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Encrypt Files Before Emailing: 5 Easy Methods [Windows]

November 10, 2011
Encrypt Files Before Emailing: 5 Easy Methods [Windows]

Protecting Email Communications: A Simpler Approach to Encryption

A recent experience highlighted the need for secure communication. I had a writer based in China, and we both suspected our email exchanges were under surveillance.

Initially, we implemented a comprehensive encrypted email system, VaultletSuite. This required installing dedicated client software on both our computers.

While VaultletSuite offered a high level of security, its complexity proved somewhat inconvenient. Logging into a separate email client solely for one contact was a cumbersome process.

An Alternative Encryption Method

For situations where you anticipate potential monitoring of your communications, a more streamlined solution exists: file encryption.

Encrypting files before emailing them provides a simpler and more accessible method of safeguarding sensitive information.

The recipient, possessing the correct password, can then decrypt and access the contents of the encrypted files. This avoids the need for specialized email clients.

This approach offers a balance between security and usability, making it a practical option for protecting your digital correspondence.

5 Methods for Securing Files Prior to Email Transmission

The practice of file encryption is well-established. As early as 2008, this topic received coverage, and we’ve since explored various applications designed to encrypt folders and drives, such as Mark’s assessment of TrueCrypt and my evaluation of AxCrypt.

The history of cryptography dates back to ancient Greece, where Spartans employed ciphers for confidential communication. Modern cryptography encompasses a vast range of algorithms that software can utilize to encrypt password-protected files, rendering them exceptionally difficult to decode. However, it’s important to acknowledge that absolute security is rarely guaranteed.

Employ Encrypt Files for Rapid File Protection

Each of the solutions presented here requires installation on both your computer and the recipient’s. Your software will encrypt files or messages using a password you provide, and the recipient’s software will decrypt the information.

Encrypt Files stands out as a particularly straightforward application for achieving this goal.

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Simply select the files you wish to protect, then click "Encrypt" in the left-hand panel. You will then be prompted to enter the desired password for encryption.

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A new, encrypted copy of the file will be created. The software allows you to choose from 13 different cryptographic algorithms and offers options to retain, delete, or securely shred the original files.

dsCrypt: Drag, Drop, and Encrypt

For exceptionally quick file encryption, dsCrypt, a small freeware application, is an excellent choice. Upon launching the executable, a small window appears on your screen.

Files can be easily dragged into the gray box, prompting the program to request a password.

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The files are then transformed into encrypted .dsc files. The recipient simply drops these files into the gray box, enters the correct password, and the files are decrypted and become usable. While the encryption may not be the most robust, it’s suitable for basic security needs.

MEO Encryption: Encrypt Files and Emails

MEO Encryption is another file encryption application that is highly recommended. This free software not only encrypts and decrypts files but also enables the sending of encrypted email messages.

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File encryption features include the option to save files as self-extracting executables.

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This eliminates the need for the recipient to install any software; they only require the correct password. Furthermore, the software can be configured to use any SMTP account, allowing it to directly encrypt and send email messages for you.

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Two cryptographic algorithms are available: a lighter one for faster encryption and a stronger one for slower, more secure encryption. Select the algorithm based on your specific requirements.

LockNote: Secure Simple Text Messages

To send text messages with enhanced privacy, consider using LockNote to write your message in a text file and save it in an encrypted format.

The application’s interface closely resembles Windows Notepad, but it prompts for a password when saving the file.

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The recipient simply opens the file with LockNote on their PC, enters the password, and can then read the message.

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LockNote is arguably the simplest encryption application available. If ease of use is paramount, it is an excellent choice.

4t HIT Mail Privacy Lite: Conceal Messages Within Images

Historically, reports surfaced of terrorists using images to transmit encrypted messages. It’s safe to assume that intelligence agencies were utilizing this technique long before its discovery by others.

If you wish to employ a more sophisticated encryption method, consider installing 4t HIT Mail Privacy Lite.

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I find this application particularly appealing due to its unique functionality. Open any image with the software in "Create Mode", apply a password and your message, and save it as a .bmp, .hit, or .zip file.

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Saving in bitmap mode ensures that, during transmission, all recipients will see is an image. When the recipient opens the image with the application, they simply enter the password, and the embedded message will appear under "Decrypted text".

These five encryption solutions should provide ample assistance when seeking to secure files before emailing them. While encryption isn’t always foolproof, implementing these measures demonstrates a commitment to protecting sensitive information.

Experiment with these applications to encrypt files for email, and share your experiences. Which one do you prefer? Please share your thoughts in the comments below.

Image Credit : Shutterstock

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