HOW TO: Encrypt Files Using PGP Desktop 8.x

Article:HOWTO41923  |  Created: 2006-03-14  |  Updated: 2011-02-06  |  Article URL http://www.symantec.com/docs/HOWTO41923
Article Type
How To




This article describes how to encrypt individual files using PGP 8.x.



Using PGP to encrypt individual files allows you to keep files stored in an encrypted state, or attach them to emails for secure transmission to others. There are several different ways to encrypt individual files. The public-key and conventional encryption methods will be defined and described in this article.

  • Public-Key Encryption - this form of file encryption uses a public key for encryption and a private key for decryption. This allows you to encrypt a file to someone's public key, which may only be decrypted by their private key, for which only they know the passphrase. This method of encryption is considered the most secure, but requires that you have a copy of the intended recipient's public key.
  • Conventional Encryption - this form of file encryption uses the same key for encryption and decryption. It allows you to encrypt a file to another PGP user without having their public key, by protecting the encrypted file with a passphrase (chosen at the time of encryption). However, the passphrase must then be communicated to the person who will decrypt the file. This method of encryption is less secure than public-key encryption, because more than one user must know the decryption passphrase.

Public-Key File Encryption 

  1. Right click on the file to be encrypted.
  2. Point to PGP, then click Encrypt or Encrypt & Sign. At this point the Key Selection Dialog appears.
  3. From the list of potential recipients in the top window, drag the intended recipient(s) to the bottom Recipients window.

    Note: If you will be emailing this as a binary file and are using an older email application, you may need to select the check box labeled 'Text Output' to save the file as ASCII text. This will increase the size of the encrypted file by about 30%.


  4. If you do not want to keep a copy of the original file, check the Wipe Original box (PGP will wipe the original file and leave only an encrypted copy of it).
  5. If the file may be vulnerable to a TEMPEST attack, check the box labeled Secure Viewer.
  6. Click OK. If you chose to sign the file as well, enter the passphrase for your private key when prompted. An encrypted copy of the file will now be created in the same directory as the original.

Conventional File Encryption 

  1. Right click the file to be encrypted.
  2. Point to PGP, then click Encrypt or Encrypt & Sign. At this point the Key Selection Dialog appears.
  3. Check the box labeled Conventional Encryption.
  4. If you will be emailing this as a binary file and are using an older email application, you may need to select the check box labeled 'Text Output' to save the file as ASCII text. This will increase the size of the encrypted file by about 30%.
  5. If you do not want to keep a copy of the original file, check the Wipe Original box (PGP will wipe the original and leave only an encrypted copy of it).
  6. If the file may be vulnerable to a TEMPEST attack, check the box labeled Secure Viewer.
  7. Click OK.
  8. Enter and confirm a passphrase for the encrypted file, then click OK. If you chose to sign the file, enter the passphrase for your private key, then click OK again. An encrypted copy of the file will now be created in the same directory as the original.
  • The aforementioned public-key and conventional encryption methods may also be accessed from the PGPmail toolbar by clicking the Encrypt or Encrypt & Sign buttons, whose icons appear on the PGPmail toolbar as a lock/envelope and a lock/pencil/envelope respectively.
  • If you wish to encrypt the body of a file while it is still open on your screen (as opposed to saving the file and right clicking its icon to encrypt), you may use either the Current Window or Clipboard features. These features and their usage are described in detail below.

Current Window Encryption 

PGP's Current Window encryption feature allows you to encrypt the text of whatever window is the 'current window' on your screen at the moment. This feature is accessible by clicking your PGPtray icon(gray or gold padlock in system tray).

  1. Make sure the window--whose body of text you wish to encrypt--is the foremost window on your screen.
  2. Click the PGPtray icon in your system tray (gray or gold padlock).
  3. Point to Current Window.
  4. Click Encrypt or Encrypt & Sign.
  5. If you will be using conventional encryption, check the box labeled Conventional Encryption; otherwise drag the intended recipient(s) to the bottom Recipients window.
  6. If the file may be vulnerable to a TEMPEST attack, check the box labeled Secure Viewer.
  7. Click OK.
  8. If you chose conventional encryption, enter and confirm a passphrase for the file, then click OK. If you chose to sign the file, enter the passphrase for your private key and click OK.

Clipboard Encryption 

PGP's Clipboard encryption feature allows you to encrypt data which has been copied to the Windows Clipboard. Thus when you paste the information from the clipboard, it is pasted as encrypted text.

  1. Copy the text which you desire to encrypt.
  2. Click the PGPtray icon in your system tray (gray or gold padlock).
  3. Point to Clipboard
  4. Click Encrypt or Encrypt & Sign.
  5. If you will be using conventional encryption, check the box labeled Conventional Encryption; otherwise drag the intended recipient(s) to the bottom Recipients window.
  6. If the file may be vulnerable to a TEMPEST attack, check the box labeled Secure Viewer.
  7. Click OK.
  8. If you chose conventional encryption, enter and confirm a passphrase for the file, then click OK. If you chose to sign the file, enter the passphrase for your private key and click OK.
  9. Now paste the contents of the clipboard into a file to which you have write permission. At this point an encrypted PGP message should be pasted.

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