How To Send Secure Email Attachments – There is a growing awareness of the importance of keeping your information secure and many people are now looking for ways to protect their internet communications. With Google raising standards for secure HTTP connections and GDPR re-emphasizing the importance of protecting information in your custody and in transit, the spotlight is on insecure, ubiquitous email.

How To Send Secure Email Attachments

Electronic mail, which originated in the 1960s, was originally a means of leaving messages for users on time-sharing systems. As the US began connecting various institutions to the ARPANET, the use of electronic mail systems grew and became a way to send messages and files between users in different locations. Eventually, a standardized protocol for sending and receiving messages emerged from the large number of programs created for sending messages, and the Simple Mail Transport Protocol was born.

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The nature of SMTP meant that messages (emails) were sent as plain text. In the 1990s, with the rise of the World Wide Web, people became interested in SMTP security to protect their messages from eavesdropping. Several alternatives were investigated, but the use of SSL/TLS for secure communication (STARTTLS) was the most common.

This meant that email was still sent as plain text, but over an encrypted communication channel from the email client to the email server. Think of it as a hidden tunnel between your email and the server, your emails still go through the tunnel in plain text. This adds some protection against eavesdropping, but does not secure the email or its contents, and once that email is delivered to the first email server, it is accessible to anyone with access to the server, and there is no guarantee that the next hops and the final delivery are secured with TLS.

Encryption works fine in most cases. Well, there are different vulnerabilities in different encryption techniques and different attack vectors have been discovered that bypass encryption, but overall the encryption bit works. The problem is in the decoding.

If I encrypt a file or message and then send it to a recipient over a public or open network such as the Internet, I can be sure that even if other people intercept the message or file, they will not be able to read it without first being able to to decrypt it. But the exact same problem lies with the intended recipient of the email or file, they also need to know how to decrypt it before they can read it.

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So the first problem is to let the recipient know what technique I used to encrypt the file. Because there is no built-in encryption (with which files or e-mails can be sent) or one standardized form of encryption on our devices, both the sender and the recipient must agree in advance about the technique used.

The second problem is getting the key needed to decrypt the email or file sent to the recipient in a way they can understand but would have no meaning to anyone else who intercepted it.

Some of the encryption techniques listed here use public key encryption (known as PKE, PKC (Public Key Cryptography), or asynchronous encryption), where you freely share the public portion of your encryption certificate with anyone, but anyone to whom you send information , also need an encryption key.certificate. The others are password-based encryption (also known as synchronous encryption because the same password is used to encrypt and decrypt the item), where you need a copy of the password for the recipient separate from the encrypted files. (See note on passwords below)

If you want to encrypt the entire email, i.e. the contents of the email and attachments, you have several options.

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This is one of the MIME standards for secure data, developed in 1995, and as such your email client may already have a way to implement S/MIME encryption.

MIME (Multipurpose Internet Mail Extension) was developed to enhance the native ASCII text email. It made it possible to add audio, video, etc. to emails, have multi-part messages (such as plain text and HTML), and extend header information, which is hidden information that email systems used to provide additional features.

S/MIME uses certificates to authenticate the sender and receiver, different certificate classes provide different levels of owner authentication.

A root certificate, class 1, verifies that the ‘From’ field belongs to the sender/ It does not verify anything else about the sender. This means that the recipient knows that the email is not from a spoofed address or that the sender is trying to disguise their identity.

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A Class 2 certificate provides more thorough authentication. The identity of the person and/or organization is also confirmed before a Class 2 certificate is issued.

Certificates (or keys) are issued by a globally trusted provider and are stored on a network of publicly accessible CA servers. everyone, i.e. public part, and is used in combination with the private part of the key to encrypt and decrypt messages)

OpenPGP is a coding standard developed to enable the interoperability of software built to be OpenPGP compliant. It also uses public key encryption to encrypt/decrypt messages.

Many applications now use OpenPGP to encrypt much more than email, such as instant messaging, full disk encryption, file sharing, and web services.

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If we only look at email and file encryption apps, there are plenty of apps for Mac, Linux, Windows, iOS and Android that are compatible.

OpenPGP differs from S/MIME in the way certificates are made available. Instead of a trusted authority server with a public key directory, it uses PGP to determine the authority of a Web Of Trust (WOT) certificate. Because users trust certificates, this information is sent to other recipients with whom they communicate, spreading the trust level of the certificate from user to user.

Newer versions of OpenPGP include the ability to create certificate authorities similar to the S/MIME implementation, not only confirming that the key belongs to the owner, but also that the owner is trusted and lower trusted keys with its own keys can sign.

OpenPGP and S/MIME provide email signing, it is not a form of encryption and the email is still sent in plain text.

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A digital signature used when signing emails is a way of verifying the sender’s email address and verifying that the email has arrived without being altered along the way.

The email is signed with the sender’s private key. Upon receipt, the recipient downloads a copy of the sender’s public key (sent with the message, via WOT, or accessible from one of the CA directories) and can use it to verify the integrity of the email.

(not the sender) and the integrity of the email (not tampered with between sender and recipient) Does not guarantee that the sender or company is who they say they are. This means you can be sure that the sender had access to the email address the email came from (it was not spoofed), but not that the email address represents the sender. For example, a sender can create an email account [email protected] and their ownership of that address is confirmed by a signed certificate, there is no verification that it is actually Joe Bloggs who set up the address.

If you just want to encrypt the files you send and not the actual emails, file encryption is the way to go. Most tools still require both the sender and recipient to have the program installed and password or certificate sharing in place.

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As we mentioned earlier, the strength of the encryption ultimately depends on how strong the password is and how hard it is to guess when using a passkey to encrypt a file.

Strong passwords consist of a mix of upper and lower case letters, numbers and punctuation marks, combine words to make longer passwords and never use the same password twice!

An example of a good password is Micra/AB56DNW#[email protected], consisting of your car model in capital letters, your license plate in capital letters, the last part of your telephone number and your work zip code in small letters.

If you share files with your customers, you may want to agree on a system so that you don’t have to tell your customer the password every time. Perhaps a recommendation to use the customer’s reference number followed by a # and the date the email was sent in 8 digit format followed by / and then the zip code of the customer’s office could be lowercase to work.

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