Email an encrypted .EXE file (AxCrypt) vs Email + PGP

AxCrypt is free and open source. This is beneficial because anyone can examine the source code and check for errors.

After selecting "Encrypt copy to .EXE," rename the file to ".EXE.TXT" in order to bypass email provider restrictions on sending .EXE files. Windows will then warn you that the file will become unusable but ignore it and continue to email the file. All the recipient needs to do upon arrival is rename the file back to .EXE and ignore the Windows warning message. Then simply open the self extracting file and type in the agreed upon password between the sender and recipient. This is a great advantage of AxCrypt because it does not force your recipient to download any software.

AxCrypt is an extremely convenient encryption program because it is always available at a single right click.

AxCrypt encrypts each file with a passphrase and an optional key-file. Transferring a key-file (that AxCrypt can generate for you) on a separate medium and the password on another medium to your recipient is the most secure option. Although a strong password alone will do. The only caveat is that the password and key file must be transferred to your recipient and the most secure way to transfer it is physically.

As long as you have the password or keyfile to your encrypted file then you can still access it. This is beneficial if the software ever becomes unsupported.

The original version of PGP is no longer freeware since it was aquired by Symantec, but the source code can still be downloaded for peer review.

PGP is a protocol and not an application per se. It offers a standard on which applications can implement to offer full encryption.

PGP uses asymmetric encryption. One user generates 2 keys - private and public. Another user uses the public key to encrypt the message that can then be decrypted only using first users's private key.