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That's what GPGTools is for (formally MacGPG): https://gpgtools.org/opensource.html https://gpgtools.org/opensource.html (You can build and use your own gpg bi

by aroch 11y ago

That's what GPGTools is for (formally MacGPG): https://gpgtools.org/opensource.html https://gpgtools.org/opensource.html (You can build and use your own gpg binaries if you're concerned about their modifications)

nailer 11y ago
GPGTools is precisely the awful state of current of affairs I'm talking about. - GPGTools isn't sure what's called. GPGTools? OK where do I download GPGTools? There's no button to do that. What's GPGSuite? Do I want that instead? Installed, there's nothing called either Applications/GPGTools or Applications/GPG Suite. - Its app is called 'GPG keychain' or similar. Nobody outside crypto folk care know what a keychain or, not should knowledge of a keychain app be required to send someone a message encrypted with their public key - The apps main focus is key management, and it's really poor at that. There's no way to discover people's GPG keys AFAICT - It's a plugin for Apple Mail and a command line app. Most people using Macs don't use either of those. And it's not promoted as a Mac mail plugin, which means most people will be disappointed when they use it. - It seems to choke on common GPG output with some chars. That output is probably not encoded correctly, that shouldn't matter. Be liberal in what you accept.
- aroch 11y ago
  1) If installing something is enough of a hurdle that you can't complete it, then no amount of simplification beyond bundling is going to solve that 2) Everyone and their mother understand that keychains hold keys. You have to get to a key somehow, the onboarding process is a simple wizard. Again, if you can't follow prompts to enter an email, enter a password, and wiggle your mouse around; no amount of simplification is going to solve the problem. 3) You use the search for key button... 4) I'd argue that the vast majority of Mac users, especially the ones that are not technically inclined enough to use GPG on cli but want to, use the built in Mail.app. 5) gpg seems to have a slew of text encoding gotchas, I'm not sure how those can be fixed without a lot of core dev effort
  - oceanofsolaris 11y ago
    I think that your points 2) and 3) are not perfectly reasonable if you really want to reach those who are not yet using encryption. If you look at how keychains are usually used nowadays, they are an implementation detail you could and probably should hide from non-technical users. As you say yourself, in order to find a key, you use the search for key button. Which prompts the program to look on a keyserver. You then import the first non-expired key you find for the desired email address. Why not do this automatically? You just annoy users who have to go through two (highly non-self-evident) steps and who do neither know nor care what a 'key' is. They just want to write secure email to their friends. (and btw, does the key-search even go over a secure connection with a pinned certificate? Because else you are not even trying to avoid MITM attacks). Is it too much to ask these users to read the manual, learn about which kind of key is the most secure yet also compatible with the GPG versions of their friends, find out how many bits theirs should have, have them wiggle their mouse (why, couldn't you use /dev/urandom for most cases?), upload their key to a keyserver, search their friends key from a keyserver, learn about the web of trust and go to a key-signing party? Is this too much to ask? Probably yes. I did not need to acquire a similar amount of knowledge about TextSecure and yet it probably transmits my messages in a more secure form than GPG. I am not saying that key-discovery is super-easy and all these are completely solved problems. But why do you have to make it so much more complicated for users than it has to be?
    - aroch 11y ago
      PGP is not supposed to be TOFU, friction to adding/trusting keys is part of the point of PGP -- verification of trust. If clicking a prominently placed button to lookup a key is not intuitive, then how do these users manage the just as unintuitive process of finding, verifying, and installing an application on their device? Keys are searchable over HTTP/HTTPS, and the HTTP derived (insecure) hkp and TLS-secured hkps protocols. The whole point of PGP is that you don't trust the source of the key without verification, so the protocol over which you receive the key doesn't matter. There exist a plethora of implementations that hide the trust-building exercise from users, and they're all for instant messaging. You can shoe horn that into email, but why? PGP is based on the web-of-trust principle of verification; if you just want the attestation that UserX probably owns KeyX, use a service that's tied to your phone number or email that doesn't use PGP -- i.e. textsure, telegram, whatsapp, etc.

