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I feel like client-side email encryption is a missed opportunity for Apple. Easy encrypted email would fit nicely into their narrative of “we can offer privacy

I feel like client-side email encryption is a missed opportunity for Apple. Easy encrypted email would fit nicely into their narrative of “we can offer privacy features that Google can’t, because we sell you stuff”

y4mi 9y ago
Encryption doesn't work unless both sides use it. Apple supporting it won't help apple users one bit, because nobody else uses an actual application to check mails anymore. It's mostly web mail clients everywhere, and they obviously can't use encryption.
- kahnpro 9y ago
  iMessage?
  - jayd16 9y ago
    Apple controls all sides of iMessage.
- peatmoss 9y ago
  iOS? Plus, I know folks who use mail.app. I also bet they could figure out how to instrument Safari with browser-side encryption for their cloud users. A few more privacy scandals break, and if Apple had an end-to-end encryption story that sounds roughly like: “If you’re using Apple products and services, you probably don’t need to think too much about the techy parts.” I could easily see Apple cementing their position for anyone even remotely concerned about privacy. Apple the computer company. Apple the media company. Apple the smartphone conpany. Apple the consumer privacy and protection company? I could see it.
  - virusduck 9y ago
    Where do you keep the keys? * On the device? Oops--device broke, guess my emails are gone forever * In the "cloud"? -- Oops, can't guarantee encryption Who generated the keys and how do you build trust? For both of these, you can trust Apple do do the right thing, but that's putting all your eggs into that basket, similar to iMessage.
    - Spivak 9y ago
      On device with the key exportable and optionally escrowed to iCloud. Key management isn't exactly an unsolved problem.
      - y4mi 9y ago
        > Key management isn't exactly an unsolved problem you're right its not an unsolved problem, its an unsolvable problem. There is little point in encrypting mails between apple users, if the keys are kept on the apple servers. What would it achieve after all? Apple, and by extension every nation of importance would still have access. the only reward you'd get from that is getting locked into the apple ecosphere even stronger, because now you won't be able to read your mail archive anymore unless you use an apple device. And you obviously can kiss search goodbye. There is no way to search encrypted data after all, unless you decrypt it.
- aylmao 9y ago
  Would be interesting if they built something like SMS/iMessage, where within the ecosystem emails were encrypted but when sent outside they weren't. Of course, hopefully PGP, and not some custom, private API like iMessage.
  - JonathonW 9y ago
    If you're looking for an "open ecosystem" option, Mail on both iOS and Mac (as well as a bunch of clients elsewhere, including Outlook and Thunderbird) supports S/MIME encryption and signing out of the box. Of course, no one uses it or even realizes it's there because S/MIME is terrible.
    - hedora 9y ago
      Actually, with let’s encrypt and friends, maybe it is finally time for s/mime (with cert pinning, web of trust for the paranoid)
- blowski 9y ago
  > nobody else uses an actual application to check mails anymore Got any data to back that up? I do, and so do a lot of my friends and colleagues.
  - dingaling 9y ago
    Indeed the vast majority of people I know use a MUA program to access their e-mail. They're just called 'apps' nowadays.
bluGill 9y ago
Useful client side encryption is hard. If the user doesn't understand what they are doing feel like they have security when in reality any script kiddie can break their encryption.
- peatmoss 9y ago
  iMessage ain’t Signal, but it’s also better than the default posture of email.
Mister_Snuggles 9y ago
Apple already does this[0]. However, this relies on users creating and managing certificates and keys, which is not an easy thing for most users. I was playing around with using my own CA to issue certificates for internal stuff. I created a personal certificate for myself and imported it to my keychain - without doing anything, Apple Mail was digitally signing my messages. On the other side, however, people saw digital signatures that couldn't be verified and got confused by that. [0] https://support.apple.com/en-ca/guide/mail/sign-encrypt-messages-increased-security-mlhlp1180/mac https://support.apple.com/en-ca/guide/mail/sign-encrypt-mess...
woolvalley 9y ago
They already have, it's called iMessage ;)

y4mi 9y ago

Encryption doesn't work unless both sides use it. Apple supporting it won't help apple users one bit, because nobody else uses an actual application to check mails anymore. It's mostly web mail clients everywhere, and they obviously can't use encryption.

kahnpro 9y ago
iMessage?
- jayd16 9y ago
  Apple controls all sides of iMessage.
peatmoss 9y ago
iOS? Plus, I know folks who use mail.app. I also bet they could figure out how to instrument Safari with browser-side encryption for their cloud users. A few more privacy scandals break, and if Apple had an end-to-end encryption story that sounds roughly like: “If you’re using Apple products and services, you probably don’t need to think too much about the techy parts.” I could easily see Apple cementing their position for anyone even remotely concerned about privacy. Apple the computer company. Apple the media company. Apple the smartphone conpany. Apple the consumer privacy and protection company? I could see it.
- virusduck 9y ago
  Where do you keep the keys? * On the device? Oops--device broke, guess my emails are gone forever * In the "cloud"? -- Oops, can't guarantee encryption Who generated the keys and how do you build trust? For both of these, you can trust Apple do do the right thing, but that's putting all your eggs into that basket, similar to iMessage.
  - Spivak 9y ago
    On device with the key exportable and optionally escrowed to iCloud. Key management isn't exactly an unsolved problem.
    - y4mi 9y ago
      > Key management isn't exactly an unsolved problem you're right its not an unsolved problem, its an unsolvable problem. There is little point in encrypting mails between apple users, if the keys are kept on the apple servers. What would it achieve after all? Apple, and by extension every nation of importance would still have access. the only reward you'd get from that is getting locked into the apple ecosphere even stronger, because now you won't be able to read your mail archive anymore unless you use an apple device. And you obviously can kiss search goodbye. There is no way to search encrypted data after all, unless you decrypt it.
aylmao 9y ago
Would be interesting if they built something like SMS/iMessage, where within the ecosystem emails were encrypted but when sent outside they weren't. Of course, hopefully PGP, and not some custom, private API like iMessage.
- JonathonW 9y ago
  If you're looking for an "open ecosystem" option, Mail on both iOS and Mac (as well as a bunch of clients elsewhere, including Outlook and Thunderbird) supports S/MIME encryption and signing out of the box. Of course, no one uses it or even realizes it's there because S/MIME is terrible.
  - hedora 9y ago
    Actually, with let’s encrypt and friends, maybe it is finally time for s/mime (with cert pinning, web of trust for the paranoid)
blowski 9y ago
> nobody else uses an actual application to check mails anymore Got any data to back that up? I do, and so do a lot of my friends and colleagues.
- dingaling 9y ago
  Indeed the vast majority of people I know use a MUA program to access their e-mail. They're just called 'apps' nowadays.

bluGill 9y ago

Useful client side encryption is hard. If the user doesn't understand what they are doing feel like they have security when in reality any script kiddie can break their encryption.

peatmoss 9y ago
iMessage ain’t Signal, but it’s also better than the default posture of email.

Mister_Snuggles 9y ago

Apple already does this[0]. However, this relies on users creating and managing certificates and keys, which is not an easy thing for most users. I was playing around with using my own CA to issue certificates for internal stuff. I created a personal certificate for myself and imported it to my keychain - without doing anything, Apple Mail was digitally signing my messages. On the other side, however, people saw digital signatures that couldn't be verified and got confused by that. [0] https://support.apple.com/en-ca/guide/mail/sign-encrypt-messages-increased-security-mlhlp1180/mac https://support.apple.com/en-ca/guide/mail/sign-encrypt-mess...

woolvalley 9y ago

They already have, it's called iMessage ;)