One of the cool features that I liked in Exchange 2010 is MailTips. If you have a question on your mind about its usability then you must have been some embarrassing moment at least once in your whole professional career just because you added an unintended recipient into the recipients of some email.

I have also seen some employees been badly scolded by their bosses for mistakes like sending some confidential or sensitive information to a DL which consists all users in the organization.

Another scenario, you are trying to send an email to a huge number of individual recipients and some of them have already left the company and don’t have their mailboxes active anymore. In such case your mailbox may get flooded with NDRs for not found user mailboxes. In other words, additional work for Exchange.

How MailTips can help is by warning or providing you information before you send an email. It can actually help you or users in  your organization by many means. In this post you will learn MailTips and its configuration.

MailTips configuration and management has some constraints you may want to understand before you configure it. Microsoft already has an article published on it here : Understanding MailTips

Consideration:

Few of the things you should know about MailTips:

• No GUI to configure or administer it. You must use Exchange Management Shell to do it.
• MailTips configuration is an organization wide configuration so you must be a member of “Organization Configuration” management role type.
• MailTips are customizable and can be configured per your need.
• Only supported clients are Outlook Web App and Outlook 2010.
• MailTips can be customized based on the requirement.
• MailTips can be used as automatic replies in stead of having an automatic reply rule configured in a mailbox. E.g. In stead of configuring an automatic reply for helpdesk mailbox you can configure a mail tip to let sender know that his ticket will be attended shortly.
• An email addressed to a distribution group will not show the MailTips configured for individual mailboxes within that DL, however, if the DL contains external recipients the MailTips indicating the number of external recipients is displayed.
• Mail tips architecture is based on Client CAS MBX relationship where client to CAS communication happens through the web services and CAS to MBX over the RPC it may badly impact the performance of the servers. To reduce the performance hit on any of the servers MailTips are designed to show individual tips for 200 recipients only. Any recipient added after 200th recipient will not be considered.
• Custom MailTips are limited to 250 characters. If you want to configure MailTips for some mailbox specifically you need to consider this. MailTips text should be lesser than 250 characters in length.
• MailTips can be enabled for individual recipients like mailboxes, contacts, mail enabled user objects, distribution groups, and public folders.
• MailTips for groups work on Group Matrices which also extends the support of MailTips for cached mode users.

Organizational Configuration of MailTips:

As stated above, there is no GUI to configure mail tips and you need to be a member of organization configuration management role.

1. You can simply open the Exchange 2010 Management Shell and execute the following command.

Set-OrganizationConfig -MailTipsAllTipsEnabled $true

This enables mail tips for the whole organization with default settings. The next job is to modify the settings as per the requirement.

2. Mail tips for external recipients are not enabled by default and you will have to enable them manually. This is completely dependant of your decision if you want to let your users know that they have added external users.

Set-OrganizationConfig -MailTipsExternalRecipientsTipsEnabled:$True

3. If you want to enable the support of mail tips for cached mode users even when they are not connected to Exchange mailboxes you need to configure the group matrices for it.

Set-OrganizationConfig -MailTipsGroupMetricsEnabled:$True

4. You can also configure the threshold for large audience. This setting is set to 25 by default and is customizable.

Set-OrganizationConfig -MailTipsLargeAudienceThreshold 100

5. In the middle section of this post you might have noticed that the mail tips can be configured for each recipient type listed above. If you want these mail tips to be visible to the clients then settings for it must be manually enabled.

Set-OrganizationConfig -MailTipsMailboxSourcedTipsEnabled $true

6. Test the configuration if that is working correctly. As per the configuration above default mail tips will be displayed, if the recipients are more than 100 then a mail tip indicating so should be displayed, if there are any mailbox specific mail tips set then they should be visible.

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