The 5 Best Ways To Easily & Quickly Encrypt Files Before Emailing Them [Windows]

Ryan Dube 10-11-2011

encrypt files to emailEarlier this year, I was faced with a situation where I had a writer working for me overseas in China, where we were both certain that all of our email communications were being monitored. I resorted to using a fully-fledged encrypted email system called VaultletSuite Exchange Secure & Encrypted Emails With VaultletSuite As I was working through writing applications for my site, I came across a reporter who was in a country with a very rigid dictatorship. I went out in search of a free solution that... Read More where both of us had to install the client on our PCs. While it appeared to be very secure, it was also a bit cumbersome to have to log into a special email client just for my communications with one person.


If you are ever faced with a situation where you feel your communications might be monitored, a somewhat simpler and easier approach would be to encrypt files to email them to the person you’re communicating with. If they know the password, then they’ll be able to decrypt and open those files.

5 Ways to Encrypt Files Before Emailing Them

Encrypting files isn’t new. Tina covered this briefly in 2008 Become a Secret Steganographer: Hide and Encrypt your Files Read More , and we’ve also covered other apps that encrypt folders and drives like Mark’s review of TrueCrypt Encrypt Your USB Stick With Truecrypt 6.0 Read More or my review of AxCrypt Encrypt Or Completely Wipe Files With the Axcrypt Encryption Utility [Windows] There are plenty circumstances people may need to send an encrypted file, such as academic researchers sharing highly-sensitive information with each other over the Internet, corporate communications, or just friends that are discussing very private... Read More .

The field of cryptography extends back into ancient Greece, where the Spartans used ciphers to communicate hidden messages. Cryptography today consists of a dizzying array of algorithms that software applications can use to encrypt password-protected files in a way that is nearly impossible to decipher. I say nearly – because there is always an exception to the rule.

Use Encrypt Files To Quickly Protect Files

All of the solutions I’m going to offer in this article are applications that both you and the recipient install on your computers. On your end, the software will encrypt files or messages using a password you supply, and the recipient can use the software to decrypt that information.

Encrypt Files is an example of one of the easiest applications you can use to accomplish that task.


encrypt files to email

All you have to do is select the files that you want to encrypt, and click on “Encrypt” in the left panel. You’ll be prompted for the password you want to use to encrypt those files.

encrypt files to email freeware

Afterwards, a new copy of that file will appear that is encrypted. You can tell the software to use one of 13 cryptography algorithms, and you can tell it to either leave, delete or shred the original files.


Drag, Drop & Encrypt With dsCrypt

The fastest solution I’ve ever seen to quickly encrypt files is a small freeware app called dsCrypt.  When you run the dsCrypt executable, a small window will appear on your screen. All you have to do is drag files into the gray box. The program will prompt you for the password you want to use.

encrypt files to email freeware

The files will transform into encrypted .dsc files. The recipient just has to drop the .dsc files into the gray box, type the correct password, and the files will be decrypted and made usable again. I doubt the encryption is anything stellar, but for simple applications this gets the job done.

Encrypt Files Or Email With MEO Encryption

Another file encryption app that I really like a lot is MEO Encryption. This is free encryption software that not only encrypts and decrypts files, but it also lets you send encrypted email messages as well.


encrypt files to email freeware

File encryption also includes a feature where you can save files to a self-extracting executable.

The 5 Best Ways To Easily & Quickly Encrypt Files Before Emailing Them [Windows] fileencrypt4

The beauty of this is that the person you’re sending it to doesn’t need to install any software, they just need the correct password. The feature that I love about this software is that you can configure it to use any SMTP account and the software will encrypt email messages and send them directly for you.


encrypt files

Only two crypto algorithms are available, a light one (for fast encryption) and a strong one (for slow encryption). Choose according to your needs.

Use LockNote To Send Encrypted Simple Text

One solution to send text messages that are protected from prying eyes is by writing a message in a text file using LockNote, and then saving it in an encrypted format.  The application feels pretty much identical to Windows Notepad, but when you save the file, you’ll be prompted for a password.

encrypt files

When your recipient runs LockNote on their PC, all they have to do is open the file, answer the password request, and they can read your message.

encrypt files

This is probably the simplest encryption application I’ve ever seen. If ease of use is your priority, I’d highly suggest LockNote.

Encrypt Messages Into Images

Years ago, it hit the news that terrorists were using images to send encrypted messages. You can be sure that most covert intelligence agents were using that technology long before terrorists ever discovered it.

