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> Apple seems to handle this pretty easily with great UX. Sigh. This again. Ok. If have end-to-end encryption, you can't read messages on newly connected devi

> Apple seems to handle this pretty easily with great UX. Sigh. This again. Ok. If have end-to-end encryption, you can't read messages on newly connected devices, unless you somehow pass encryption keys to your new device. If you do not pass keys between devices, and can still read messages sent from other devices, you do not have end-to-end encryption. If the only thing you put into device when connecting is your login/password, then even if Apple does retrieve keys from your device and passes it to new device, it can pass it to themselves and gain access to your super confidential messages. So, no, Apple does not handle this pretty easily. Source: our product has _real_ end-to-end encryption, and it gives the users a rather big amount of discomfort. If you are told you have really secure messenger, but you do not enter anything but your login/password, well, I've got bad news for you. > Which is kind of the point of all these services. If your point is privacy, and you really care about it, just run your own communication server for $2/month. You have all the niceties of server side search and device sync, and none of the pain in the ass that is brought by E2EE. And if your privacy isn't worth $2/month, then you probably don't need E2EE either.

ricardobeat 6y ago
According to docs and endless reporting on iMessage, the messages are end-to-end encrypted in transit. In addition to that, they are stored (optional) in your iCloud account, using a separate key, itself stored in iCloud Keychain (protected by 2FA), and this is how you recover them on a separate device. If you opt-out from iCloud backup the messages are not recoverable, can also set them to be erased after 30 days. > it can pass it to themselves and gain access to your super confidential messages They can also send your PIN, private keys, all logins and passwords to their own servers, or simply log chats from the system keyboard and UI or any of the OS layers they control. The same is true for any app running on iOS/Android. If you don't trust the OS there is no working around it in software.
- Andrew_nenakhov 6y ago
  > According to docs and endless reporting on iMessage, the messages are end-to-end encrypted in transit. According to my rather brief examination of iMessage, you can't verify key fingerprints in iMessage. It means that Apple can install MitM on a probed subject any second, and you would never know that it is there. See: You <-- end-to-end-encryption --> Apple MitM <-- end-to-end-encryption --> Your buddy You have _zero_ control over it, and the only thing keeping your secure and private is Apple's pinky promise. > The same is true for any app running on iOS/Android. Umm, no. There are such things as open source, verifiable builds, and, yes, decentralized messaging protocols. You can take an open source client (for example, from a reputable source like F-droid), and connect to a server totally unrelated to client developer. You can run an encryption protocol where you can actually exchange public keys, verify your keys fingerprints, and confirm the identity of your chat partner. That's what people really concerned with privacy and security do. Others are satisfied with a promise that sounds good enough.
  - ricardobeat 6y ago
    > the only thing keeping your secure and private is Apple's pinky promise Indeed, that's what I meant in the last paragraph. It also means an open source, verified client, with fully secure encryption, is still powerless against the OS capturing keystrokes. You have to rely on that pinky promise either way unless you control the hardware.
    - Andrew_nenakhov 6y ago
      That's true, that's why people who are _really_ paranoid buy special purged phones and flash their own builds of an OS. A friend of mine had a rather successful business selling people such phones.
  - mehrdada 6y ago
    Changing the goal posts? It was about usability of sync/search, now that's addressed, you've brought up the paranoid case of Apple registering an additional device (which only affects messages from on, forward, not the past, mind you, and it is an active attack that can possibly leave a trace if the sending party is looking at the traffic it originates). Sure there are challenges, and the whole point of designing a secure system is to balance various aspects of the system including usability and even politics so that in practice you maximize security for everyone. Apple's choice seems to have been a good one, and it deserves credit for bringing this much security to the masses at precisely zero cognitive burden to the user. Compare it to email, or other popular chat services, for example. But yea, it is correct that you can always prove something cannot be done once you tighten up some mutually exclusive constraints. Question is how much it maps the real world and whether some cannot be loosened.
    - Andrew_nenakhov 6y ago
      Where do you see changing goalposts? First, I started from the obvious truth that apple wasn't the first service that advertised itself as 'secure'. Then I addressed the popular technofetish about the e2ee: people kinda like to feel secure, but are rarely ready to accept all strings that come attached to real security & privacy. You see, e2ee is only practical against the service provider that you have reasons not to trust. But if you don't trust Apple, then you should not trust it all the way to the bottom: and at the bottom we see that iMessage apps give a user zero control over said e2ee. You don't really know who decides your messages on another end: your chat partner or MitM proxy. If you trust Apple that they do not have such proxy, you might as well trust them to not snoop on your chats and store them unencrypted on Apple's servers, saving you from a lot of problem worrying about your keys, devices, etc.

