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I don't get it. What's hard about GPG or S/MIME-encrypted mail? You set up the thing to integrate with the MUA once (in GPG's case, S/MIME are supported out-of

I don't get it. What's hard about GPG or S/MIME-encrypted mail? You set up the thing to integrate with the MUA once (in GPG's case, S/MIME are supported out-of-the-box with most common desktop MUAs), then the only hassle is to enter password on startup or when reading the first message. And lock the computer properly when you're getting away. Write a message, tick "encrypt" (or don't untick it), send, done. Receive a message, see a badge "encrypted, verified", type a password (if key's not cached before), read it as usual, done. I fail to see how anything can be easier and less obstructive than this. At least, my only problem with encrypting email is that practically no one of my peers have keys published. This could be easily solved if mail client software vendors could make their products ask user to generate and backup a keypair on install. Oh, right, encryption has problems with webmail. Extension/userscript kludges are insecure (unless they open separate window/tab for anything private) and break with every other update.

dredmorbius 13y ago
I don't get it. I'm with you. I've had mutt set up to use PGP for ages. I've configured a half-dozen or more other MUAs to use PGP/GPG. If I've got an MUA that doesn't support PGP, I can do ASCII armor encryption and decryption easily. That's you and me, the geek set. The Google guy I mentioned: he's just as versed. And yet, felt he should give me grief. If you've got a Linux desktop, odds are that the tools you need are integrated. Congratulations, that's ... about 0.5-3% of all desktops depending on whose numbers you trust and/or like. And an increasing number of users are now on smartphones and tablets. Yes, I've got K9Mail, but I've received no, and sent very few, encrypted emails. In corporate environments, you get the tools you've got on a standard desktop and that's it. I've had a hell of a time convincing engineering and dev teams to create and use PGP/GPG keys and/or use SSH key authentication rather than passwords. I've been at shops recently which still use rsh (and had the pleasure of giving the solution to a user creating large numbers of client sessions: oh, yeah, SSH doesn't have the 512 max outbound connections limit that RSH does due to its privileged port use). Sigh. Key distribution is a huge part of the problem. In large part it's what PGP Corp (now part of Symantec) addressed with its appliance solutions: a box that creates, signs, manages, and automatically applies keys for users. I don't exist, and yet I've got a key published (and embedded in my G+ profile coverphoto). Oh, what the heck, let's add it to my HN profile. As you note: webmail, mobile, smartphone, and Windows are all problematic. But more than that: people don't fundamentally understand the technology they use (part of a much larger rant and topic), and this stuff confuses them utterly.
jmccree 13y ago
I'm not sure if you mean what's so hard for a "linux evangelist" or in general. Linux probably has the best and easiest GPG integration. In general, encrypted mail is practically useless for every day communication and provides little real benefit. Unless you only communicate with linux experts, 90%+ of the people you're talking to likely don't even know what a "MUA" is. I use gpg for transferring sensitive data (passwords, api keys) occasionally to the rare few clients that have gpg, but the rest of our emails are still sent unencrypted. Why? Encryption requires everyone in the thread to support it. Need to CC in the C-Level exec on something? Good luck getting them to setup it up in their outlook and use it properly. Even with my help, it took a good 30 mins to set my dad up with GPG on Windows/thunderbird. Have to figure out which software you need, the nomenclature for key generation etc is different in each program. Encryption breaks search, at least in thunderbird. You can't search through the encrypted messages and they aren't indexed. This makes sense if you're sending very sensitive data perhaps, but for general business correspondence it's reduces productivity. There's an open bug in EnigMail by a user who saves every email in plain text to use regular file search tools. That's useless. There's the aforementioned webmail. Tons of people only use webmail, and there's no way to interact with them. More importantly in my book, encryption breaks mobile access. Sure, there are addons for gpg on android, but I don't trust my private key on my phone. In the near future there may be some way to use a yubikey with NFC for passing in the private key, but that brings in it's own set of problems. Lastly, it's the cost/benefit that really keeps encryption use from being wide spread. It costs you time in getting each contact you use to use it, time dealing with being unable to search, time setting up your phone to securely access mail, unable to use webmail at all, and for all this you really only get two benefits: Prevention of e-mail interception by intelligence agencies or internet backbones and access to your mail by your e-mail provider. If I'm not concerned about these, just using proper TLS access for IMAP/SMTP prevents anyone I'm actually worried about (wifi interceptor, bad ISPs) from reading the mail. For mail inside an organization with their own mail server, mails are never anywhere unencrypted than company owned equipment, TLS in transit. Doing encryption right is hard, for 99% of email the threat model just doesn't justify the expense in time and headaches so the NSA doesn't know there's a conference call at 11am tomorrow or that you should call grandma tomorrow because it's her birthday.

