An In-Depth Look at MS Office 365’s AI MailTips

Have you ever experienced email mishaps that completely embarrassing you? For instance, sending an email that wasn’t meant for that recipient? Or putting the wrong name in a template email? Or saying you attached something … and then completely forgetting the attachment? You’re obviously not alone. Most of us have sent out emails that we wish we could take back. Thankfully, with MS Office 365’s MailTips, something can now be done about it.

What is MailTips?

Microsoft Outlook includes MailTips, an opt-in feature that sends users alerts before they click Reply All to a large recipient list. MailTips alerts are also triggered by different actions, including sending a message to someone who is not in the office or sending sensitive details to someone who is not part of your organization.

This feature has been created to basically give you information about your message and recipient/s before you hit the send button. It’s a good reminder to check yourself before you wreck yourself.

MailTips only work’s in Outlook’s online mode. It will also only work for messages below 250 characters and with less than 200 intended message recipients. Other than that, it can be pretty nifty to have activated. Here are a couple reasons why.

Unnecessary Responses

Writing and sending a message to someone who is on vacation is a waste of time; not just for you, but for the recipient as well. They’ll have too many messages to comb through once they get back, and it’s possible yours will get buried and ignored for a few days while they try to sort out their inbox. If you have MS Office 365 installed and Outlook online, MailTips will tell you when you’re sending an e-mail to someone who is out of the office.

In addition, you will get alerts if you are sending a message to a large audience. Through this feature, you can now say goodbye to those Reply to All mistakes you keep doing unintentionally.

BCC Mistakes

One of the most common email mistakes is when someone clicks Reply to All on a message they received through BCC. Once they do, they reveal to all other recipients that received the message via BCC. MailTips will save you from these embarrassing moments by warning you when you hit Reply to All on BCC.

Recipients Outside of Your Organization

MailTips informs you if you are sending an email to an external recipient – someone whose email address is not in your organization. You have the option of turning this MailTip off if you have no concerns over external recipients. But if you’re big on security, this is a good thing to have on.


If you send a message to a distribution list or a mailbox that is restricted, MailTips will tell you by sending an alert right away.

Invalid Recipients

When someone leaves your organization, there’s a chance that their name will still be in the autocomplete list of Outlook users. Sending messages to invalid users was previously solved by a bounced message. With MailTips, you are notified up front before you send an email to a user that is no longer part of the list, saving you the time.


MS Office 365 has made it so that MailTips can be fully customized according to your needs. Admins and group owners in organizations are allowed to set custom MailTips. The purpose of this is to replace any message that might otherwise be delivered as an automatic reply.  Custom MailTips is that they can be localized so users can see the notifications in their own language.

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