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March 26, 2010 02:26 PM

Prevent Problems with Exchange Server 2010's MailTips

New feature can help save time and resources
Windows IT Pro
InstantDoc ID #104680
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When a new version of Microsoft Exchange Server appears, administrators are often excited by its new features, but users are typically often left cold because they see no value from those features. However, MailTips is a new feature in Exchange Server 2010 that delivers real value to users, providing they use a client that supports MailTips, which is currently Microsoft Outlook 2010 and Outlook Web App (OWA) 2010. The idea behind MailTips is to provide users with immediate feedback to help users save time and help IT save system resources. The value of this idea is so obvious that it's surprising that it took so long for this feature to appear. After I explain why MailTips are valuable and how they work, I'll show you how to configure them.

 Taking a Proactive Stance

In early email systems, sending a message was a "send and forget" affair. You dispatched a message into the void and hoped that it arrived. As time went by, features such as out-of-office notices, delivery and read receipts, and nondelivery notifications were incorporated to give users feedback as to what happened to messages after they were sent. Exchange 2010 introduces a variation on the theme with a feature called delivery reports that lets users see the path of a message within an Exchange organization, including the expansion of distribution groups into individual members, delivery to servers, and delivery to external connectors for transmission to other email systems. However, worthy as these features are, they're all after the fact. Messages have to be sent before users can be informed that the message has been delivered, that someone is out of the office, or that the message wasn't delivered.

Enter MailTips, a new web service designed to provide users with feedback about common problems before a message is sent. The idea is that by being proactive and warning users that messages might not be delivered or read, users will be more productive and less likely to call the Help desk to complain that their email didn't arrive. Plus, MailTips can reduce system resource usage by eliminating the need to process messages that will fail.

Table 1 lists some common conditions when MailTips are useful.

Potential Problem

Action

Message addressed to recipient that's out of the office

If an out-of-office notice is set for a mailbox, the user is told that the recipient is away and has the choice to remove that person from the message. MailTips displays the first 250 characters of an out-of-office notice.

Message addressed to a very large distribution

If a message is addressed to a distribution that has more recipients than the large-audience limit configured for the organization, MailTips tells the user how many people will receive the message (per group and in total). Duplicate addressees aren't removed, so the overall total might be a little higher than the actual number of messages that are generated, but it's a good guide to stop users from sending messages that result in hundreds of deliveries. Exchange doesn't attempt to process individual MailTips for messages that are addressed to more than 200 recipients, as this would impose an unacceptable performance overhead on the CAS server. For the same reason, when a user addresses a message to a distribution group, Exchange doesn't evaluate individual MailTips for the group members. The exception is that Exchange will show the number of external recipients if there are any in the group.

Message addressed to a non-existent recipient

Messages can linger in mailboxes for a long time and might contain addresses that are no longer valid. Invalid addresses can also persist in Outlook's auto-complete list. MailTips detects this condition and lets the user remove the obsolete recipient before sending the message, thereby eliminating a nondelivery notification.

Message addressed to an external recipient

If a message is addressed to someone outside the organization or a group that contains an external recipient, MailTips warns the user in case the message contains confidential company information.

Reply to Bcc

If users reply to a message in which they're on the Bcc list, MailTips notifies them about being blindly copied and lets them know that if they reply, the other recipients will know they received the original message.

Oversized message

If users attempt to send a message that exceeds the maximum message size for the organization or for one of the message recipients, MailTips tells them that Exchange won't deliver the message. MailTips can't warn users that an external organization will have problems with an oversized message.

Message addressed to a moderated group

Messages sent to a moderated group have to be approved by the moderator, so MailTips warns the user that there might be a delay before the message is okayed. Moderators of the group or anyone explicitly allowed to receive messages addressed to the group won't see this MailTip.

Message addressed to a restricted recipient

Administrators can configure mailboxes and groups so that only certain users can send them messages. If unauthorized users attempt to send a message to a restricted recipient, MailTips warns them that their message won't be accepted.

 As you can see, in most cases, MailTips stop users from doing something that wastes time and causes frustration or something that reduces traffic for Exchange. Warning users about sending a message to a very large distribution is useful because they often don't realize that it will cause Exchange to deliver the message to thousands of mailboxes. People who receive the message can cause a mail storm by using Reply to All to generate a response that goes to everyone and provokes even more responses. The net result is usually a Hub Transport server that's swamped with traffic, large message queues, and slow delivery of other mail.

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