Are you frustrated with colleagues not being careful about who they send company information? Not necessarily sensitive data—and not even necessarily to unintended recipients—but rather, sending a too-large email to too many recipients. Well, MailTips can help you avoid that ever-so-slightly uncomfortable moment when someone hits Reply All to an email that included not only the customer but also (in the reply-thread) some choice, inappropriate language regarding the customer.
The first step to enable MailTips on the back-end is to make sure MailTips are enabled for messages destined to external recipients. In PowerShell, execute the following:
Get-OrganizationConfig | Select Mailtips*
If MailTipsExternalRecipientsTipsEnabled is set to False, execute the following to enable it:
Set-OrganizationConfig -MailTipsExternalRecipientsTipsEnabled $true
Once that’s done, your users will be notified that messages with external recipients are in the distribution. It won’t stop the user from sending the messages, but it will at least give them a heads-up that the message they’re about to send is going to recipients outside of the organization.
But what about providing users something more informative? As you saw from the Get-OrganizationConfig | Select Mailtips* command you can set a threshold at which a notification is enabled based on a specified number of recipients. The default is 25, but this can be changed to a lower (or higher) number. Execute the following to change the threshold, changing the default from 25 to 30, or the required level.
Set-OrganizationConfig -MailTipsLargeAudienceThreshold 30
The next step is to get a little more granular with the warnings. Perhaps you have a distribution list that contains people from whom you need a response but who may not be able to respond in a timely manner. Setting a MailTip such as the one in the image below will alert the sender that the desired response may not be immediately forthcoming.
*Top Tip: If you are in an Exchange hybrid environment you need to execute this command on the on-premises Exchange server, not directly within Office 365.
If you’re interested, you can find the notification you just entered within Active Directory. Look for attribute “msExchSenderHintTranslations” on the properties of the group, or in ADSIEDIT and you will see the data entered above appears with HTML tags. So, when the text is synchronized to Office 365 it appears in the MailTips box like this:
<html> <body> This message is destined for the technical consultants within the company. Responses may be delayed as the recipients could be on site with customers. </body> </html>
Now, when you create a message, end enter the distribution group into the ‘To’ box, the information will be shown in a bar at the top of the message. The same will appear in Outlook. Note however that it will take up to 30 minutes to synchronize the data from Active Directory through Azure AD Connect. It will also take a second or two for the message to appear once the distribution group has been input.
Even messages sent to a Dynamic Distribution Group can be given a MailTip. In the example shown below, the message is both one that will be approved (or otherwise) by a moderator before delivery, as well as populating the membership based on a text string in Custom Attribute 2.
*Top Tip: Dynamic Distribution Groups are created in Office 365 rather than through the on-premises hybrid server. Do not create the groups on-premises as they will not be synchronized with Azure AD Connect.
In this case, when the message is created, the user will be presented with two messages—as seen below: one to indicate the message is moderated and another with the relevant MailTip.
These are just a few examples of how to give your users a gentle reminder about things that are appropriate to send—be it a notification that messages are going to a large number of recipients, going to users outside of the organization, or the timeliness with which recipients can be expected to respond. You can do so much more, so dive in with MailTips! Finally, if your organization needs help with MailTips, or any other Exchange web service, please reach out to us. We’d love to help you get started.

Mark Arnold
Microsoft Architect
For over two decades, Mark Arnold has worked for IT outsourcing and consulting organizations in both the US and UK, leveraging Microsoft’s
infrastructure solutions for large organizations. Mark is currently a delivery architect with Anexinet, focused on Microsoft Exchange and Office 365.
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