle has done it,) can keep one module from interfering with another.

Canvas access can be blocked and/or protected. In some cases browsers currently protect canvas access between security domains, blocking all access to an encrypted page from an unencrypted frame. It would take some work, but it is not impossible. Throwing the baby out with the bathwater seems tragic, especially when the water is still warm. For paranoid people, the only real way to fix this is to generate locked down, single purpose virtual machines that run a specialized OS and email app, but for the rest of us, the browser is fine so long as the producer of the browser is transparent about what they are doing and smart about security. The biggest problem isn't the browser, but all the malware/spyware installed on the OS anyway.
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Anonymous Coward, 24 Apr 2014 @ 1:00pm

Re: Re: This is PR posturing by Google -- don't fall for it
You say this as if Google doesn't do things like buy a mobile-phone company, get caught red-handed pre-comprimising the underlying operating-system/firmware, and subsequently dump the business once discovered.

http://bit.ly/12dS7Vf
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Anonymous Coward, 24 Apr 2014 @ 1:56pm

Wait. Ladar Levison was able to provide secure service all by himself, while google geeks not.

Maybe there is more to this story?
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John Fenderson (profile), 24 Apr 2014 @ 2:21pm

Re: Re: Re: This is PR posturing by Google -- don't fall for it
That looks Motorola's bad, not Google's. Motorola was doing it before Google bought them.
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Anonymous Coward, 24 Apr 2014 @ 3:31pm

Re: Re: Re: Re: Re: Re:
An email applet in the browser needs some form of scripting, and has access to the canvas where the plain text is displayed, after all it is from that domain, and should allow for unencrypted email. Therefore, for web mail, the plain text is exposed to code not under the users control. A free software separate email program is probably safe, but I would not trust a browser to be able to protect the plain text.
I kinda assumed that anyone worried about security is not running a proprietary OS, or stock Android.
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Anonymous Coward, 24 Apr 2014 @ 3:36pm

Re:
Ladar Levison was able to provide secure service all by himself

Only so long as he was not forced to divulge his keys, and when the keys were he shut the service down and is now in legal trouble. Note he was capable of decoding emails, which is why the government came calling with subpoenas for his keys.
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John Fenderson (profile), 24 Apr 2014 @ 3:45pm

Re: Re: Re: Re: Re: Re: Re:
"I kinda assumed that anyone worried about security is not running a proprietary OS, or stock Android"

Anyone worried about security is not using a webmail system run by a third party in the first place.
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Anonymous Coward, 24 Apr 2014 @ 4:00pm

Re: Re: Re: Re: Re: Re: Re: Re:
So long as encryption is used properly, and you do not need to hide who you are communicating with, it does not matter where the mailbox is located, so long as it connects via SMTP or POP, or if desperate cutting and pasting the encrypted file. All the security in encrypted email lies in protecting the plain text messages and the keys.
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imedia, 25 Apr 2014 @ 12:08am

Encrypted Email
This is good news that Google starting Encrypted Email .
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Anonymous Coward, 25 Apr 2014 @ 1:52am

Re: Re: Re: Re: This is PR posturing by Google -- don't fall for it
Google knew of the practice at acquisition. The end result is still the same - one cannot develop secure clients for pre-compromised operating-systems or hardware. One can only pre-encrypt the communique upon a dedicated disconnected device, then transfer the encrypted end result via safe media to the connected device to subsequently send. It will always be a safe assumption that connected devices are ultimately compromised.
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Anonymous Coward, 25 Apr 2014 @ 2:02am

Re: Re: Re: Re: Re: Re: Re: Re: Re:
Who a person is communicating with is the whole idea behind PRISM. It has been demonstrated ad nausium that knowing who one communicates with can be more important, intelligence-wise, than the content of a particular communication. Obscuring both the content and the recipient is ideal.
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ltlw0lf (profile), 25 Apr 2014 @ 9:44am

Re: Re: Re: Re: Re: Re: Re: Re:
Anyone worried about security is not using a webmail system run by a third party in the first place.

Thanks John... Took the words right out of my mouth.
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ltlw0lf (profile), 25 Apr 2014 @ 10:11am

Re: Re: Re: Re: Re: Re: Re:
An email applet in the browser needs some form of scripting,

I'm sorry, but this isn't true, and never has been true.

An "email applet" might need scripting, but web-mail does not. People have been able to send and receive email from a website without using client-side scripting for a very long time. GMail could provide email capability on their server without providing any javascript, java, or any other client scripting. (Theoretically, they could do the same without server scripting, but it would be a little harder.) The website would look straight out of the 90's, there wouldn't be much in the way of validation, and you wouldn't have much in bells and whistles, but you wouldn't have to worry about client-side scripting security either. Popping up a form to receive text with a submit button would work fine. And you could have a separate third-party application, like GPG, handle the encryption of your email for you.

But all of this is an aside to your argument. Most people use web-mail because they don't want to/can't install third party software on their computer in order to access email. Putting encryption into the web-mail software fixes part of the problem. Would you rather fix part of the problem, or fix none of the problem?
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Mr. Oizo, 25 Apr 2014 @ 11:07am

Blah Google is so great Blah
Mike, mike mike, when the revelation hits the street that Google is the techside of the NSA, at that point many of your posts will look naive and totally out of touch. Just consider for two moments the possibility.

Otherwise, it is a pretty useless article because a- where will the keys be stored (at Google I assume) b- Google still would want to know the decrypted content in order to advertise, making this entire thing just a PR move to gain more trust from the plebs. And making techdirt again a google chill.

Furthermore, the problem with centralized keys has been clearly shown in the lavabit case. If Google can't even tell how many legal requests they get, how will they be able to keep your keys secret ?
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