Secure Windows Mail and digital IDs

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Windows Vista :: Secure Windows Mail and digital IDs ::

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Digital IDs Click this button to display the Certificates dialog box discussed in the section “Using Digital Certificates” in Article 2.

Get Digital ID Click this button to open a browser window containing information from the Microsoft website on where to obtain a digital certificate.

Encrypt Contents and Attachments for All Outgoing Messages Select this check box if you want to try to encrypt all the messages and attachments you send. You need to have the recipient’s certificate in your Contacts list in order to send an encrypted message or attachment. If you select this option and send messages or attachments to people whose digital certificates you don’t have, Windows Mail warns you of the problem and offers you the choice of sending the item without encryption or canceling sending it.

Digitally Sign All Outgoing Messages Select this check box if you want to digitally sign all the messages you send. To choose advanced security settings, click the Advanced button. Windows Mail displays the Advanced Security Settings dialog box , which offers the following options:

Warn on Encrypting Messages with Less than This Strength drop-down list Select the minimum acceptable level of encryption for messages: 40 bits, 56 bits, 64 bits, 128 bits, or 168 bits. See the next sidebar for an explanation of the bit-ness of encryption - but basically, the higher the number, the more secure. Windows Mail then warns you if you’re about to send a message with a lower level of encryption.

Always Encrypt to Myself When Sending Encrypted Mail Select this check box if you want Windows Mail to encrypt with your digital certificate the copy of the message that it puts in your Sent Mail folder. If you don’t encrypt this copy, you won’t be able to read it.

Include My Digital ID When Sending Signed Messages Select this check box to send your digital certificate with a digitally signed message so that the recipient can use the public key to read it. If the recipient already has your public key, you don’t need to send the digital certificate again.

Encode Message Before Signing Opaque Signing Select this check box if you want to encode your digitally signed messages in order to keep the signature secure. If you use this option, the recipient’s e-mail program must support S/MIME. Otherwise, they won’t be able to read the message.

Add Senders’ Certificates to My Windows Contacts Select this check box to have Windows Mail automatically add certificates from messages you receive to your Contacts list. This option is usually a good way to build your collection of certificates so that you can gradually send secure messages to more people assuming you want to do so.

Check for Revoked Digital IDs list Select the Only When Online option button or the Never option button to specify when to check that digital IDs you receive are current and haven’t been revoked. Click the OK button. Windows Mail closes the Advanced Security Settings dialog box and returns you to the Options dialog box.

Should You Use Encryption? And if So, How Much?

Internet e-mail is inherently insecure, because it passes through a shared medium the Internet. The standard analogy used to illustrate the insecurity of Internet e-mail is that of a postcard sent through the mail: At any point, anyone who can get hold of it can read its contents. Conversely, anyone looking for that particular postcard would have a hard time finding it among all the other mail being sent unless they were able to intercept it close to its source or its destination.

So the standard advice goes that you shouldn’t write anything in an unencrypted e-mail that you wouldn’t mind the whole world reading, because anyone who reads the e-mail could publish it worldwide almost instantly by posting it on a website or to a newsgroup. The recipient could also do this, but presumably you trust them enough to read the content of the message.

There’s much truth in this, but most people send unencrypted e-mail all day long without suffering any adverse consequences. However, if you want to make sure that nobody who intercepts a message can read it, you need to secure the message by using encryption.

As you saw a page or so ago, Windows Mail offers various strengths of encryption: 40 bit, 56 bit, 64 bit, 128 bit, and 168 bit. Which should you use?

Very generally speaking, the more bits, the more secure the encryption, and the more processing power it takes to encode and decode. The weakest encryption strengths, 40 bit and 56 bit, used to be the strongest encryption the U.S. government allowed software firms to export. Unlike with beer, exportstrength encryption is weaker than the normal article. The next strength, 64-bit encryption, is marginally stronger than 40-bit and 56-bit, but probably not enough so to be worth using if you’re concerned about security. While 128-bit encryption is considered strong encryption, if you want as much protection as possible, you should go straight to the 168-bit level.

Connection Page Options

The Connection page of the Options dialog box contains only three options:

Ask Before Switching Dial-up Connections Select this check box if you want Windows Mail to check with you before switching from a connection that isn’t working to another connection. If you have only one dial-up connection, you don’t need to worry about this setting.

Hang Up After Sending and Receiving Select this check box if you want Windows Mail to hang up your dial-up connection once it has finished sending and receiving mail when you issue a Send and Receive command. This setting is most useful with pay-as-you-go Internet connections.

Change button Click this button to display the Connections page of the Internet Properties dialog box discussed in the section “Preventing Internet Explorer from Connecting Automatically” in Article 2.

Advanced Page Options

The Advanced page of the Options dialog box lets you configure an assortment of settings.

Contact Attachment Conversion

Choose what you want Windows Mail to do with attachments.

• Select the Always Convert Contacts Attachments to vCard option button if you want to create vCards that you can use not only with Windows Vista but also with earlier versions of Windows.

• Select the Ask Me Every Time option button if you want Windows Mail to prompt you to decide each time you receive a vCard.

• Select the Leave Contact Attachments in Contact Format if you want Windows Mail to leave the attachments in the Contact format. This format is compatible with Windows Vista but not with earlier versions of Windows.

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