Step 1: Outlook's S/MIME

The most common form of mail encryption used in Microsoft Outlook is Outlook's own S/MIME encryption, which can be used to sign or encrypt e-mail (or both). When you sign a message with your key, it can be verified against your key to ensure that you did indeed create and send the message in question. However, S/MIME requires a certificate issued by a proper certification authority to work correctly.

If your organization has Windows 2000 Server or Windows Server 2003 with Certificate Services installed, you can generate certificates yourself for signing e-mail. You can also buy certificates from a certification authority, such as VeriSign. However, many people don't have the option of generating or buying certificates, usually because the cost is prohibitive. In such a case, you can use free tools to sign and encrypt e-mail using a system called public/private keys.

Simple e-mail encryption

 Home: Introduction
 Step 1: Outlook's S/MIME
 Step 2: Public keypairs
 Step 3: GnuPG and WinPT: Setup
 Step 4: Encrypting e-mail in WinPT
 Step 5: Verifying signed e-mail in WinPT
 Step 6: Extras: Symmetric encryption and hotkey commands

More information from

  • Whitepaper: Contributing to regulatory compliance with e-mail encryption
  • Opinion: How much encryption is enough?

    Serdar Yegulalp is editor of the Windows Power Users Newsletter. Check it out for the latest advice and musings on the world of Windows network administrators -- and please share your thoughts as well! Copyright 2005 TechTarget

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