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The Sinking Ship of E-Mail Security

adamcaudill.com

21–30 of 56 posts

Re: The Sinking Ship of E-Mail Security

#21

Ok, I'll bite. This is a good post - I am negative on your ability to pull this off, but it's a worthwhile discussion to have IMO * Totally anonymous (ie no metadata trail) communication seems impossible / impractical. If everywhere is the Tor then we massively increase traffic, (not to mention the trustworthiness of "everyone" is a lot lower per unit than everyone currently running a tor node) Anyway, even if a encr…

K-9 mail on Android. Not sure about iOS, but I have seen an implementation somewhere on code.google in the past (not sure of its current status).

K-9 Mail is good, but it doesn't support PGP/MIME. Only inline PGP. Doesn't look like they will either as it's been on their todo list for several years now with no progress.

Re: The Sinking Ship of E-Mail Security

#22
post #4

Mobile - Using PGP on a mobile device can be risky, as it requires storing the private key on devices that are likely to have known security issues. Many people recommend against it, as it puts the private key at too much risk. ARGH. The whole point of PGP keyrings --- the costliest part of the PGP UX --- is that you don't have to have a single key. If you're terrified of exposing your secret key on your mobile devic…

> which is frankly the most secure device you own

Really? That's not how I treat my security at all. My phone seems to clearly be the least secure computer I own. Admittedly I run all linux on my non-phone computers, but I'm not totally sure I'd agree with you even if I ran Windows or OSX.

Am I that wrong?

Re: The Sinking Ship of E-Mail Security

#23

Earlier quoted context omitted.

K-9 mail on Android. Not sure about iOS, but I have seen an implementation somewhere on code.google in the past (not sure of its current status).

K-9 Mail is good, but it doesn't support PGP/MIME. Only inline PGP. Doesn't look like they will either as it's been on their todo list for several years now with no progress.

Whilst this is true it is not really that big a problem. You can open the attachment, copy to the clipboard and then use APG to decrypt. It could be nicer and would be excellent if the client supported PGP/MIME, but I can live with it.

Re: The Sinking Ship of E-Mail Security

#25

Ok, I'll bite. This is a good post - I am negative on your ability to pull this off, but it's a worthwhile discussion to have IMO * Totally anonymous (ie no metadata trail) communication seems impossible / impractical. If everywhere is the Tor then we massively increase traffic, (not to mention the trustworthiness of "everyone" is a lot lower per unit than everyone currently running a tor node) Anyway, even if a encr…

> Totally anonymous (ie no metadata trail) communication seems impossible / impractical. If everywhere is the Tor then we massively increase traffic

That really isn't the problem. If onion routing works for anything it works for email. Text is low bandwidth. You make the email servers relay for each other so it scales: More email servers, more relays. And if you're willing to have your emails delayed by e.g. half an hour you can get a much stronger level of anonymity than you can with realtime systems like Tor because random delays between hops on high traffic nodes in combination with padding to power-of-two size boundaries makes traffic analysis extremely difficult.

> Anyway, even if a encrypted anonymous message arrives for me, just working out who it's from without any metadata seems complex web of double decryption

Every message to you should be encrypted against your public key, so you decrypt it with your private key and immediately learn who it's from. The issue is if you have multiple public keys and you don't want the message to identify which one to use in any way. There could be some interesting cryptographic solutions to that I'm not aware of, although in the worst case you could just try all of them until one works.

Re: The Sinking Ship of E-Mail Security

#26

Ok, I'll bite. This is a good post - I am negative on your ability to pull this off, but it's a worthwhile discussion to have IMO * Totally anonymous (ie no metadata trail) communication seems impossible / impractical. If everywhere is the Tor then we massively increase traffic, (not to mention the trustworthiness of "everyone" is a lot lower per unit than everyone currently running a tor node) Anyway, even if a encr…

I'm not the only one working on it, but I am the lead. I have my doubts too - but I don't see that as an issue. Any email replacement has a long way to go before it would be used widely - getting a real standard through the IETF alone will be difficult. But, this is a starting point - it's something to build from, a conversation starter if nothing else. Even if it gets ripped to shreds, if it gets people actively working on another solution, then it was worth it.

It's the conversion that matters to me, there needs to be a solution to this, and for that to happen people need to get engaged.

As for anonymity, I don't think there's a good option there - the spec I'm writing isn't anonymous to the recipient, or to the recipient's server. My focus is on encryption and authentication. There's more metadata exposed than I'd like in my model, but it's a balancing act between competing goals. We'll see that in any standard that replaces email - there are many forces at play with different goals and different requirements. No solution will make everyone happy.

There are issues, metadata being a big one, that the proposal I'm working one doesn't address as well as I'd like. I'm hoping others will try to tackle this issue as well, and come up with other methods that may work better.

When we are ready to release a public draft, it'll just be the first step. We don't expect anyone to just say "Hey, that's perfect, let's replace all the email servers" - that isn't going to happen, and it's not our goal. A lot of review will be needed, changes will need to be made to address different concerns, and maybe it'll progress to a useful system. Maybe somebody else will come along with a different idea, and that one will get the community backing. What I want is a replacement system that is secure - I don't care who's design it is. It's not about ego, not about winning for me - it's about prodding the community into action.

As to the last question, as others have answered, K-9 Mail. It works well enough for my needs.

Re: The Sinking Ship of E-Mail Security

#28
post #10

Earlier quoted context omitted.

How much does it matter if you lose your encrypted PGP keyring on your fully-encrypted smartphone in a bad part of town?

The same as any other device. I'm nitpicking.

It depends on the device, I guess, but no, I'm saying your phone is better off in that scenario than any of your other devices.

Re: The Sinking Ship of E-Mail Security

#29
post #4

Mobile - Using PGP on a mobile device can be risky, as it requires storing the private key on devices that are likely to have known security issues. Many people recommend against it, as it puts the private key at too much risk. ARGH. The whole point of PGP keyrings --- the costliest part of the PGP UX --- is that you don't have to have a single key. If you're terrified of exposing your secret key on your mobile devic…

> which is frankly the most secure device you own Really? That's not how I treat my security at all. My phone seems to clearly be the least secure computer I own. Admittedly I run all linux on my non-phone computers, but I'm not totally sure I'd agree with you even if I ran Windows or OSX. Am I that wrong?

Considering how locked down they are (iPhone, at least), yes, they are likely substantially more secure than PCs for most people.

Re: The Sinking Ship of E-Mail Security

#30
post #29

Earlier quoted context omitted.

> which is frankly the most secure device you own Really? That's not how I treat my security at all. My phone seems to clearly be the least secure computer I own. Admittedly I run all linux on my non-phone computers, but I'm not totally sure I'd agree with you even if I ran Windows or OSX. Am I that wrong?

Considering how locked down they are (iPhone, at least), yes, they are likely substantially more secure than PCs for most people.

You have to be more specific: Secure from what kind of threat? There are many threats ranging from service providers deciding to uninstall "unpopular" applications that threaten antiquated revenue models to State threats used against activists and dissidents.
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