ricardobeat 6y ago

According to docs and endless reporting on iMessage, the messages are end-to-end encrypted in transit. In addition to that, they are stored (optional) in your iCloud account, using a separate key, itself stored in iCloud Keychain (protected by 2FA), and this is how you recover them on a separate device. If you opt-out from iCloud backup the messages are not recoverable, can also set them to be erased after 30 days. > it can pass it to themselves and gain access to your super confidential messages They can also send your PIN, private keys, all logins and passwords to their own servers, or simply log chats from the system keyboard and UI or any of the OS layers they control. The same is true for any app running on iOS/Android. If you don't trust the OS there is no working around it in software.

Andrew_nenakhov 6y ago
> According to docs and endless reporting on iMessage, the messages are end-to-end encrypted in transit. According to my rather brief examination of iMessage, you can't verify key fingerprints in iMessage. It means that Apple can install MitM on a probed subject any second, and you would never know that it is there. See: You <-- end-to-end-encryption --> Apple MitM <-- end-to-end-encryption --> Your buddy You have _zero_ control over it, and the only thing keeping your secure and private is Apple's pinky promise. > The same is true for any app running on iOS/Android. Umm, no. There are such things as open source, verifiable builds, and, yes, decentralized messaging protocols. You can take an open source client (for example, from a reputable source like F-droid), and connect to a server totally unrelated to client developer. You can run an encryption protocol where you can actually exchange public keys, verify your keys fingerprints, and confirm the identity of your chat partner. That's what people really concerned with privacy and security do. Others are satisfied with a promise that sounds good enough.
- ricardobeat 6y ago
  > the only thing keeping your secure and private is Apple's pinky promise Indeed, that's what I meant in the last paragraph. It also means an open source, verified client, with fully secure encryption, is still powerless against the OS capturing keystrokes. You have to rely on that pinky promise either way unless you control the hardware.
  - Andrew_nenakhov 6y ago
    That's true, that's why people who are _really_ paranoid buy special purged phones and flash their own builds of an OS. A friend of mine had a rather successful business selling people such phones.
- mehrdada 6y ago
  Changing the goal posts? It was about usability of sync/search, now that's addressed, you've brought up the paranoid case of Apple registering an additional device (which only affects messages from on, forward, not the past, mind you, and it is an active attack that can possibly leave a trace if the sending party is looking at the traffic it originates). Sure there are challenges, and the whole point of designing a secure system is to balance various aspects of the system including usability and even politics so that in practice you maximize security for everyone. Apple's choice seems to have been a good one, and it deserves credit for bringing this much security to the masses at precisely zero cognitive burden to the user. Compare it to email, or other popular chat services, for example. But yea, it is correct that you can always prove something cannot be done once you tighten up some mutually exclusive constraints. Question is how much it maps the real world and whether some cannot be loosened.
  - Andrew_nenakhov 6y ago
    Where do you see changing goalposts? First, I started from the obvious truth that apple wasn't the first service that advertised itself as 'secure'. Then I addressed the popular technofetish about the e2ee: people kinda like to feel secure, but are rarely ready to accept all strings that come attached to real security & privacy. You see, e2ee is only practical against the service provider that you have reasons not to trust. But if you don't trust Apple, then you should not trust it all the way to the bottom: and at the bottom we see that iMessage apps give a user zero control over said e2ee. You don't really know who decides your messages on another end: your chat partner or MitM proxy. If you trust Apple that they do not have such proxy, you might as well trust them to not snoop on your chats and store them unencrypted on Apple's servers, saving you from a lot of problem worrying about your keys, devices, etc.