So will this bypass prism-like surveillance methods?
Nope.
You can't encrypt the message headers, so the To/From addresses, subject line, sender's IP (usually), and timestamp will all be recoverable.
Mailpile – taking e-mail back
11–20 of 157 posts
Re: Mailpile – taking e-mail back
#12How many times do people have to say this: There is no such thing as secure email. Assume everything is being read. You can't bolt security on (SSL, mailbox encryption, PKI). You have to design it in from the start. SMTP/IMAP etc have crudely hacked on TLS implementations which aren't even guaranteed to be operational site to site. PGP is just an encapsulation which is rarely used. It's a mess. This is just a repacka…
Did you read what Mailpile is doing? Basically making PGP easy to use which solves the lions share of the issues at stake here with the NSA and your complaints.
Yes. Being a bit Theo de Raadt here, but it's a stupid proposition which makes security guarantees that are disingenuous.
a) This assumes that everyone is going to be using Mailpile or something which makes PGP easy to use. This is unrealistic. The moment you fart out an email to gmail, it's useless.
b) this assumes people actually understand PKI. This is unrealistic. Most people can't even manage their own data let alone a mail server hosting environment or a private key securely.
c) Security is still optional. It uses the same insecure protocols as a baseline.
d) It doesn't solve endpoint / mailbox security.
e) There is no technical information or credibility. It's not been field tested, no security reviews have taken place.
f) PGP only encrypts the contents, not the envelope. The envelope is enough to warrant digging out the $5 wrench and whacking you with it until the key appears.
I'm proposing verifiable mandatory protocol level encryption and authentication end to end (MUA to MUA) which is the RIGHT solution. If there is the ability to plausibly deny a message then that's even better (which goes against sender verification so this should be choosable).
The only thing going for it is it looks like a reasonable webmail client (probably better than roundcube)
Re: Mailpile – taking e-mail back
#13How many times do people have to say this: There is no such thing as secure email. Assume everything is being read. You can't bolt security on (SSL, mailbox encryption, PKI). You have to design it in from the start. SMTP/IMAP etc have crudely hacked on TLS implementations which aren't even guaranteed to be operational site to site. PGP is just an encapsulation which is rarely used. It's a mess. This is just a repacka…
Okay, Harry, let us know when you're done with that :-) I suspect most of the rest of us would prefer the perfect not be an enemy of the good.
Re: Mailpile – taking e-mail back
#14 * User-friendly support for both OpenPGP and S/MIME encryption and signatures
* A very fast, scalable search engine
I'd like to know how they achieve both without having the keys, and without shipping code (JS, java applet) that has access to the keys.
Also, excuse my lack of trust, but why should I trust a SaaS created by a Google employee, as opposed to trusting a SaaS created by Google ? That makes no sense to me.
If you're worried about privacy, store your own emails. Period.
Re: Mailpile – taking e-mail back
#15How many times do people have to say this: There is no such thing as secure email. Assume everything is being read. You can't bolt security on (SSL, mailbox encryption, PKI). You have to design it in from the start. SMTP/IMAP etc have crudely hacked on TLS implementations which aren't even guaranteed to be operational site to site. PGP is just an encapsulation which is rarely used. It's a mess. This is just a repacka…
Silly question: If you can trust DNS, and require every client to connect to an SMTP server with TLS/SSL, and only permit SMTP server->SMTP server connections over SSL, how does that not fix the problem?
End to end encryption and MITM countermeasures should solve the issue, no? Then all the NSA knows is which mail server is talking to which mail server.
I admit, I could be very wrong. Please tell me why.
Re: Mailpile – taking e-mail back
#16How many times do people have to say this: There is no such thing as secure email. Assume everything is being read. You can't bolt security on (SSL, mailbox encryption, PKI). You have to design it in from the start. SMTP/IMAP etc have crudely hacked on TLS implementations which aren't even guaranteed to be operational site to site. PGP is just an encapsulation which is rarely used. It's a mess. This is just a repacka…
Okay, Harry, let us know when you're done with that :-) I suspect most of the rest of us would prefer the perfect not be an enemy of the good.
I have no desire to solve the problem. If I wanted to be an evil terrorist and blow shit up, which I don't, I'd quite happily do it without communicating with people.
