Q: What are MailTips used for in Exchange 2010 with Outlook 2010?

A: Sometimes when you send email messages, you must maintain a little faith that they're going to reach their destination and be read, or at least accessed, in a reasonable timeframe. MailTips was added to Microsoft Exchange Server 2010 to provide insight for the sender before a message is sent, thus providing greater efficiency in corporate messaging. So, what information does MailTips provide?

Before we look at the answer to that question, there's a small limitation to MailTips to mention: It's available only in Outlook 2010 installations and Outlook Web App (OWA) in Exchange 2010. MailTips is fully enabled by default, but can be limited should administrators be required to do so. I can't imagine why they might, however. MailTips aren't resource-intensive. They're implemented as an Exchange Web Service queried from the client. The Client Access server retrieves necessary information from the Mailbox server and the Global Address List (GAL) and returns it to the client.

From an Outlook perspective, you configure MailTips by going to File, Options, then selecting Mail in the left pane of the Outlook Options menu. You then scroll down to MailTips, as Figure 1 shows. This section won't be present if Outlook 2010 isn't connected to an Exchange 2010 server.

Figure 1: Finding MailTips Options in Outlook 2010 (Click image for larger view)

The MailTips Options button opens the MailTips Options window that Figure 2 shows, revealing twelve MailTip items that can be toggled on or off. You can select specific MailTip items to show when their prerequisites exist, or you can turn them all off by checking the box beside Never display MailTips near the bottom of the MailTips Options window. I leave all options enabled in Outlook deployments.

Figure 2: Setting options for MailTips in Outlook 2010 (Click image for larger view)

Incidentally, MailTips for OWA is configured using the Exchange Management Shell. Entering the command

Get-OrganizationConfig | fl MailTips*

will return cmdlet options for MailTips.

The list of MailTips in the Options window is sensibly segmented into Sending Restrictions, Undeliverable Message, and Informational. Where there's a limitation, either based on message size or available mailbox storage quota, having MailTips advise the user before the message is transferred into the Exchange organization saves resources. It can also alleviate the frustration of receiving a nondelivery report (NDR) well after you thought the message should have been delivered.

The MailTips message might be based on conditions of the sender or the recipient mailbox. In Figure 3, a large attachment to a message will push the sender's mailbox past the mailbox quota allowed to send messages in this organization. When the user attaches the PDF file, a MailTip appears to alert the sender of this concern. The sender can decide to wait to send the message, clean out his or her mailbox, or resolve the problem another way.

Figure 3: Email message with a mailbox quota MailTips warning (Click image for larger view)

Recipients sometimes use automatic replies to advise senders that they aren't able to address new messages at the current time; however, that auto reply doesn't arrive until after the message is sent. Figure 4 shows an email addressed to a recipient that has the Automatic Reply feature enabled when MailTips comes into play. The MailTip is displayed above the address section of the new message. You can read the auto reply before you've even sent the message, so you can assess whether to send the message to another person without sending to the recipient you initially intended.

Figure 4: Email message with an automatic reply MailTips warning (Click image for larger view)

MailTips are informational; they're not enforcement mechanisms. They were designed to let the sender foresee circumstances for which he or she might want to make amendments prior to sending a message. Although they can empower preemptive efficiencies for many users, others could become immune to the information MailTips provide. To be successful, you need to make paying attention to MailTips a habit.