Secure email works exactly the same as ordinary email. The difference is your email program automatically encrypts the transmission of a message so that nobody can read it from the time it leaves your email program until it gets to your email server. In other words, at any point in the path from your email program to your email server (i.e., your email service provider’s email server) that a hacker intercepts your message, the hacker will not be able to read the message because it’s transmitted securely. RMail Inbox is an example of a secure email system.
Next, your secure email server sends your message over the internet to the recipient’s email server. Most secure email systems will first try to send a message to the recipient’s server through a secure transmission. Whether this is possible, however, entirely depends on settings on the recipient’s email server over which you (the sender) have no control. In fact, you don’t even know. Once your message leaves your email server, you have no control over it unless you use RMail Message-Level encryption (read Chapter 9). See Fatal Flaws below for a further explanation.
Half Secure
When your email gets to your recipient’s email server it’s only normal email beyond that point and is not necessarily encrypted. What happens after that depends on your recipient’s email system. Since most people don’t have secure email system, it likely that the remainder of the email path is unsecure and subject to hacking.
Thus, you might say that by using a secure email system such as RMail Inbox, your email is half-secure or secure halfway (unless you use RMail Message-Level encryption).
However, it’s important to note that it’s your half of the email path that’s secure. That protects you sending and receiving emails as much as possible. You’ve done the best you can do to keep your email secure without using a special encryption service, such as RMail Message-Level encryption.
In Some Cases
But that’s not the last word. If the recipient has a secure email service as well as you, your email message may trigger secure transmission between the two email servers. Your message will, therefore, go automatically encrypted along the entire email path from your email program to the recipient’s email program. But read Fatal Flaws below.
Gmail
Gmail is a secure email system. If you use RMail Inbox and the recipient uses Gmail, your email message will theoretically go over the entire email path encrypted.
In Other Cases
Another scenario is that the recipient has the same secure email service provider as you do. That means that your message never leaves the provider’s email server. It goes from your email program to your email server (i.e., your email service provider’s email server, which happens to be the recipient’s email server too) to the recipient’s email program encrypted all the way. But see Fatal Flaws below.
Secure email services, although available, are not widely used. They are typically special services that cost a premium over normal email service. And many normal email services are free, such as Hotmail (Outlook.com Mail), giving folks an incentive not to use an email service that they have to pay for.
The current exception is Gmail, which turned into a secure email system recently. Note, however, that Google data mines the email that passes through the Gmail email server, which is a type of security breach itself (read Chapter 17).
The internet is migrating toward greater security, and more major services can be expected to be convert into secure email systems.
Fatal Flaws
There are several problems with the secure transmission SSL/TLS secure email scheme.
- When a message arrives at the email server from the sender through a secure transmission, it is not encrypted after arrival. At that point, those who administer the email server (the staff of the email service provider) can see the unencrypted messages of customers. And if a hacker gains access to the email server, the hacker can also see or even capture the unencrypted messages of the customers.
- When the sender’s email server sends a message to the recipient’s email server, the two email servers negotiate how the message will be sent. If both of the servers are secure (using TLS), the sender’s email server will send the message through a secure transmission (using TLS). If the recipient’s email server is not secure, the sender’s email server will send the message unencrypted. But, in fact, not all secure email servers are configured to receive an encrypted message, even though they have the capability. And not all secure email servers use TLS. And some email servers may not be working properly. These facts create a lot of unknowns leaving reliance on TLS alone unreliable, as a practical
- When a message goes from the sender’s email server to the recipient’s email server over the internet, it is particularly vulnerable to interception. If unencrypted, there is no security. But in some cases, the message is vulnerable because the sender’s email server can be tricked into concluding that the recipient’s email server is not able to receive the transmission even though it can. In the case of an interception, the interceptor’s (hacker’s) software can negotiate with the sender’s email server to send the message unencrypted rather than through a secure TLS transmission. This is called a TLS downgrade attack. A hacker can simply downgrade the security of the message transmitted over the internet (from encrypted to unencrypted) and then intercept it and read it.
- People using TLS secure email seldom, if ever, know exactly what will happen on the path of a message between sender and recipient. In other words, they never know for sure whether the message is really secure.
