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Microsoft Outlook 2010 : Understanding Messaging Protocols and Standards, Security Provisions in Outlook

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12/12/2012 5:59:44 PM

1. Understanding Messaging Protocols and Standards

A messaging protocol is a mechanism that messaging servers and applications use to transfer messages. Being able to use a specific email service requires that your application support the same protocols the server uses. To configure Outlook 2010 as a messaging client, you need to understand the various protocols supported by Outlook 2010 and the types of servers that employ each type. The following sections provide an overview of these protocols.

SMTP/POP3

Simple Mail Transport Protocol (SMTP) is a standards-based protocol used for transferring messages and is the primary mechanism that Internet- and intranet-based email servers use to transfer messages. It's also the mechanism that Outlook 2010 uses to connect to a mail server to send messages for an Internet account. SMTP is the protocol used by an Internet email account for outgoing messages.

SMTP operates by default on TCP port 25. When you configure an Internet-based email account, the port on which the server is listening for SMTP determines the outgoing mail server setting. Unless your email server uses a different port, you can use the default port value of 25. If you want to use Outlook 2010 for an existing Internet mail account, confirm the SMTP server name and port settings with your ISP.

POP3 is a standards-based protocol that clients can use to retrieve messages from any mail server that supports it. Outlook 2010 uses this protocol when retrieving messages from an Internet- or intranet-based mail server that supports POP3 mailboxes. Nearly all ISP-based mail servers use POP3. Exchange Server also supports the use of POP3 for retrieving mail.

POP3 operates on TCP port 110 by default. Unless your server uses a nonstandard port configuration, you can leave the port setting as is when defining a POP3 mail account.

IMAP

Like POP3, IMAP is a standards-based protocol that enables message transfer. However, IMAP offers some significant differences from POP3. For example, POP3 is primarily designed as an offline protocol, which means that you retrieve your messages from a server and download them to your local message store (such as your local Outlook 2010 folders). IMAP is designed primarily as an online protocol, which allows a remote user to manipulate messages and message folders on the server without downloading them. This is particularly helpful for users who need to access the same remote mailbox from multiple locations, such as home and work, using different computers. Because the messages remain on the server, IMAP eliminates the need for message synchronization.

Tip

INSIDE OUT Keep POP3 messages on the server

IMAP by default leaves your messages on the server. If needed, you can configure a POP3 account in Outlook 2010 to leave a copy of messages on the server, allowing you to retrieve those messages later from another computer. (To learn how to configure a POP3 account, on page 160.) IMAP offers other advantages over POP3 as well. For example, with IMAP, you can search for messages on the server using a variety of message attributes, such as sender, message size, or message header. IMAP also offers better support for attachments because it can separate attachments from the header and text portion of a message. This is particularly useful with multipart Multipurpose Internet Mail Extensions (MIME) messages, allowing you to read a message without downloading the attachments so that you can decide which attachments you want to retrieve. With POP3, the entire message must be downloaded.

Security is another advantage of IMAP because it uses a challenge-response mechanism to authenticate the user for mailbox access. This prevents the user's password from being transmitted as clear text across the network, as it is with POP3.

IMAP support allows you to use Outlook 2010 as a client to an IMAP-compliant email server. Although IMAP provides for server-side storage and the ability to create additional mail folders on the server, it does not offer some of the same features as Exchange Server, or even POP3. For example, you can't store contact, calendar, or other nonmessage folders on the server. Also, special folders such as Drafts and Deleted Items can't be stored on the IMAP server. Even with these limitations, however, IMAP serves as a flexible protocol and surpasses POP3 in capability. Unless a competing standard appears in the future, it is possible that IMAP will eventually replace POP3. However, ISPs generally like POP3 because users' email is moved to their own computers, freeing space on the mail server and reducing disk space management problems. For that reason alone, don't look for IMAP to replace POP3 in the near future.

MAPI

MAPI is a Microsoft-developed application programming interface (and) that facilitates communication between mail-enabled applications. MAPI support makes it possible for other applications to send and receive messages using Outlook 2010. For example, some third-party fax applications can place incoming faxes in your Inbox through MAPI. As another example, a third-party MAPI-aware application could read and write to your Outlook 2010 Address Book through MAPI calls. MAPI is not a message protocol, but understanding its function in Outlook 2010 helps you install, configure, and use MAPI-aware applications to integrate Outlook 2010.

LDAP

Lightweight Directory Access Protocol (LDAP) was designed to serve with less overhead and fewer resource requirements than its precursor, Directory Access Protocol. LDAP is a standards-based protocol that allows clients to query data in a directory service over a Transmission Control Protocol (TCP) connection. For example, Windows Server uses LDAP as the primary means for querying AD DS. Exchange Server supports LDAP queries, allowing clients to look up address information for subscribers on the server. Other directory services on the Internet employ LDAP to implement searches of their databases.

Like Outlook Express, Windows Mail, and Windows Live Mail, Outlook 2010 allows you to add directory service accounts that use LDAP as their protocol to query directory services for email addresses, phone numbers, and other information regarding subscribers.


RSS

Real Simple Syndication (RSS) is a set of web feed formats that enable publishing and updating of frequently updated content. Outlook 2010 can function as an RSS feed reader, pulling in news items, blog posts, and other data from online sites and services that offer the RSS feeds. 

MIME

MIME is a standard specification for defining file formats used to exchange email, files, and other documents across the Internet or an intranet. Each of the many MIME types defines the content type of the data contained in the attachment. MIME maps the content to a specific file type and extension, allowing the email client to pass the MIME attachment to an external application for processing. For example, if you receive a message containing a WAV audio file, Outlook 2010 passes the file to the default WAV file player on your system.

