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Different mail protocols have different levels of security. The default settings for most web hosts now include more secure protocols than the traditional POP and SMTP protocols. Mail.app has also been set up to allow for more protection of passwords in transit and more secure encryption protocols.
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Secure Sockets Layer (SSL) is a protocol developed by Netscape for transmitting private documents via the Internet. SSL works by using a private key to encrypt data that s transferred while en route to another system. Both Safari and Firefox support SSL, and many web sites use SSL to secure confidential user information, such as credit card numbers for submissions over the Internet.
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CHAPTER 5 SE CURING WEB BROWS ERS AND E-MA IL
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The most notable form of protecting passwords in transit is employing SSL. Transport Layer Security (TLS) is actually the successor of the SSL 3.0 protocol. These protocols are common when securing password submissions and other network traffic while the data is passing over the unknown elements of the Internet. Although SSL and TLS are similar and your system can support using both, it is worth noting that they cannot be used on web servers concurrently.
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Note By convention, URLs that require an SSL connection start with https, not http.
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Note Web sites typically use port 443 for SSL. However, when you are using SSL with other protocols
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such as IMAP, the port can be different. Figure 5-10 shows an example of how IMAP uses port 995 when secured using SSL.
Figure 5-10. An Apple mail account s advanced settings Sometimes with SSL you ll be asked to verify the authenticity of a server every time you open your e-mail client. This often has to do with the SSL certificate of your mail host being self-assigned. Self-assigned SSL certificates typically need to manually be trusted when you are visiting a site. If you choose not to trust a certificate, then SSL will not allow you to communicate over the secure channel to that host.
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Note If you are required to accept the certificate every time you visit a site, then you can add the site as
an x509 anchor in Safari by opening the Keychain Access utility and dragging the certificate into the X509 dialog box.
Now that your communications have been protected using SSL, let s look at how your password is actually sent over the wire. POP is a protocol used for downloading mail from a mail server. IMAP is a protocol used to synchronize mail between a mail client and a mail server. POP and IMAP are merely protocols for accessing data; they do not tell a client how to actually authenticate into the remote host. For this, there are a variety of protocols including MD5, NTLM, KPOP, APOP, GSSAPI, Kerberos, and Password (PlainText). In the realm of layered security, the most important thing to know here is that you need to contact your mail provider and find out exactly what protocols are supported. If it does not support a protocol, you will not be able to use it.
Note Oftentimes the only way to get your Internet service provider to introduce support for a new protocol
is to request it. When enough people speak up, the ISP will find a way to support what its users want.
The options for securing your mail password include the following: MD5: Message Digest 5 (MD5) is a secure hashing function that converts an arbitrarily long data stream into a digest of fixed size. By breaking up messages and encrypting them, they are sent more securely. NTLM: This is common in more Windows-oriented environments, such as with Microsoft Exchange. Kerberized POP: POP is able to use Kerberos to access your servers. Kerberized POP can help more fully integrate your single sign-on environment. For more on Kerberos, please see 14. Authenticated POP: An extension of the POP3 protocol, APOP encrypts both the username and the password. Kerberos Version 5 (GSSAPI): This uses the latest version of Kerberos to encrypt e-mail and then authenticates the e-mail account against a directory server. Kerberos Version 4: This is similar to Kerberos Version 5, but one version back. Password: This is standard password authentication. Some of these same authentication options are configurable in the SMTP settings, as shown in Figure 5-11. Keep in mind that if your username and password for SMTP are the same as your information for POP and you use SSL for SMTP and not POP, then you are still exposing your passwords.
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