Poll: Do you encrypt your email?

> I'd like to, but the people I email don't know how to (or won't) use encryption.

The situation today is even less conducive to getting the people I email to use encryption than it was 10 years ago. In the past there was maybe a chance I could convince people to install a plugin, or in the case of family members I could set it up myself when visiting. But now everyone uses Gmail, and often uses it from multiple devices, which makes that difficult. There are browser plugins that will try to do GPG in Javascript, but they seem to break routinely with Gmail changes, and the one that used to be most used (FireGPG) was discontinued. And the Gmail app on mobile devices doesn't support such extensions anyway.

I don't if its borne more out of cynicism or laziness, but I feel as though if a shadowy government organization has the ability to peer into every major facet of the Internet, me encrypting my email isn't going to do much to stop them from getting whatever they want to know about me.

(Put another way: I'm more embarrassed about the subreddits I browse than the emails I send.)

One thing being left out of this discussion so far is signing, which is arguably just as important in many cases as encryption. There are a fair number of situations where you don't care all that much who can see the data, but you care a lot that it comes from the person you think it does. I think it's worth mentioning, since encryption and signing generally go hand in hand.

a couple of years ago i started signing my emails.

unfortunately a lot of my mails got deleted by the recipients, because there were "some very strange things" (the signature) at the end of my mails and they were afraid of malware like viruses or trojans.

i wanted to increase the level of trust in my messages and achieved the complete opposite.

i stopped signing my mails a couple of weeks later, after a clients secretary phoned me to inform me "i had a virus on my computer".

Using GPG, I encrypt sensitive e-mail, such as e-mails that include credentials for another system. However, I do not encrypt all e-mail, even to recipients who use GPG.

The bottom line is this: the user interface of GPG is awful--among the worst this side of Git. "Barely usable" is the briefest way I can describe it.

And it's not the key exchange that makes it so bad; exchanging keys is the easy part. My gripe is with the routine UI clunkiness of GPG. For example, it's not possible to paste into or use Keepass' "auto-type" feature to type my passphrase into the GPG dialog. So I have to manually type my sequence of 50 random letters, numbers, and symbols nearly every time I receive an encrypted e-mail. It's so bad that unless an encrypted e-mail is urgent, I'll defer it until I'm in the mood to look up and type my passphrase.

> None of the above.

I'd use encryption and try to convince others to as well, but I rely on email search too much. I'm sure a lot of people don't bother to 'tag' or 'label' their email, but instead rely on search to find messages with certain content in them. Maybe I'm wrong, but I don't see a way to have both with the server being unable to read the contents of the email to build a search index.

I just tried GPGTools[1]; I generated a key and set it as default in Preferences. I sent a test email with the "OpenPGP" button glowing. I'm prompted for the password, yet it's still sent as plaintext - it only adds a signature to the bottom of the email. Why doesn't it encrypt the text? Does it have to be email?

I also can't use S/MIME even though I got a certificate, I don't know how to use it.

[1] https://gpgtools.org/

Encrypting the message content sounds sensible. But as far as I'm aware you can't encrypt the to/from fields.

As we've seen recently, this kind of metadata is often just as revealing as the content.

Encryption for email is probably giving you a false sense of security. If you care about privacy, email feels inappropriate to me.

So then the question is, what is the alternative? Honest question—I feel kind of helpless about it.

I actually had a few of my friends using OTR, until they realized that

- it's extremely buggy between software (e.g. Jitsi + Gibberbot)

- it's a huge hassle to use on multiple devices

Then PRISM came out and... they didn't care.

Email is the same way: give me a way to, without spending much extra time, use encrypted email on my phone and any computer I come across, and I'll use it. Otherwise, it doesn't seem worth it.

The best thing I can come up with is js based encryption, where the server stores my private key, encrypted. For widespread adoption, though, you'd still need an Android app, an iPhone app, and a Windows 8 app, and it goes without saying that browser-based encryption in js is subject to a myriad of attacks.

What about, "I don't, because who cares?", or "I don't care."?

This poll is silly because "encrypting email" doesn't work like that. It requires (at least using PGP/GPG) both parties to participate!

So, I encrypt my email whenever I'm sending to someone with a key. I sign important emails.

So to find out how hard this was I recently tried to setup smime, and it actually isn't really that hard. No plugins required and fully integrated with Mall.app on mac, and my iOS devices. For easy steps on how to do this see here:

http://arstechnica.com/apple/2011/10/secure-your-e-mail-unde...

You can get a free cert from COMODO:

http://www.comodo.com/home/email-security/free-email-certifi...

What make s/mime easy to use is that those who receive the smime attachment on compatible software can see and validate signatures even without setting up their own s/mime identity. They can also accept your public key so when they do setup s/mime they are ready to encrypt message to you just using the signature attachment on one of your messages.

So s/mime at least has an intermediate value even if you are the only one of your friends using it. You can sign things and they can confirm your signature.

Also gpgtools (https://gpgtools.org) just released a new version that has a plugin for the latest Mail.app. However, public key infrastructure is a little more complicated process, and you'll have to explicitly acquire each person's key, and a signatures can not be validated until the recipient also has gpgtools installed.

As an ex cypherpunk, s/mime seems to have a number of security issues with it. First is how it is generated. When I got my cert from COMODO as outlined above the file was saved from the web browser to my downloads file. This struck me as odd. Does this mean they could have copy of my cert? This is convenient, but keys should be generated securely by the user on their own machine.