S/MIME

Secure/Multipurpose Internet Mail Extensions (S/MIME) is a standard that allows email applications to send digitally signed and encrypted messages. S/MIME is therefore a mechanism through which Outlook 2010 permits you to include digital signatures with messages to ensure their authenticity and to encrypt messages to prevent unauthorized access to them.

MHTML

MIME HTML (MHTML) represents MIME encapsulation of HTML documents. MHTML allows you to send and receive web pages and other HTML-based documents and to embed images directly in the body of a message instead of attaching them to the message. See the preceding two sections for an explanation of MIME.

iCalendar, vCalendar, and vCard

iCalendar, vCalendar, and vCard are Internet-based standards that provide a means for people to share calendar information and contact information across the Internet. The iCalendar standard allows calendar and scheduling applications to share free/busy information with other applications that support iCalendar. The vCalendar standard provides a mechanism for vCalendar-compliant applications to exchange meeting requests across the Internet. The vCard standard allows applications to share contact information as Internet vCards (electronic business cards). Outlook 2010 supports these standards to share information and interact with other messaging and scheduling applications across the Internet.

2. Security Provisions in Outlook

Outlook 2010 provides several features for ensuring the security of your data, messages, and identity. This section presents a brief overview of security features in Outlook 2010 to give you a basic understanding of the issues involved, with references to other locations in the book that offer more detailed information about these topics.

Protection Against Web Beacons

Many spammers (people who send unsolicited email) use web beacons to validate email addresses. The spammers send HTML-based email messages that contain links to external content on a website (the web beacon), and when the recipient's email client displays the remote content, the site validates the email address. The spammer then knows that the address is a valid one and continues to send messages to it.

Outlook 2010 blocks web beacons, displaying a red X instead of the external image. You can view blocked content selectively, on a per-message basis, or you can configure Outlook 2010 to view all content but control access to HTML content in other ways. You can also turn off web beacon blocking, if you want, and control external HTML content in other ways.

Attachment and Virus Security

You probably are aware that a virus is malicious code that infects your system and typically causes some type of damage. The action caused by a virus can be as innocuous as displaying a message or as damaging as deleting data from your hard disk. One especially insidious form of virus, called a worm, spreads itself automatically, often by mailing itself to every contact in the infected system's address book. Because of the potential damage that can be caused by viruses and worms, it is critically important to guard against malicious code entering your system.

There are multiple possible points of defense against viruses and worms. For example, your network team might deploy perimeter protection in the form of one or more firewalls that scan traffic coming into your network and leaving it. Your mail administrators might have virus protection at the server level. You probably have a local antivirus client that checks the files on your computer and potentially also checks attachments that come into your Inbox. All of these are important options for protecting your network and your computer from infection.

Caution

Your virus scanner is only as good as its definition file. New viruses crop up every day, so it's critical that you have an up-to-date virus definition file and put in place a strategy to ensure that your virus definitions are always current.

Most viruses and worms propagate through email attachments, so to provide protection against them, Outlook 2010 controls how attachments are handled, blocking certain types of files (such as program executables) from being opened at all. For selected other files that offer less risk, Outlook requires you to save the file to disk and open it from there, rather than from Outlook. These behaviors and the types of files applicable for each can be controlled either by the end user or by an administrator, depending on your environment.

An additional security feature that is new in Office 2010 is Protected View. When you open an attachment that is an Office file type (a Microsoft Word document, a Microsoft Excel spreadsheet, etc.), the document opens in a separate sandbox instance of the application. For example, assume that you have Word open and are working on a document that you created. Then, you switch over to Outlook and open a Word document that arrived as an attachment to an email. Word opens a separate version to display that attachment, but this sandbox version of Word operates with greater restrictions and fewer rights and privileges than the version that you are using to modify your own document. You can't save the file or edit it while it is running in this version, so the application displays a banner across the top labeled Protected View (see Figure 1), and provides a button labeled Enable Editing that, when clicked, enables you to edit the document, save it, and so on.

Protected View is actually a separate, lower-privileged instance of the application.

Figure 1. Protected View is actually a separate, lower-privileged instance of the application.

The combination of attachment blocking and Protected View will protect your computer from a wide variety of potential threats, but that combination can't protect against all threats. For that reason, you should ensure that you have an updated antivirus client running on your computer as well as at your mail server. Adding protection at the perimeter of the network is a good idea as well.

Digital Signatures

Outlook 2010 allows you to add a certificate-based digital signature to a message to validate your identity to the message recipient. Because the signature is derived from a certificate that is issued to you and that you share with the recipient, the recipient can be guaranteed that the message originated with you, rather than with someone trying to impersonate your identity.

In addition to signing your outgoing messages, you can use secure message receipts that notify you that your message has been verified by the recipient's system. The lack of a return receipt indicates that the recipient's system did not validate your identity. In such a case, you can contact the recipient to make sure that he or she has a copy of your digital signature.

Note

Although you can configure Outlook 2010 to send a digital signature to a recipient, there is no guarantee that the recipient will add the digital signature to his or her contacts list. Until the recipient adds the signature, digitally signed messages are not validated, and the recipient cannot read encrypted messages from you.

Message Encryption

Where the possibility of interception exists (whether someone intercepts your message before it reaches the intended recipient or someone else at the recipient's end tries to read the message), Outlook 2010 message encryption can help you keep prying eyes away from sensitive messages. This feature also relies on your digital signature to encrypt the message and to allow the recipient to decrypt and read the message. Someone who receives the message without first having the appropriate encryption key from your certificate installed on his or her system sees a garbled message.

 
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