by aroch 11y ago

nailer 11y ago

GPGTools is precisely the awful state of current of affairs I'm talking about. - GPGTools isn't sure what's called. GPGTools? OK where do I download GPGTools? There's no button to do that. What's GPGSuite? Do I want that instead? Installed, there's nothing called either Applications/GPGTools or Applications/GPG Suite. - Its app is called 'GPG keychain' or similar. Nobody outside crypto folk care know what a keychain or, not should knowledge of a keychain app be required to send someone a message encrypted with their public key - The apps main focus is key management, and it's really poor at that. There's no way to discover people's GPG keys AFAICT - It's a plugin for Apple Mail and a command line app. Most people using Macs don't use either of those. And it's not promoted as a Mac mail plugin, which means most people will be disappointed when they use it. - It seems to choke on common GPG output with some chars. That output is probably not encoded correctly, that shouldn't matter. Be liberal in what you accept.

aroch 11y ago
1) If installing something is enough of a hurdle that you can't complete it, then no amount of simplification beyond bundling is going to solve that 2) Everyone and their mother understand that keychains hold keys. You have to get to a key somehow, the onboarding process is a simple wizard. Again, if you can't follow prompts to enter an email, enter a password, and wiggle your mouse around; no amount of simplification is going to solve the problem. 3) You use the search for key button... 4) I'd argue that the vast majority of Mac users, especially the ones that are not technically inclined enough to use GPG on cli but want to, use the built in Mail.app. 5) gpg seems to have a slew of text encoding gotchas, I'm not sure how those can be fixed without a lot of core dev effort
- oceanofsolaris 11y ago
  I think that your points 2) and 3) are not perfectly reasonable if you really want to reach those who are not yet using encryption. If you look at how keychains are usually used nowadays, they are an implementation detail you could and probably should hide from non-technical users. As you say yourself, in order to find a key, you use the search for key button. Which prompts the program to look on a keyserver. You then import the first non-expired key you find for the desired email address. Why not do this automatically? You just annoy users who have to go through two (highly non-self-evident) steps and who do neither know nor care what a 'key' is. They just want to write secure email to their friends. (and btw, does the key-search even go over a secure connection with a pinned certificate? Because else you are not even trying to avoid MITM attacks). Is it too much to ask these users to read the manual, learn about which kind of key is the most secure yet also compatible with the GPG versions of their friends, find out how many bits theirs should have, have them wiggle their mouse (why, couldn't you use /dev/urandom for most cases?), upload their key to a keyserver, search their friends key from a keyserver, learn about the web of trust and go to a key-signing party? Is this too much to ask? Probably yes. I did not need to acquire a similar amount of knowledge about TextSecure and yet it probably transmits my messages in a more secure form than GPG. I am not saying that key-discovery is super-easy and all these are completely solved problems. But why do you have to make it so much more complicated for users than it has to be?
  - aroch 11y ago
    PGP is not supposed to be TOFU, friction to adding/trusting keys is part of the point of PGP -- verification of trust. If clicking a prominently placed button to lookup a key is not intuitive, then how do these users manage the just as unintuitive process of finding, verifying, and installing an application on their device? Keys are searchable over HTTP/HTTPS, and the HTTP derived (insecure) hkp and TLS-secured hkps protocols. The whole point of PGP is that you don't trust the source of the key without verification, so the protocol over which you receive the key doesn't matter. There exist a plethora of implementations that hide the trust-building exercise from users, and they're all for instant messaging. You can shoe horn that into email, but why? PGP is based on the web-of-trust principle of verification; if you just want the attestation that UserX probably owns KeyX, use a service that's tied to your phone number or email that doesn't use PGP -- i.e. textsure, telegram, whatsapp, etc.