Also there is the issue of security in terms of how does the signature work. Does it sign then encrypt, or encrypt then sign, or sign then encrypt then sign again? See the non accepted answer by Adam Liss for a discussion of the security issues of this here:

http://stackoverflow.com/questions/13512026/how-to-check-if-...

Nevertheless s/mime works well in many tools and on iOS devices, and is not nearly as hard as most people think. Someone who wants to sell certs could make a video that even grandma could follow.

If my connection to my SMTP server is encrypted and my receiver's POP connection is encrypted, is there really a need to encrypt the message itself?

This is a bad poll. I use TLS for all my imap and internal smtp, and prefer using tls for anyone externally, but don't enforce tls or do cert checking for external mail.

I use PGP infrequently, but for sensitive things; for anything routine and sensitive (passwords), OTR over XMPP chat is easier to set up with most people.

I guess in this poll that's "regularly encrypt most but not all of my email"?

I only rarely encrypt email messages themselves, mostly because few (if any) of their recipients have personal certificates. Of my encrypted messages, most aren't sent using S/MIME or whatever we are calling the standard these days - recipients get a link to a web site, where they have to register an account, authenticate, and view the message. That's not only cheating; it's also pretty weak in terms of assuring confidentiality. To be honest I think the point of the web site is that it lets you send large files to people, not strong crypto.

All of the email servers I operate support STARTTLS. Transport-layer security is just as important to me as message integrity/confidentiality/authenticity. If I could get away with it, I would force all SMTP traffic over TLS, just like I already do with my web sites (even my intranet sites are HTTPS-only). As with my human correspondents, many of the MTAs out there don't support SMTP encryption.

At one point, I was able to get an S/MIME setup going in Mail.app, and it would automatically encrypt emails sent to others whom had previously sent me a signed message.

Unfortunately, there were tons of mailing lists and clients that would choke even on the signed messages, plus renewing the certificate and all that was too time consuming.

I'd like to, but it's too much trouble and noone else doesn't so it's pointless..

To echo some of the comments here, I think the main factors making this (PGP, GPG usage) unfeasible at the moment is:

1) Too hard for casual users (=others don't use it)

2) PGP/GPG is ridiculously difficult when using webmail or mobile email clients.

3) Your email usabiliy suffers. With this I'm referring to your ability to search your emails. Once you are using encryption, you can't find anything in it, unless the email is decrypted and saved plain in your email storage.

The usability part is actually forgotten quite a few times in discussion, but I think it's a big problem. If you opt to decrypt and save it, this would be ok, if it happens on your client (local db), but not stored remotely (eg. webmail/imap box). This problem comes with a whole lot of issues attached.

The results of this thread are disheartening. That said, the majority of technical people in my professional and social circles do not use any form of email encryption.

I think it comes down to a combination of how few people use it and how much more work is required. The only people I know who use it are exactly the ones you'd expect: those who do things like go to DEFCON every year.

That's not to say that my other friends aren't sometimes cautious with some of their data, they just go to the length of doing face-to-face sharing of physical media and not having intensely private/personal conversations over the phone. Basically they (we?) all just assume that there's no way to protect it once it's on the wire, so "why bother?".

I can't stress enough how important holding/going-to a CryptoParty (or similar) is.

At work, we use mail-system based encryption like Zix, IronPort or Voltage. Those solutions provide guaranteed encrypted transit to the recipients public network boundary. Depending on the content, the system either just ensures that messages travel via TLS or requires explicit authentication via a web interface.

In my personal life, I haven't used mail encryption since my college days with some crypto geek friends. I do have an OpenGPG card and public key published, but I mostly use it to encrypt data at rest on cloud storage platforms or USB keys.

Even if nobody you email uses PGP themselves, you can still get a lot of benefit from encrypting your email: https://grepular.com/Automatically_Encrypting_all_Incoming_E...

Even if you think that your email is unimportant and you've got nothing to hide, you probably still don't want people being able to use your email account to take over your other accounts (password reminders) if they get access to it.

Found this for gmail. no idea if it is good https://github.com/StreakYC/StreakSecureGmail

You have fragmented "I'd like to..." in 4 parts, I don't in 2, partial in 4 and "I do" in one. Be careful to interpret the results.

The only way to fix email is to make encryption mandatory.

I honestly encrypt email far more often in my government job than I do outside of work. Everything at my job is streamlined to support it, outside I'd have to convince people to install S/MIME or PGP for any one of numerous email clients. And mailing lists would be a whole 'nother separate ball of wax.

I don't think I've encrypted an actual email even once.

However, I do encrypt attachments or drop-box blobs from time to time. E.g., I might make a self-extracting PGP archive of a directory of tax info encrypted with a symmetric key, put it on Google Drive, and send the link to my accountant, having shared the key out of band.

Even if I did, nobody else does. So I just use https://www.noteshred.com to send encrypted messages to people that only needs a password to access.

I'd like to mention that a good part of my (professional) social network switches to retroshare. And I'm forced to go with them if I want to stay in touch. :)

All email is 'in the cloud' now...So Enigmail is too much of a hassle for my recipients.

At least Thunderbird and Evolution are being steadily developed now![I jest!]

I can but I don't need to. The receivers can't decrypt them.

Are you asking about email in transit or in storage?

Instead of encrypting I use lavabit.com

I would if i need to.

Unfortunately, it's a fool's errand.