6 ms·

The 99.9% freak me out. The huge problem with email encryption right now is that you can't reasonably make it mandatory (as you can see, a lots of domain do no

The 99.9% freak me out. The huge problem with email encryption right now is that you can't reasonably make it mandatory (as you can see, a lots of domain do not support it) so it can be easily be stripped à la sslstrip, and there is no such a thing as HSTS. (Again, please, build pinning into everything.) So an active attacker able to MitM can simply turn encryption off, and those 99.9% make me wonder if that happened to the 0.1%...

magicalist 12y ago
> The huge problem with email encryption right now is that you can't reasonably make it mandatory Many services can make it mandatory, as long as you're willing to take the hit to convenience, so at least your outbound email is always protected (and you get some level of canary for inbound email). This is usually for some compliance rule or another because they want enterprise business, so even the mainstream ones like Google Apps[1] and Office 365[2] have support for requiring TLS. [1] https://support.google.com/a/answer/2520500?hl=en https://support.google.com/a/answer/2520500?hl=en [2] http://technet.microsoft.com/en-US/library/jj723154%28v=exchg.150%29.aspx http://technet.microsoft.com/en-US/library/jj723154%28v=exch...
7952 12y ago
That problem is quite common on the internet in general. Just think how common ftp still is! We constantly use public networks and then have to mitigate the fact that the packets are public. It would be better to treat encryption like a peering arrangement. When there is sufficient traffic between two large networks all packets should be routed via an encrypted tunnel.
- Tiksi 12y ago
  While I generally agree with the concept, encryption isn't free, and will break pretty much every routing protocol used. It's easy enough to get a tunnel through transit when you control both ends, but neither the hardware nor the software that actually runs the peers supports it in any way. You'd have to set the link, then encrypt on top of that, costing a ton of cpu cycles, bandwidth overhead, and requiring something that can handle encrypting everything in real time and then pass it off to the actual edge connection. "Large" networks do 100Gbit plus, and I can't think of any way this is currently feasible to do.
  - 7952 12y ago
    I was really thinking in terms of coporate networks, which would be considered small. It is already common on such networks to have proxies/NAT/filtering that inspect and route everything in a very resource unfrinedly way. I would propose creating single VPN tunnel between these corporate networks that all traffic destined for the other network is routed down. Just join individual private networks with encryped tiunnels. This would be completely transparent at the client level as the data would just follow a different path. It would avoid the startup cost of SSL or the higher CPU requirements of symmetric encryption. Such a setup could be required as a contract/tendering/supplier requirement. Really if you have two companies that are sending data that may be sensitive why would you want any of the packets to ever be sent in plan view? Client side standards will never give a complete gurantee of that. It is much more enforcable to add the security at the network level.
higherpurpose 12y ago
STARTTLS seems to work like that joke in Anchorman: It works 60 percent of the time...every time.
- FiloSottile 12y ago
  Worse, it works 100%... 99.9% of the times. The other times, it's when someone wants it not to work.
  - lugg 12y ago
    My guess is dem pesky 99.9% sla's and routing around the downtime in some way.
lugg 12y ago
> The huge problem with email encryption right now is that you can't reasonably make it mandatory Sure you can, see pgp. Really, its nice to see they are encrypting coms between each other but I don't really see how this affects me. If I want something secure I will use pgp. Email encryption, has and, always will be a client side problem. There is nothing the middle men and women can do for you that you can reasonably trust. If google really wants to solve this problem they will make pgp features native to gmail. I'm guessing they're heading that way with the chrome extension being discussed here at the minute[1]. [1] https://news.ycombinator.com/item?id=7842696 https://news.ycombinator.com/item?id=7842696
- phkahler 12y ago
  But Google likes to read your email so they can target ads. Even they don't want you to encrypt on the client.
  - judk 12y ago
    Don't want and don't support are two different things. Google have lots of ways to get ad signal.
  - lugg 12y ago
    Leading the way looks a lot better than dragging your feet on something that is going to happen whether they want it to or not. At least they can say "hey we lead the way on this, even if it was 3 decades too late"
    - tcheard 12y ago
      > that is going to happen whether they want it to or not I highly doubt this. This sounds like wishful thinking.
      - lugg 12y ago
        Pessimism, just as illogical as optimism. As in, care to explain why you so highly doubt it? I have little more than anecdotal trends as evidence.
SilasX 12y ago
But email providers don't need end user cooperation to implement intra-provider encryption, i.e. encryption of intermediate hops before it's finally read. (If you email another gmail user, Google can keep the whole voyage encrypted, and likewise if you email a Yahoo user after they agree to encrypt email between the services.) Yes, such schemes are leaky, as they allow the attacker to read it at any link between providers that haven't cooperated to set up a secure link. And it probably doesn't change the "expectation of privacy" issue, as the provider will be applying encryption to the plaintext, but it decreases the attack surface without requiring end user action.

