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style: Reorganize and tweak email-related pages (#2973)

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Signed-off-by: Jonah Aragon <jonah@privacyguides.org>
Signed-off-by: Daniel Gray <dngray@privacyguides.org>
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12
docs/basics/account-creation.md
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@ -42,7 +42,7 @@ You will be responsible for managing your login credentials. For added security,
#### Email aliases
If you don't want to give your real email address to a service, you have the option to use an alias. We described them in more detail on our email services recommendation page. Essentially, alias services allow you to generate new email addresses that forward all emails to your main address. This can help prevent tracking across services and help you manage the marketing emails that sometimes come with the sign-up process. Those can be filtered automatically based on the alias they are sent to.
If you don't want to give your real email address to a service, you have the option to use an alias. We describe them in more detail on our email services recommendation page. Essentially, alias services allow you to generate new email addresses that forward all emails to your main address. This can help prevent tracking across services and help you manage the marketing emails that sometimes come with the sign-up process. Those can be filtered automatically based on the alias they are sent to.
Should a service get hacked, you might start receiving phishing or spam emails to the address you used to sign up. Using unique aliases for each service can assist in identifying exactly what service was hacked.
@ -50,19 +50,19 @@ Should a service get hacked, you might start receiving phishing or spam emails t
### "Sign in with..." (OAuth)
OAuth is an authentication protocol that allows you to register for a service without sharing much information with the service provider, if any, by using an existing account you have with another service instead. Whenever you see something along the lines of "Sign in with *provider name*" on a registration form, it's typically using OAuth.
[Open Authorization (OAuth)](https://en.wikipedia.org/wiki/OAuth) is an authentication protocol that allows you to register for a service without sharing much information with the service provider, if any, by using an existing account you have with another service instead. Whenever you see something along the lines of "Sign in with *provider name*" on a registration form, it's typically using OAuth.
When you sign in with OAuth, it will open a login page with the provider you choose, and your existing account and new account will be connected. Your password won't be shared, but some basic information typically will (you can review it during the login request). This process is needed every time you want to log in to the same account.
The main advantages are:
- **Security**: you don't have to trust the security practices of the service you're logging into when it comes to storing your login credentials, because they are stored with the external OAuth provider, which when it comes to services like Apple and Google typically follow the best security practices, continuously audit their authentication systems, and don't store credentials inappropriately (such as in plain text).
- **Ease of use**: multiple accounts are managed by a single login.
- **Security**: You don't have to trust the security practices of the service you're logging into when it comes to storing your login credentials because they are stored with the external OAuth provider. Common OAuth providers like Apple and Google typically follow the best security practices, continuously audit their authentication systems, and don't store credentials inappropriately (such as in plain text).
- **Ease-of-use**: Multiple accounts are managed by a single login.
But there are disadvantages:
- **Privacy**: the OAuth provider you log in with will know the services you use.
- **Centralization**: if the account you use for OAuth is compromised, or you aren't able to log in to it, all other accounts connected to it are affected.
- **Privacy**: The OAuth provider you log in with will know the services you use.
- **Centralization**: If the account you use for OAuth is compromised, or you aren't able to log in to it, all other accounts connected to it are affected.
OAuth can be especially useful in those situations where you could benefit from deeper integration between services. Our recommendation is to limit using OAuth to only where you need it, and always protect the main account with [MFA](multi-factor-authentication.md).

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docs/basics/email-security.md
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@ -5,17 +5,17 @@ icon: material/email
description: Email is insecure in many ways, and these are some of the reasons it isn't our top choice for secure communications.
---
Email is an insecure form of communication by default. You can improve your email security with tools such as OpenPGP, which add End-to-End Encryption to your messages, but OpenPGP still has a number of drawbacks compared to encryption in other messaging applications.
Email is an insecure form of communication by default. You can improve your email security with tools such as OpenPGP, which add end-to-end encryption to your messages, but OpenPGP still has a number of drawbacks compared to encryption in other messaging applications.