If you want to elevate your encryption efforts into the field of image encryption, then you may want to install 4t HIT Mail Privacy Lite.

The 5 Best Ways To Easily & Quickly Encrypt Files Before Emailing Them [Windows] fileencrypt8

I have to be honest, this is probably my favorite app, simply because of the coolness factor. Open any image with the software in “Create Mode“, apply a password and a message, and then save it as a .bmp, .hit. or a .zip file.

encrypt files to email

If you save in bitmap mode, in transit all anyone will see is a picture. When the recipient opens the picture with this app, all they have to do is type the password and the embedded message will appear under “Decrypted text“!

Hopefully, these five encryption solutions offer you plenty of help when you’re looking for a way to encrypt files before emailing them off to folks. Encryption isn’t always foolproof – there’s always someone out there that can break encryption, but at least you can rest assured that you’ve at least tried your best to protect sensitive information as best you could.

Give these apps a try to encrypt files to email, and let us know if they worked out well for you. Which one is your favorite? Share your thoughts in the comments section below.

Image Credit : Shutterstock

Related topics: Email Tips, Encryption.

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  1. Bill
    October 15, 2016 at 9:55 pm

    I found Encrypt Files too Slow. Slow in opening and after you open it, the program takes forever to list the contents of your hard drive. It seems to lock up, you can't even close it until it is finished listing all your folders. Then when you click on a Folder the process starts all over again.

  2. nailtrail
    June 14, 2016 at 3:58 pm

    3-DES as strong crypto, that's funny. Why recommend terribly outdated software when there are better alternatives out there?

  3. pat
    March 3, 2016 at 12:22 pm

    encrypted e-mail are usually a virus !

  4. bobby mcbobson
    January 29, 2016 at 12:47 am

    does anyone want to be the jesse pinkman to my walter white

  5. bobby mcbobson
    January 29, 2016 at 12:46 am

    there is a snake in my boot

  6. Marco Torez
    January 13, 2016 at 2:44 pm

    Do smb know how to send and receive encrypted files without desktop apps? Just like a service on the website?

  7. Anonymous
    October 21, 2015 at 8:14 am

    Personally, I find Cloak Apps by Clault much easier. It uses public key encryption to protect your files. Saves the hassle of remembering passwords.

  8. Anonymous
    July 11, 2015 at 6:55 pm

    Is there a newer version of this article? I would be happy, you give CrococryptFile or CrococryptMirror a try (both freeware, CFile open-source, tool):


  9. Specky
    February 3, 2015 at 1:32 am

    you can also just rename the file extension, this makes it impossible to open for anybody who doesnt know what filetype it is.
    Just make sure that you dont tell the recepient the filetype in the same email.

  10. psy
    January 7, 2015 at 6:11 pm

    Would you have a recommendation onhow to send encrypted audio files to China?

    • Laura
      March 16, 2015 at 2:06 pm

      I can recommend Prot-On. It is a free software. You can encrypts audio and video files and decide who and when access them.

  11. Stevieg21
    November 10, 2011 at 7:43 pm

    Any compression program will let you encrypt a file or group of files.  i.e. 7-Zip, WinRar, WinZip, PeaZip...

    • Ryan Dube
      November 13, 2011 at 5:38 pm

      True, however in most cases the encryption is rather weak.

      • Stevieg21
        November 14, 2011 at 1:41 am

        For the purpose of quickly encoding them to send as an e-mail attachment they are fine.  I like 7-Zip since it will encrypt the file names as well for added security.  It uses AES 256 bit encryption.

    • Ed Dems
      November 24, 2011 at 3:04 am

      True enough. Lots of people have those programs. 

  12. Anonymous
    November 10, 2011 at 6:22 pm

    For Windows to Windows, I use LockNote and it's great.

    But, do you know of any solution that would allow someone reading his email in Android to decrypt the file? I haven't been able to find anything yet.

    • Ryan Dube
      November 13, 2011 at 5:39 pm

      Hi HildyJ - I am not sure, but you might post that question in MUO Answers. Maybe someone out there knows of such an Android app.

  13. Optombvpu
    November 10, 2011 at 6:18 pm

    thank you so much for this post, it helped me a lot...i loved MEO encryption

    • Ryan Dube
      November 13, 2011 at 5:40 pm

      Excellent - glad the article helped! Thanks for your feedback.