The Sinking Ship of E-Mail Security • Hacker News Board

Re: The Sinking Ship of E-Mail Security

#11

Post by dredmorbius » Sat, Jun 28, 2014, 9:37 PM UTC

tptacek wrote: 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…

The challenge here is that you've then got to get other people to use the appropriate PGP key(s).

If a key has multiple subkeys, are they all used in encrypting a given message?

That's an aspect of PGP/GPG use I'm not clear on despite >15 years use of it.

Re: The Sinking Ship of E-Mail Security

#12

Post by jiggy2011 » Sat, Jun 28, 2014, 10:04 PM UTC

tptacek wrote: post #10

jiggy2011 wrote: post #9

Earlier quoted context omitted.

> If you're terrified of exposing your secret key on your mobile device (which is frankly the most secure device you own), just cut a new key for it. The mobile device is the one most people have the least control over in terms of software (which can be both good and bad) but is also the one they are most likely to lose in a shady part of town. I agree with the rest of your post though.

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.

Re: The Sinking Ship of E-Mail Security

#13

Post by mike-cardwell » Sat, Jun 28, 2014, 10:10 PM UTC

dredmorbius wrote: post #11

tptacek wrote: 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…

The challenge here is that you've then got to get other people to use the appropriate PGP key(s). If a key has multiple subkeys, are they all used in encrypting a given message? That's an aspect of PGP/GPG use I'm not clear on despite >15 years use of it.

Depends on the implementation. GnuPG picks the most recently created encryption subkey and uses that one. It doesn't use both. Not by default anyway.

Re: The Sinking Ship of E-Mail Security

#14

Post by [deleted] » Sat, Jun 28, 2014, 10:36 PM UTC

0xeeeeeeee wrote: post #2

Email security is really bad. We have a lot of companies trying to roll out "secure email" every week. There are a ton of problems to solve before one of these actually works, javascript crypto being the least (since HN likes to discuss it...). Backwards compatibility with old email protocols and insecure service is clearly a weak-link in any hypothetically secure service. It would be nice to see a more distributed p…

[deleted]

Re: The Sinking Ship of E-Mail Security

#15

Post by lifeisstillgood » Sat, Jun 28, 2014, 10:37 PM UTC

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

I do struggle with how anonymity is going to solve all problems with totalitarian states. In the end we need to solve this in the real world of politics and execution squads so we don't mortally worry about letters or emails being read.

* there is a lot more here than my tired brain can handle - but my main concern is a simple human one

- if secure anonymous comms is "impossible", then I could see levels of secure encryption (sent from my iPhone, sent from my PC hardwired at home that has a secure USB boot on my key ring). But this idea demands that as the recipient I work hard to determine from context if the message is secure - aha it's 11pm in the UK and Adam just mailed me a secure note saying we should give everyone an Owl. Chances are high he is pissed and his mates sent it.

Once technology stops helping us make those decisions it's kind of pointless - May as well just keep sending clear text is not an irrational stance.

Be interested in the discussion in the morning - cheers

* lastly - what email client do you guys use that allows gpg on mobile?!

Edit: clean up

Re: The Sinking Ship of E-Mail Security

#16

Post by narrowrail » Sat, Jun 28, 2014, 10:45 PM UTC

lifeisstillgood wrote: post #15

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).

Re: The Sinking Ship of E-Mail Security

#17

Post by ams6110 » Sat, Jun 28, 2014, 10:46 PM UTC

I think of email like a postcard. It's addressed to me, but anyone can read it if they snoop in my mailbox. I don't expect it to be really secure, and I don't do anything that requires real security via email. Simple enough.

Re: The Sinking Ship of E-Mail Security

#18

Post by lifeisstillgood » Sat, Jun 28, 2014, 10:49 PM UTC

narrowrail wrote: post #16

lifeisstillgood wrote: post #15

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).

Thanks - am looking to jump to the dark side soon anyway :-)

Re: The Sinking Ship of E-Mail Security

#19

Post by leeoniya » Sat, Jun 28, 2014, 10:51 PM UTC

ams6110 wrote: post #17

I think of email like a postcard. It's addressed to me, but anyone can read it if they snoop in my mailbox. I don't expect it to be really secure, and I don't do anything that requires real security via email. Simple enough.

what arrives in your inbox is often out of your control. account confirmation and password reset emails, pictures/info others send you who are more satisfied that you with the level of privacy normal email provides, etc.

Re: The Sinking Ship of E-Mail Security

#20

Post by htns » Sat, Jun 28, 2014, 11:12 PM UTC

I would suggest taking a look at I2P-Bote. Although I haven't had it installed for a year at least, I2P-bote seems to be a slow-moving project, with lots of features TBD, but it does hit all the keywords.