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Testing SMTP AUTH with Outlook Express
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To show how to test SMTP AUTH, I will set up an Outlook Express client to use SMTP AUTH to log in with a login name and password and perform a relay. If you do not have Outlook Express, you can use any e-mail client that is capable of authenticating outbound connections. Open Outlook Express, and select Tools Accounts... to edit the properties of an e-mail account. Click the Servers tab. At the bottom of this tab is an entry under Outgoing Mail Server. Highlight the option for My Server Requires Authentication, and click the Settings... button (see Figure 8-1).
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CHAPTER 8 s AUTHENTICATING AND SECURING YOUR MAIL
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Figure 8-1. Configuring Outlook Express to use SMTP AUTH
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Inside the Settings tab you have two options. You can tell Outlook to provide the same details it uses to log into your e-mail account (which should be your login name and password for your mail server if you use a local login), or you can specify another login and password, if you are using the sasldb authentication option. Click OK; when the dialog box appears, click OK again, and then click Close to shut down the Account Setup tab. Now send a test e-mail to an external e-mail address. If everything is set up correctly, you should see some resulting messages similar to those in Listing 8-31 in your mail log file. This example shows a successful TLS connection being created from your client and a successful SMTP AUTH authentication using the LOGIN method for username admin. Listing 8-31. Successful SMTP AUTH Authentication in Postfix Apr 8 14:50:35 puppy postfix/smtpd[30017]: connect from client.yourdomain.com[192.168.0.50] Apr 8 14:50:35 puppy postfix/smtpd[30017]: setting up TLS connection from client.yourdomain.com[192.168.0.50] Apr 8 14:50:35 puppy postfix/smtpd[30017]: TLS connection established from client.yourdomain.com[192.168.0.50]: TLSv1 with cipher RC4-MD5 (128/128 bits) Apr 8 14:50:35 puppy postfix/smtpd[30017]: 99C9F231E56: client= client.yourdomain.com[192.168.0.50], sasl_method=LOGIN, sasl_username=admin
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Sendmail Usenet and mailing list: http://www.sendmail.org/usenet.html Postfix mailing lists: http://www.postfix.org/lists.html Postfix TLS mailing list: http://www.aet.tu-cottbus.de/mailman/listinfo/ postfix_tls
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Sites
Sendmail: http://www.sendmail.org/ Postfix: http://www.postfix.org Postfix TLS patch: http://www.aet.tu-cottbus.de/personen/jaenicke/postfix_tls/ Postfix TLS RPMs: http://postfix.wl0.org/en/ Cyrus SASL: http://asg.web.cmu.edu/sasl/ S/MIME and PGP-MIME: http://www.imc.org/smime-pgpmime.html and http://www.ietf.org/html.charters/smime-charter.html
CHAPTER
Hardening Remote Access to E-mail
ore and more users expect to be able to access their e-mail remotely, including from home and while traveling. Even more users are best classified as roving users who do not regularly return to a home base and need to be able to access their e-mail resources remotely. These users are forced by the nature of their movements to rely on remote access to provide access to vital corporate resources such as e-mail. To address the requirement for remote access, several protocols were developed to provide remote-access functionality to a variety of resources. This chapter focuses on the protocols that give you remote access to your e-mail resources in the form of messages and message stores. The two key protocols I will cover are the Internet Message Access Protocol (IMAP) and the Post Office Protocol (POP); I will also cover a variety of related offshoots of these protocols. These protocols basically perform the same core function, providing remote access to your e-mail, but they perform that function using different methods. Naturally, the farther your users are from your internal network (especially as the medium of the Internet is interposed between your remote users and the resources they require), the higher the risk that your data (usernames, passwords, valuable commercial data) could be intercepted, diverted, or altered. Earlier implementations of remote-access protocols and systems assumed that the fabrics and networks those protocols were traveling across were much nicer and friendlier places than the current environment has proven to be. Additionally, opening connections to the Internet for these protocols to operate also puts your system at risk and adds points through which an attacker could attempt to penetrate your system. I will explain a bit about IMAP and POP Then I will make some recommendations about . particular servers I think are the most secure applications to provide this functionality. I will take you through the risks and potential exploits that running IMAP and POP exposes you to and then take you through installing, configuring, and securing an IMAP server and a POP server. I will also cover the commonly used Fetchmail tool and the security risks associated with using it, as well as how to mitigate some of the risks and harden your Fetchmail installation. I will not go into a lot of detail about non-security-related configuration and management issues such as performance.
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