magicalist 12y ago

> The huge problem with email encryption right now is that you can't reasonably make it mandatory Many services can make it mandatory, as long as you're willing to take the hit to convenience, so at least your outbound email is always protected (and you get some level of canary for inbound email). This is usually for some compliance rule or another because they want enterprise business, so even the mainstream ones like Google Apps[1] and Office 365[2] have support for requiring TLS. [1] https://support.google.com/a/answer/2520500?hl=en https://support.google.com/a/answer/2520500?hl=en [2] http://technet.microsoft.com/en-US/library/jj723154%28v=exchg.150%29.aspx http://technet.microsoft.com/en-US/library/jj723154%28v=exch...

7952 12y ago

That problem is quite common on the internet in general. Just think how common ftp still is! We constantly use public networks and then have to mitigate the fact that the packets are public. It would be better to treat encryption like a peering arrangement. When there is sufficient traffic between two large networks all packets should be routed via an encrypted tunnel.

Tiksi 12y ago
While I generally agree with the concept, encryption isn't free, and will break pretty much every routing protocol used. It's easy enough to get a tunnel through transit when you control both ends, but neither the hardware nor the software that actually runs the peers supports it in any way. You'd have to set the link, then encrypt on top of that, costing a ton of cpu cycles, bandwidth overhead, and requiring something that can handle encrypting everything in real time and then pass it off to the actual edge connection. "Large" networks do 100Gbit plus, and I can't think of any way this is currently feasible to do.
- 7952 12y ago
  I was really thinking in terms of coporate networks, which would be considered small. It is already common on such networks to have proxies/NAT/filtering that inspect and route everything in a very resource unfrinedly way. I would propose creating single VPN tunnel between these corporate networks that all traffic destined for the other network is routed down. Just join individual private networks with encryped tiunnels. This would be completely transparent at the client level as the data would just follow a different path. It would avoid the startup cost of SSL or the higher CPU requirements of symmetric encryption. Such a setup could be required as a contract/tendering/supplier requirement. Really if you have two companies that are sending data that may be sensitive why would you want any of the packets to ever be sent in plan view? Client side standards will never give a complete gurantee of that. It is much more enforcable to add the security at the network level.

higherpurpose 12y ago

STARTTLS seems to work like that joke in Anchorman: It works 60 percent of the time...every time.

FiloSottile 12y ago
Worse, it works 100%... 99.9% of the times. The other times, it's when someone wants it not to work.
- lugg 12y ago
  My guess is dem pesky 99.9% sla's and routing around the downtime in some way.

lugg 12y ago

> The huge problem with email encryption right now is that you can't reasonably make it mandatory Sure you can, see pgp. Really, its nice to see they are encrypting coms between each other but I don't really see how this affects me. If I want something secure I will use pgp. Email encryption, has and, always will be a client side problem. There is nothing the middle men and women can do for you that you can reasonably trust. If google really wants to solve this problem they will make pgp features native to gmail. I'm guessing they're heading that way with the chrome extension being discussed here at the minute[1]. [1] https://news.ycombinator.com/item?id=7842696 https://news.ycombinator.com/item?id=7842696

phkahler 12y ago
But Google likes to read your email so they can target ads. Even they don't want you to encrypt on the client.
- judk 12y ago
  Don't want and don't support are two different things. Google have lots of ways to get ad signal.
- lugg 12y ago
  Leading the way looks a lot better than dragging your feet on something that is going to happen whether they want it to or not. At least they can say "hey we lead the way on this, even if it was 3 decades too late"
  - tcheard 12y ago
    > that is going to happen whether they want it to or not I highly doubt this. This sounds like wishful thinking.
    - lugg 12y ago
      Pessimism, just as illogical as optimism. As in, care to explain why you so highly doubt it? I have little more than anecdotal trends as evidence.

SilasX 12y ago

But email providers don't need end user cooperation to implement intra-provider encryption, i.e. encryption of intermediate hops before it's finally read. (If you email another gmail user, Google can keep the whole voyage encrypted, and likewise if you email a Yahoo user after they agree to encrypt email between the services.) Yes, such schemes are leaky, as they allow the attacker to read it at any link between providers that haven't cooperated to set up a secure link. And it probably doesn't change the "expectation of privacy" issue, as the provider will be applying encryption to the plaintext, but it decreases the attack surface without requiring end user action.