Consequently, the security of a secure email system based on TLS is not hackproof. Even though it’s not hackproof, however, it’s better than no security; that is, it reduces substantially the risk of being hacked.
Note that the RMail email encryption services return a useful Registered Receipt email record that may serve as proof of the fact of encrypted delivery. This is particularly useful if a sender is later accused of transmitting some sensitive information in the clear even though they actually encrypted it.
Office Email System
Email has enjoyed universal use, primarily because everyone has easy and inexpensive access to it. A small office (or even your home) can as easily afford an email system as a large enterprise can. And while we think of email as a means of communications between ourselves and the outside world, the truth is that email has also become a platform for the inner-office memo.
In other words, people within an office, whether small or large, communicate with each other via email simply because it’s a convenient and inexpensive inner-office memo system. Consequently, it’s not unusual for you to send an email to the person in the office next to you, even a message with digital documents attached. The result is that email messages become a record of how you have interacted with other people in your organization, as well as how you have interacted with outside clients, customers, vendors, organizations, etc.
So keeping Chapter 2 in mind, let’s trace how an email message goes from your email program to the email program of the person in the office next door to you. First, it goes to your wireless router. Then it goes across the internet to your email provider’s email server. Then, it comes back across the internet to your wireless router. From your wireless router, it goes to the recipient’s computer and email program, even in the office next door. This being so, when you send an email to your coworker, it’s transmitted locally twice and goes across the internet twice. (If you don’t have a wireless router but instead have a router that works with network cables, it’s not transmitted locally twice, but it still goes across the internet twice.)
As you can see this is a lot of vulnerability for an in-office memo system. See Chapter 4. One way to defend against this vulnerability, of course, is to set up your router properly as outlined in Chapter 19. Another way is to simply use network cables instead of Wi-Fi. But whatever you do about local transmissions, that still leaves two transmissions across the internet that are vulnerable.
Now, suppose you use a secure email system with RMail Inbox being the prime example. That means everyone in your office uses RMail. By using RMail Inbox your email messages are automatically encrypted from your email program to the RMail email server, and they don’t leave the RMail server except to return encrypted to your office. Thus, an inner-office email (memo) still goes across the internet twice, but it goes across encrypted. Anyone intercepting it cannot read it.
It’s easy to see that with a secure email system, such as RMail Inbox, your inner-office email is secure, at least from external hackers. This makes a powerful case for those interested in inner-office email security to convert to RMail Inbox, RMail Web, or a comparable secure email service.
Note that enterprise email systems provide security, and the inner-office email is protected.
Case Study
In 2006 I had a valuable domain name hijacked. It was stolen because somebody was able to first hijack my email identity and then hack into my account for the domain name. I didn’t even find out about it until a week after it happened. The official new owner was someone in Algeria!
At that point, it took me almost three weeks working five or six hours a day every day to get my domain name back. My domain name registrar was very diligent in helping me, but I also had to hire a lawyer to write letters to various organizations, which cost me several thousand dollars. That’s when I first learned about secure email.
After that, I used LuxSci as my secure email service provider and did not had any trouble. When I sent and received email via LuxSci, my email messages were automatically encrypted between my email program and the LuxSci email server. LuxSci charged a monthly fee, but the fee was well worth the security it provided. (RMail Inbox provides the same secure email service free, and I use RMail Inbox with the email address of Sinclair@RMail.com.)
Recurring Theme
How do you make your messages more secure than the automatic secure transmissions enabled by secure email systems? In other words, how do you make your email more secure than RMail Inbox or RMail Web used alone? You can opt to use these together with RMail Message-Level encryption, at a low cost, which encrypts email all the way from your email program to the recipient’s email program.
The Last Word
This ebook is not the last word on email security, nor is RMail alone the last word on email security. Email security is a very complex technology. This book is not about completely eliminating security risks from email. The email system is not designed to do so, and only special software and inconvenient encryption practices can reduce the risks to almost zero. Rather this book is about instituting secure practices that will reduce the risks significantly so that your chances of becoming the victim of a hacker will be remote, not inevitable. And that’s certainly worth the effort.
