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Step 1: Outlook's S/MIME

Here is a guide to take you step-by-step to easy e-mail encryption focusing on the most common type: Microsoft 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


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This was last published in November 2005

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