Frequently Asked Questions

Why would I want to encrypt my email?

You would know better than I would. Maybe you don’t believe that you owe the NSA and other government bodies the automatic authority to access your communications without first obtaining a warrant. I’m vaguely aware of some legal precedent for that notion.

Alternatively, maybe you’d like to be able to email like-minded individuals about your My Little Pony obsession without Google serving you advertisements based on that interest.

If I don’t want people reading my email, why would I send it to enMailing for encryption/decryption?

Fortunately, that isn’t how enMailing works. I don’t want to read your emails any more than you want me reading them (I don’t have the time, and they’re probably boring anyway). The content of your messages is never sent to enMailing. When you encrypt a message, the only information that gets sent to enMailing is your enMailing username, password, and the group for which you want to encrypt the message. enMailing then responds with the proper encryption key and your message is encrypted locally on your computer or mobile device.

The decryption process is similar. enMailing affixes a header to the beginning of each encrypted message. This header contains the information necessary to determine which encryption key was used to encrypt the message. When you or a recipient tries to decrypt the message, only the header is sent to enMailing. enMailing then analyzes the header to determine if the person requesting decryption has access to that group. If the user has access, the server replies with the proper encryption key and the message is decrypted locally on the user’s computer or device. Again, the content of the message itself is never transmitted to enMailing, even in its encrypted form.

What are groups?

All of your contacts are automatically added to an “Everyone” group. When you send a message encrypted for this group, anyone you are currently connected to on enMailing will be able to decrypt it.

If you’re a premium user, you can create additional groups which hold subsets of your contacts. When you encrypt messages for these groups, only those group members will be able to decrypt the messages. Once you add someone to a group, they are able to decrypt all of the previous messages you have encrypted for that group. If that isn’t what you want, then you should probably just create a new group.

What if my encryption keys are compromised somehow?

enMailing is organized so the encryption keys are never directly exposed to the user. You shouldn’t ever see them, and neither should the people to whom you send messages. However, it’s possible that one of your contacts might take active efforts to capture your key when they decrypt a message you send to them. In that event, here are some recommendations: (1) get better friends, (2) remove that user from your contacts and/or assign them to their own group, and (3) renew your group keys.

Free users can renew the keys once every seven days. Premium users’ keys are automatically renewed once a week and premium users can manually update each group’s key once per day. Renewing a key simply changes the key used to encrypt/decrypt a message for that group. Any new messages you send for that group will be encrypted with the new key. You will still be able to decrypt messages sent with the old key. If you don’t want that, then just delete that group (note that you can’t delete your “Everyone” group).

Who can read my encrypted messages?

In order for someone to read your encrypted messages: (1) they have to have an enMailing account, (2) you have to be connected to them on enMailing, and (3) they have to be in the group for which you encrypted the message. Each enMailing membership comes with a free guest key. You can hand that key out to one of your friends and they’ll be able to set up an enMailing account for free. Their guest account will work for as long as your account stays active.

To connect to someone on enMailing, you just enter their username into the website and enMailing will send a connect request to that person. To respect each user’s privacy, there is no user search function. You have to know their exact username when you make the request. Note that when someone redeems your guest key, enMailing will automatically send a connect request for you.

Regarding groups, see a couple questions up.

What type of encryption does enMailing use?

enMailing utilizes AES encryption using the CBC mode of operation with a key size of 256 bits.

Is that type of encryption good enough?

That’s for you to decide. Since you can change your encryption keys once every week, it makes the prospect of a brute force attack considerably less attractive.

Why would I use enMailing versus any of the other email encryption services available?

One advantage of enMailing is that, as discussed above, the content of your messages never touches our server. This has obvious privacy advantages.

Another advantage is that it’s free. If you want to support enMailing, you can sign up for a premium account for $12 per year.

Finally, it’s easy. Other options for setting up encrypted email can be a huge pain. With enMailing, you don’t have to worry about manually distributing keys to all your friends; enMailing does that for you.

How do I use enMailing?

First, you sign up for an account. Next, you download and install one or more enMailing plugs (currently, enMailing supports Firefox, Chrome, Internet Explorer, Thunderbird, Outlook, iOS, and Android). From there, use diverges a bit depending on your application of choice.

For example, say you want to encrypt a message in Gmail using Firefox, Chrome, or Internet Explorer. All you have to do is type your message, and the hold ALT and click on the message body. enMailing will then encrypt your message. If you only want to encrypt a portion of the message, just highlight the portion you want to encrypt, right-click it and select “Encrypt Selection” from the enMailing menu. You can also change the group for which you are encrypting via the right-click menu. If you want to decrypt a message in Firefox or Chrome, just click on it.

In Thunderbird, enMailing handles decryption automatically when you view a message. To encrypt a message, use the added buttons on the toolbar or the right-click menu.

In Outlook, enMailing adds a decrypted message view to the bottom of the reading pane and the individual message window when you open a message. The options to encrypt a message are on the “Add-Ins” section of the ribbon interface when you’re composing a message. The plugin should work for Outlook 2007 and newer.

The enMailing iOS and Android apps allow you to encrypt and decrypt messages by copying and pasting them into the app. You can also manage your enMailing contacts and groups from the apps.

If you want more in-depth information, visit the guides section.

Will enMailing be available for any more platforms/applications?

I hope so. A Windows 10/Windows Phone app would probably be the next step, but I haven’t begun work on it yet. I’ll probably also write an extension for Microsoft Edge once it gets extension support.

Who is behind enMailing?

Right now, it’s just me, Dan N. I got an associate’s degree in computer programming some years ago. Since then I’ve dabbled in programming and websites.