As a result, email is best used for receiving transactional emails (like notifications, verification emails, password resets, etc.) from the services you sign up for online, not for communicating with others.
## Email Encryption Overview
The standard way to add E2EE to emails between different email providers is by using OpenPGP. There are different implementations of the OpenPGP standard, the most common being [GnuPG](https://en.wikipedia.org/wiki/GNU_Privacy_Guard) and [OpenPGP.js](https://openpgpjs.org).
The standard way to add E2EE to emails between different email providers is by using OpenPGP. There are different implementations of the OpenPGP standard, the most common being [GnuPG](../encryption.md#gnu-privacy-guard) and [OpenPGP.js](https://openpgpjs.org).
Even if you use OpenPGP, it does not support [forward secrecy](https://en.wikipedia.org/wiki/Forward_secrecy), which means if either your or the recipient's private key is ever stolen, all previous messages encrypted with it will be exposed. This is why we recommend [instant messengers](../real-time-communication.md) which implement forward secrecy over email for person-to-person communications whenever possible.
Even if you use OpenPGP, it does not support [forward secrecy](https://en.wikipedia.org/wiki/Forward_secrecy), which means if the private key of either you or the message recipient is ever stolen, all previous messages encrypted with it will be exposed. This is why we recommend [instant messengers](../real-time-communication.md) which implement forward secrecy over email for person-to-person communications whenever possible.
There is another standard which is popular with business called [S/MIME](https://en.wikipedia.org/wiki/S/MIME), however, it requires a certificate issued from a [Certificate Authority](https://en.wikipedia.org/wiki/Certificate_authority) (not all of them issue S/MIME certificates, and often a yearly payment is required). In some cases it is more usable than PGP because it has support in popular/mainstream email applications like Apple Mail, [Google Workplace](https://support.google.com/a/topic/9061730), and [Outlook](https://support.office.com/article/encrypt-messages-by-using-s-mime-in-outlook-on-the-web-878c79fc-7088-4b39-966f-14512658f480). However, S/MIME does not solve the issue of lack of forward secrecy, and isn't particularly more secure than PGP.
There is another standard which is popular with business called [S/MIME](https://en.wikipedia.org/wiki/S/MIME), however it requires a certificate issued from a [Certificate Authority](https://en.wikipedia.org/wiki/Certificate_authority) (not all of them issue S/MIME certificates, and often a yearly payment is required). In some cases it is more usable than PGP because it has support in popular/mainstream email applications like Apple Mail, [Google Workplace](https://support.google.com/a/topic/9061730), and [Outlook](https://support.office.com/article/encrypt-messages-by-using-s-mime-in-outlook-on-the-web-878c79fc-7088-4b39-966f-14512658f480). However, S/MIME does not solve the issue of lack of forward secrecy, and isn't particularly more secure than PGP.
## What is the Web Key Directory standard?
@ -23,13 +23,13 @@ The [Web Key Directory (WKD)](https://wiki.gnupg.org/WKD) standard allows email
In addition to the [email clients we recommend](../email-clients.md) which support WKD, some webmail providers also support WKD. Whether *your own* key is published to WKD for others to use depends on your domain configuration. If you use an [email provider](../email.md#openpgp-compatible-services) which supports WKD, such as Proton Mail or Mailbox.org, they can publish your OpenPGP key on their domain for you.
If you use your own custom domain, you will need to configure WKD separately. If you control your domain name, you can set up WKD regardless of your email provider. One easy way to do this is to use the "[WKD as a Service](https://keys.openpgp.org/about/usage#wkd-as-a-service)" feature from keys.openpgp.org, by setting a CNAME record on the `openpgpkey` subdomain of your domain pointed to `wkd.keys.openpgp.org`, then uploading your key to [keys.openpgp.org](https://keys.openpgp.org). Alternatively, you can [self-host WKD on your own web server](https://wiki.gnupg.org/WKDHosting).