As for good, it's not even that. See my comment here: https://news.ycombinator.com/item?id=6244196
Also, bear in mind I had the unfortunate job of designing and running ISP mail systems for a number of years so I know the whole stack inside out.
Re: Mailpile – taking e-mail back
#17Earlier quoted context omitted.
Did you read what Mailpile is doing? Basically making PGP easy to use which solves the lions share of the issues at stake here with the NSA and your complaints.
Yes. Being a bit Theo de Raadt here, but it's a stupid proposition which makes security guarantees that are disingenuous. a) This assumes that everyone is going to be using Mailpile or something which makes PGP easy to use. This is unrealistic. The moment you fart out an email to gmail, it's useless. b) this assumes people actually understand PKI. This is unrealistic. Most people can't even manage their own data let…
Exactly this. Mailpile sounds like a good idea in principle until you start looking at the underlying tech. They explicitly say they will not be implementing a MTA. Since an eavesdropper knows who youre sending to and what the subjects are youre a bit vulnerable to a literal brute force attack: http://xkcd.com/538/
Re: Mailpile – taking e-mail back
#18I would like to mention that the details of this project seem a little sparse. For a truly secure solution, this system will need to (1) define a secure standard and (2) allow domain owners to personally host this system which can connect to legacy mail servers as well as the "new" secure standard. This way, when persons communicate within the same email domain and between secure systems, the communication can be considered secure.
Just my 2 cents I guess.
A system like this can succeed, but I think it's too early to judge.
Re: Mailpile – taking e-mail back
#19Earlier quoted context omitted.
Did you read what Mailpile is doing? Basically making PGP easy to use which solves the lions share of the issues at stake here with the NSA and your complaints.
Yes. Being a bit Theo de Raadt here, but it's a stupid proposition which makes security guarantees that are disingenuous. a) This assumes that everyone is going to be using Mailpile or something which makes PGP easy to use. This is unrealistic. The moment you fart out an email to gmail, it's useless. b) this assumes people actually understand PKI. This is unrealistic. Most people can't even manage their own data let…
It seems to me the mailpile people are quite aware of what they are building and do not oversell their product. They even talk of risk assessment right in the indiegogo webpage.
Regarding your points: a-d) I assume that mailpile to mailpile communications will be PGP armed by default. It's enough for them to clear this unambiguously (for instance with a STAR next to "secure" addresses or a popup that says "you are sendind a message to a gmail account, be aware that...)
e) alright
f) there are other quite trivial ways to protect identities, such as a pen-name and a starbucks connection. Those are quite useless, however, if the message is not encrypted.
Re: Mailpile – taking e-mail back
#20How many times do people have to say this: There is no such thing as secure email. Assume everything is being read. You can't bolt security on (SSL, mailbox encryption, PKI). You have to design it in from the start. SMTP/IMAP etc have crudely hacked on TLS implementations which aren't even guaranteed to be operational site to site. PGP is just an encapsulation which is rarely used. It's a mess. This is just a repacka…
Silly question: If you can trust DNS, and require every client to connect to an SMTP server with TLS/SSL, and only permit SMTP server->SMTP server connections over SSL, how does that not fix the problem? End to end encryption and MITM countermeasures should solve the issue, no? Then all the NSA knows is which mail server is talking to which mail server. I admit, I could be very wrong. Please tell me why.
Well (E)SMTP works effectively by connecting, then knocking on the door and asking for a list of capabilities (EHLO). When the remote SMTP server says "no I don't support TLS", what are you supposed to do?
Email only works at the moment because in this scenario, usually the sending MTA just says "what the hell" and delivers it over the wire in plain text anyway.
The moment you force TLS as a requirement, the internet starts having lots of large black holes in it due to the number of SMTP servers that don't support it (still) or don't have valid certificates. At that point email fails.
However, the moment you agree to it, you are at the mercy of the root PKI (certificate authorities) who aren't necessarily all that trustworthy. Any fucker can buy an SSL certificate and masquerade as someone else. Also don't forget that CRL (revocation lists) exist that list naff CA certs that have been compromised. At that point, encryption fails.
That's why it's fucked - whack-a-mole all over the place.