dredmorbius 13y ago

I don't get it. I'm with you. I've had mutt set up to use PGP for ages. I've configured a half-dozen or more other MUAs to use PGP/GPG. If I've got an MUA that doesn't support PGP, I can do ASCII armor encryption and decryption easily. That's you and me, the geek set. The Google guy I mentioned: he's just as versed. And yet, felt he should give me grief. If you've got a Linux desktop, odds are that the tools you need are integrated. Congratulations, that's ... about 0.5-3% of all desktops depending on whose numbers you trust and/or like. And an increasing number of users are now on smartphones and tablets. Yes, I've got K9Mail, but I've received no, and sent very few, encrypted emails. In corporate environments, you get the tools you've got on a standard desktop and that's it. I've had a hell of a time convincing engineering and dev teams to create and use PGP/GPG keys and/or use SSH key authentication rather than passwords. I've been at shops recently which still use rsh (and had the pleasure of giving the solution to a user creating large numbers of client sessions: oh, yeah, SSH doesn't have the 512 max outbound connections limit that RSH does due to its privileged port use). Sigh. Key distribution is a huge part of the problem. In large part it's what PGP Corp (now part of Symantec) addressed with its appliance solutions: a box that creates, signs, manages, and automatically applies keys for users. I don't exist, and yet I've got a key published (and embedded in my G+ profile coverphoto). Oh, what the heck, let's add it to my HN profile. As you note: webmail, mobile, smartphone, and Windows are all problematic. But more than that: people don't fundamentally understand the technology they use (part of a much larger rant and topic), and this stuff confuses them utterly.

jmccree 13y ago

I'm not sure if you mean what's so hard for a "linux evangelist" or in general. Linux probably has the best and easiest GPG integration. In general, encrypted mail is practically useless for every day communication and provides little real benefit. Unless you only communicate with linux experts, 90%+ of the people you're talking to likely don't even know what a "MUA" is. I use gpg for transferring sensitive data (passwords, api keys) occasionally to the rare few clients that have gpg, but the rest of our emails are still sent unencrypted. Why? Encryption requires everyone in the thread to support it. Need to CC in the C-Level exec on something? Good luck getting them to setup it up in their outlook and use it properly. Even with my help, it took a good 30 mins to set my dad up with GPG on Windows/thunderbird. Have to figure out which software you need, the nomenclature for key generation etc is different in each program. Encryption breaks search, at least in thunderbird. You can't search through the encrypted messages and they aren't indexed. This makes sense if you're sending very sensitive data perhaps, but for general business correspondence it's reduces productivity. There's an open bug in EnigMail by a user who saves every email in plain text to use regular file search tools. That's useless. There's the aforementioned webmail. Tons of people only use webmail, and there's no way to interact with them. More importantly in my book, encryption breaks mobile access. Sure, there are addons for gpg on android, but I don't trust my private key on my phone. In the near future there may be some way to use a yubikey with NFC for passing in the private key, but that brings in it's own set of problems. Lastly, it's the cost/benefit that really keeps encryption use from being wide spread. It costs you time in getting each contact you use to use it, time dealing with being unable to search, time setting up your phone to securely access mail, unable to use webmail at all, and for all this you really only get two benefits: Prevention of e-mail interception by intelligence agencies or internet backbones and access to your mail by your e-mail provider. If I'm not concerned about these, just using proper TLS access for IMAP/SMTP prevents anyone I'm actually worried about (wifi interceptor, bad ISPs) from reading the mail. For mail inside an organization with their own mail server, mails are never anywhere unencrypted than company owned equipment, TLS in transit. Doing encryption right is hard, for 99% of email the threat model just doesn't justify the expense in time and headaches so the NSA doesn't know there's a conference call at 11am tomorrow or that you should call grandma tomorrow because it's her birthday.