If you use your own custom domain, you will need to configure WKD separately. If you control your domain name, you can set up WKD regardless of your email provider. One easy way to do this is to use the "[WKD as a Service](https://keys.openpgp.org/about/usage#wkd-as-a-service)" feature from the `keys.openpgp.org` server: Set a CNAME record on the `openpgpkey` subdomain of your domain pointed to `wkd.keys.openpgp.org`, then upload your key to [keys.openpgp.org](https://keys.openpgp.org). Alternatively, you can [self-host WKD on your own web server](https://wiki.gnupg.org/WKDHosting).
If you use a shared domain from a provider which doesn't support WKD, like @gmail.com, you won't be able to share your OpenPGP key with others via this method.
If you use a shared domain from a provider which doesn't support WKD, like `@gmail.com`, you won't be able to share your OpenPGP key with others via this method.
### What Email Clients Support E2EE?
Email providers which allow you to use standard access protocols like IMAP and SMTP can be used with any of the [email clients we recommend](../email-clients.md). Depending on the authentication method, this may lead to the decrease security if either the provider or the email client does not support OATH or a bridge application as [multifactor authentication](multi-factor-authentication.md) is not possible with plain password authentication.
Email providers which allow you to use standard access protocols like IMAP and SMTP can be used with any of the [email clients we recommend](../email-clients.md). Depending on the authentication method, this may lead to decreased security if either the provider or the email client does not support [OAuth](account-creation.md#sign-in-with-oauth) or a bridge application as [multifactor authentication](multi-factor-authentication.md) is not possible with plain password authentication.
### How Do I Protect My Private Keys?
@ -39,14 +39,14 @@ It is advantageous for the decryption to occur on the smart card to avoid possib
## Email Metadata Overview
Email metadata is stored in the [message header](https://en.wikipedia.org/wiki/Email#Message_header) of the email message and includes some visible headers that you may have seen such as: `To`, `From`, `Cc`, `Date`, `Subject`. There are also a number of hidden headers included by many email clients and providers that can reveal information about your account.
Email metadata is stored in the [message header](https://en.wikipedia.org/wiki/Email#Message_header) of the email message and includes some visible headers that you may have seen such as `To`, `From`, `Cc`, `Date`, and `Subject`. There are also a number of hidden headers included by many email clients and providers that can reveal information about your account.
Client software may use email metadata to show who a message is from and what time it was received. Servers may use it to determine where an email message must be sent, among [other purposes](https://en.wikipedia.org/wiki/Email#Message_header) which are not always transparent.
### Who Can View Email Metadata?
Email metadata is protected from outside observers with [Opportunistic TLS](https://en.wikipedia.org/wiki/Opportunistic_TLS) protecting it from outside observers, but it is still able to be seen by your email client software (or webmail) and any servers relaying the message from you to any recipients including your email provider. Sometimes email servers will also use third-party services to protect against spam, which generally also have access to your messages.
Email metadata is protected from outside observers with [opportunistic TLS](https://en.wikipedia.org/wiki/Opportunistic_TLS), but it is still able to be seen by your email client software (or webmail) and any servers relaying the message from you to any recipients including your email provider. Sometimes email servers will also use third-party services to protect against spam, which generally also have access to your messages.
### Why Can't Metadata be E2EE?
Email metadata is crucial to the most basic functionality of email (where it came from, and where it has to go). E2EE was not built into the email protocols originally, instead requiring add-on software like OpenPGP. Because OpenPGP messages still have to work with traditional email providers, it cannot encrypt some of this email metadata required for identifying the parties communicating. That means that even when using OpenPGP, outside observers can see lots of information about your messages, such as whom you're emailing, when you're emailing, etc.
Email metadata is crucial to the most basic functionality of email (where it came from, and where it has to go). E2EE was not built into standard email protocols originally, instead requiring add-on software like OpenPGP. Because OpenPGP messages still have to work with traditional email providers, it cannot encrypt some of this email metadata required for identifying the parties communicating. That means that even when using OpenPGP, outside observers can see lots of information about your messages, such as whom you're emailing, when you're emailing, etc.