This very interesting looking feature in the next Exchange Server version is called MailTips. The idea behind MailTips is to give users information about the status of their recipients before they even start to construct the e-mail. It is intended to help prevent scenarios whereby you would send an e-mail to a colleague in another office, only to receive an out-of-office auto reply shortly afterwards saying that he or she is away on holiday for a few weeks. If you knew this information from the start you could have directed the e-mail to someone else instead, or waited till that person returned from holiday.

The rest of this article is dedicated to describing the MailTips feature and what to expect from it. First, we'll take a look at what MailTips are:

• Out-of-office auto replies
  If you know that the person you are about to send an e-mail to is out of the office, you probably won't send the e-mail to begin with. This will save you and the recipient both time and mailbox space. The image below shows this MailTip in action.

• Large Recipient List
  When sending an e-mail to a large number of recipients, such as a distribution list, a MailTip will warn you of the amount of users you are about to send the e-mail to. This will probably make you think twice before sending an e-mail to 300 people asking if they know how to get to the closest GAP store!

• BCC reply-to-all protection
  MailTips will warn you when you are about to reply-to-all on a message that was BCCed to you. This can often prevent some rather embarrassing situations. After all, BCCed recipients are normally meant to stay invisible to the rest of the recipients.

• External recipients
  This MailTip is optional and can be disabled organization wide via PowerShell (I'll explain how later in this article). It basically warns you if any of the recipients you are sending to are external or not. To be fair, unless you have a very strict e-mail policy, in most companies it wouldn't matter if you sent an e-mail to someone outside of the organization.

• Full mailbox
  This MailTip lets you know whether the recipient's mailbox has enough capacity to receive your message.

• Oversized messages
  A warning will be displayed if the message you are composing exceeds size limits set by your Administrator.

• Restricted recipient
  MailTips will tell you straight away if you don't have permission to send to a particular mailbox or distribution list (as shown in the image below).

• Invalid recipient
  This MailTip informs you whether the mailbox to which you are about to send an e-mail still exists. In Exchange 2007 and earlier, if you send an e-mail to someone whose mailbox has been disabled or deleted, you'd get a non-delivery report. This MailTip helps prevent that, for example it is particularly useful when trying to send an e-mail to someone who left the company.

• Moderated group or mailbox
  Moderated groups is another feature in Exchange 2010 that allows Administrators to control mail flow to specific distribution groups or mailboxes. This MailTip will inform you that you are sending to a moderated group or mailbox, meaning your e-mail will not be delivered until someone approves it.

Configuring MailTips through PowerShell

MailTips is enabled by default on the Exchange Organization. To view the MailTips configuration through the PowerShell, use the following cmdlet:

Get-OrganizationConfig | ft *MailTips*

When you do this you will notice that the MailTipsExternalRecipientsTipsEnabled option is set to False. This means that it will not warn you about sending to external recipients. To enable this option, use the following cmdlet:

Set-OrganizationConfig -MailTipsExternalRecipientTipsEnabled $true

Configuring MailTips through the Exchange Control Panel (OWA)

MailTips can also be configured on an individual user basis from the Exchange Control Panel portion of the Exchange Web App (aka Outlook Web Access). To configure MailTips on the mailbox of multiple individual users, do the following:

1. Login to the Exchange Web App as an Administrator

2. Click on Options to be taken to the management section of the Exchange Control Panel, then select My Organization from the drop down list near Select what to manage

3. Click Users & Groups and then the Mailboxes tab

4. Select the mailbox you want to configure and press Details to bring up the Mailbox properties window

5. Expand the MailTip option to create a MailTip that people will see when they send an e-mail to this mailbox, as shown in the image below. Here we are configuring the MailTip for the user Kenneth Spiteri. As part of this example, we also configure it for another user called Raymond Spiteri.

Now, when people try to send an e-mail to either Kenneth or Raymond they will be presented with the MailTip stating "I am just back from two weeks vacation so I apologize for the delayed response!", as shown below:

In addition to Mailboxes, MailTips can be configured from the Exchange Control Panel for Public Groups and External Contacts too (considering that you have the necessary permissions).

Performance

Performance is a major factor in server management and if you are concerned that your Exchange Server will take a hit with MailTips enabled, according to the Microsoft Exchange Team, preliminary tests have shown a less than 5% increase in load. When choosing whether to enable or disable this feature, it's all about finding the right balance between convenience and performance, but with less than a 5% increase in load I'm sure most people will see how the pros outweigh the cons.

MailTips keeps up-to-date information stored in a client side cache. Data for mailbox full and automatic replies is kept up-to-date for the last 2 hours. To clear the cache you simply need to restart Outlook or OWA. The rest of the MailTips have a default client side cache expiry of 24 hours.

Other Considerations

The downside of this new feature is that it does not work with older versions of Outlook. You'll need Outlook 2010 or the OWA version that comes with Exchange 2010 in order to make use of it.

Exchange 2010 is due out later this year and while MailTips will be available in OWA, it probably won't be before Outlook 2010 is released in H1 2010 that the entire organization will be able to experience the true benefit of this new feature.

Conclusion

MailTips promise to be a really useful new feature in Exchange 2010, as Microsoft tries to help give users a better e-mail experience and increase convenience and productivity. For those people who use e-mail every day, it wouldn't take them long to see the benefits this new feature can offer. Thumbs up to Microsoft for this one. We look forward to the 2010 release of the Microsoft Exchange and Outlook family.

References

Microsoft Exchange Team Blog: Introducing MailTips